School Science Lessons
Topic 16f
2019-07-27
Please send comments to: J.Elfick@uq.edu.au

16.3.5.0 Terpenes
Table of contents

See: OrganicChemistry, Biochemistry (Commercial)

16.3.5.1 Terpenes (C5H8)n

16.3.5.1a Terpenoids, isoprenoids (C5H8)n, modified terpenes

16.3.5.1b Terpinenes (cyclic terpenes) (C10H16)

16.3.5.1 Terpenes (C5H8)n
16.3.5.1 Terpenes (C5H8)n
16.3.5.02 Isoprene units (C5H8), (CH2=C(CH3)CH=CH2)
16.3.5.1.1 Hemiterpenes (C5H8), (one isoprene unit)
16.3.5.1.2 Monoterpenes (C10H16), (two isoprene units)
16.3.5.03 Iridoids
16.3.5.1.3 Sesquiterpenes (C15H24), (three isoprene units)
Sesquiterpene Lactone 16.3.5.1.4 Diterpenes (C20H32), (four isoprene units)
16.3.5.1.5 Sesterterpenes (C25H40), (five isoprene units)
16.3.5.1.6 Triterpenes (C30H48), (six isoprene units)
16.3.5.1.8 Tetraterpenes (C40H64), (eight isoprene units)
16.3.5.1.9 Polyterpenes (C5H8)n, (many isoprene units)
Steroid Saponins

Cardenolides
| Alvonal MR, Cymarine | Digitoxin | Digoxin
| Ouabain | Strophanthin |
Phytosterols
Cucurbitacins
Nortriterpenoids
Miscellaneous triterpenoids
Carotenoids

16.3.5.02 Isoprene units (C5H8)
Isoprenoids are compounds derived from isoprene, often showing repeated occurrence of isoprene units.
Isoprene, C5H8 (2-methyl-1,3-butadiene) (CH2=C(CH3)-CH=CH2), unsaturated pentahydrocarbon, colourless,
volatile, inflammable, faint hydrocarbon odor, insoluble in water, less dense than water.
Isoprene is in many foods, human breath and isoprene emission may protect plants from heat stress.
Isoprene forms the structural unit of natural and synthetic rubbers.
The 5-carbon isoprene units in natural products have a four carbon chain and a one carbon branch at C2, i.e. [C(CC)CC].
Isoprene is obtained by distillation of caoutchouc or gutta-percha.
In plants, used in the formation of isoprenoids, fat-soluble vitamins, carotenoids.
Isoprenes contribute to flavors and fragrances of essential oils.
Isoprene vapour may irritate eyes, skin and mucous membranes.
See diagram: Isoprene

16.3.5.03 Iridoids
See diagram: Iridoid molecules
Monoterpenoid lactones, in many dicotyledons, bitter tasting, large concentrations toxic, in folk medicines
Phytochemicals by trivial names

16.3.5.1a Terpenoids, isoprenoids (C5H8)n, modified terpenes
16.3.5.1a Terpenoids, isoprenoids, (C5H8)n, modified terpenes
16.3.5.1.1a Hemiterpenoids (C5H8)
16.3.5.1.2 Monoterpenoids (C10H16)
16.3.5.1.3a Sesquiterpenoids (C15H24)
16.3.5.1.3b Sesquiterpenoid lactones (C22H30O7)
16.3.5.1.4a Diterpenoids (C20H32)
16.3.5.1.5a Sesterterpenoids (C25H40)
16.3.5.1.6a Triterpenoids (C30H48) --> natural steroids
16.3.5.1.8a Tetraterpenoids, carotenoids (C40H64)
Two classes of Tetraterpenoids:
16.3.5.1.0 Carotenes (C40Hx)
16.3.5.2.0 Xanthophylls (C40H56On)
16.3.5.1.7 Apocarotenoids
Polyterpenoids (C5H8)n

16.3.5.1b Terpinenes (cyclic terpenes) (C10H16)
Three isomers:
1. Alpha-terpinene, oil with lemon smell, in cardamom, coriander, marjoram, allspice and many essential oils, e.g. Citrus, Eucalyptus
and Juniperus species, Oil of Litsea ceylanica, flavouring agent, anti-fungal
2. Beta-terpinene, no known natural source, but prepared synthetically from sabinene in oil of savin.
3. Delta-terpenine (gamma-terpinene), terpinolene (p-mentha-2, 4-diene), smoke or wood smell, in coriander, cumin, lemon, samphire,
apple, lilac, tea tree, Valencia orange oil, Rau om, antioxidant, anti-cancer, anti-fungal, anti-bacterial, sedative, repels mosquitoes.

16.3.5.1.1 Hemiterpenes, (one isoprene unit) (C5H8)
Isoprene (C5H8) is the only hemiterpene.

16.3.5.1.2 Monoterpenes, (two isoprene units) (C10H16) and Monoterpenoids
Anethofuran, C10H16O
Anethole, C10H12O
Ascaridole, C10H16O2
Bornane, C10H18
Borneol, C10H18O.
Camphene, C10H16
Camphor, DL-Camphor, C10H16O: 16.3.6.6
Carene, C10H16
Carvacrol, C10H14O, monoterpenoid phenol
Carveol, C10H16O, monoterpenoid alcohol
Carvone, C10H14O
Citral, C10H16O, monoterpenoid, Two isomers: Neral, C10H16O, Citral B, monoterpenoid
Chrysanthemic acid, C10H16O2
Chrysanthenone, C10H14O
Cineole, C10H18O, eucalyptol
Citronellal, C10H18O, monoterpenoid
Citronellol, C10H20O, acyclic monoterpenoid
Cymene, C10H14
Cuminaldehyde, C10H12O
Dimethyl-3-octanol, C10H22O
Fenchol, C10H18O
Fenchone, C10H16O
Geranic acid, C10H16O2
Geraniol, C10H18O, , monoterpenoid alcohol
Geranyl acetate, C12H20O2
Grapefruit mercaptan, C10H18S, monoterpenoid
Hinokitiol, C10H12O2, monoterpenoid,
Hydroxygeraniol, C10H18O2
Incarvillateine, C42H58N2O8
Jasmolone, C11H16O2
Lavandulol, C10H18O, monoterpenoid alcohol,
Limonene, C10H16
Linalool, C10H18O
Linalyl acetate, C12H20O2
Methane-3-8-diol, C10H20O2
Menthol, C10H20O
Menthone, C10H18O
Menthoxypropanediol, C13H26O3
Menthyl acetate, C12H22O2
Menthylisoborneol, C11H20O
Menthatriene, C10H14
Mercaptomenthone, C10H18OS
Myrtenal, C10H14O
Myrcene, C10H16
Myrcenol, C10H18O
Nerol, C10H18O
Nerolic acid, C10H16O2
Ocimene, C10H16
Perilla ketone, C10H14O2
Perillaldehyde, C10H14O
Perillartine, C10H15NO
Perillene, C10H14O
Perillyl alcohol, C10H16O
Phellandrene, C10H16
Pinene, C10H16
Pinocamphone, C10H16O
Piperitone, C10H16O
Pulegone, C10H16O,
Rhodinol, C10H20O
Rose oxide, C10H18O, monoterpenoid
Sabinene, C10H16
Sabinene hydrate, C10H18O
Safranal, C10H14O
Terpinene, C10H16
Terpineol, C10H18O
Terpinoline, C10H16
Thujene, C10H16
Thujone, C10H16O
Thymol, C10H14O
Verbenone, C10H14O
Wine lactone, C10H14O2
Iridoids are cyclic monoterpenoids having the iridane skeleton (1-isopropyl-2, 3-dimethylcyclopentane).
Iridoid monoterpenoid, C16H22O10

16.3.5.1.3 Sesquiterpenes
Sesquiterpenes (three isoprene units), C15, terpene with formula C15H24
Sesquiterpenes are hydrocarbons (terpenes) with 15 carbon atoms.
They are naturally occurring alcohols that very rarely exist as volatile oils.
Sesquiterpenes, along with monoterpenes, are an important constituent of essential oils in plants though from the same family of terpenes.
Sesquiterpenes are larger molecules than monoterpenes.
When distilled from the plant matter, these compounds stimulate glands and the liver, and have anti-allergen, antispasmodic, and
anti-inflammatory properties.
Sesquiterpenes are formed from three isoprene units.
They may be acyclic, mono-, di-, or tricyclic; synthesized from farnesyl pyrophosphate.
In turn, farnesyl pyrophophate is a pyrophosphoryl derivative of Farnesol
Sesquiterpenes are isolated from their natural sources by distillation with steam or by extraction.
They are purified by vacuum fractional distillation or by chromatography.

Abscisic acid, C15H20O4
Bergamotene, C15H24
Bisabolol, C15H26O
Cadinene, C15H24
Caryophyllene, C15H24
Cedrol, C15H26O
Curcumene, C15H22
Cyperene, C15H24
Elemene, C15H24
Farnesene, C15H24
Farnesol, C15H26O
Germacrene, C15H24
Guaiazulene, C15H18
Humulene, C15H24
Jasmalone, 2-hexylidenecyclopentanone, C11H18O
Jasmolone, C11H16O2
Juvabione, C16H26O3
Longifolene, C15H24
Nerolidol, C15H26O
Patachoulol, C15H26O
Petasin, C20H28O3
Selinene, C15H24
Vulgarin, C15H20O4
Zingiberine, C15H24

16.3.5.1.3a Sesquiterpenoids
Sesquiterpenoids (C15H24), Natural sesquiterpenoids
C15H22, Cuparene, in Perilla frutescens
C15H24, Allo-aromadendrane, woody odour, in allspice , Tasmanian gum, Eucalyptus globulus
C15H24, Alpha-bisabolene, Caryophyllane, Cedrene in essential oil of cedar
C15H24, Beta-bisabolene, balsamic odour, food additive
C15H26, Longifolane, Longipinane, Alpha-cedrane, Patchoulane
C15H28, Cadinane, cadinene, from cade oil in Juniperus oxycedrus, prickly juniper, sharp cedar
C15H28, Chamigrane, Eremophilane A and B, Eudesmane, Guaiane, Himachalane, Vetispiane (Agrospiran)
C15H30, Elemane, Germacrane, Humulane
C15H32, Farnesane (Mono-and cyclo- farnesanes).

16.3.5.1.3b Sesquiterpenoid lactones
(3 isoprene units + lactone ring)
Usually bitter taste, nonvolatile crystalline solids, some cause allergy reactions and livestock toxicity
Most are in the Asteraceae family.
List of sesquiterpene lactones
Artemisinin, C15H22O5
Chamazulene, C14H16
Deoxylactucin, C15H16O4, 8-Deoxylactucin
Helenanin
, C15H18O4
Lactucin, C15H16O5,
Lactucopicrin, C23H22O7
Matricarin, C17H22O5
Nomilin, C28H34O9
Parthenolide, C15H20O3

1. Germacranolides
Germacranolides, group of sesquiterpenoid lactones
Germacranolide, C15H22O4, in bigroot Geranium.

2. Eudesmanolides
Eudesmanolides, group of sesquiterpenoid lactones
Eudesmanolide, in Japanese bigleaf magnolia
Paludolactone, in Wedelia paludosa, creeping ox-eye.

3. Guaiaolides
Guaiaolides, group of sesquiterpenoid lactones
15-nor-guaianolide, C14H18O4, azulene sesquiterpenoid lactone, in Guaiac wood.

16.3.5.1.4 Diterpenes, (four isoprene units), C20H32
In perfumes and resins, pine turpentine, distilled essential oil,
Abietic acid, Pinus, most abundant compound in rosin
Andrographolide, C20H30O5
Bixin, C25H30O4.

16.3.5.1.4a Diterpenoids, C20
Diterpenoid alkaloids
Forskolin, C22H34O7
Retene, C18H18.

16.3.5.1.5 Sesterterpenes, (five isoprene units)
Sesterterpenes, C25, in insect waxes, fungi products, phytotoxins, geranyl, farnesol, ceroplastol, insect gascardic acid
Scalarane, C25H44
Phyllofenone, in South Seas sponge.

16.3.5.1.5a Sesterterpenoids, (C25H40)
Azafrin, C27H38O4.

16.3.5.1.6 Triterpenes C30 (six isoprene units)
Triterpenes (six isoprene units) (C30H48), C30, steroids and sterols, three terpene units, e.g. Squaline, C30H50, in sharks amaranth seed,
rice bran, wheat germ, olives, yeast cells
Squaline is the precursor of animal sterols, including cholesterol and steroid hormones
Pentacyclic triterpenes have anti-inflammatory properties.
16.3.5.1.6a Triterpenoids, C30, antioxidant properties, prevent lipid peroxidation and suppress superoxide anion generation.

Triterpenic acids
See diagram: Triterpene acids: Ursolic acid and Oleanolic acid
1. Ursane type, C30H52, e.g Ursolic acid, C30H48O3, pentacyclic triterpene acid, isomer is oleanolic acid
See diagram: Ursane
Ursolic acid, C30H48O3, pentacyclic triterpenoid, in basil, bilberry, cranberry, elder flower, epicuticular apple wax, four o'clock flower,
ground ivy (alehoof), hawthorn, holy basil, lavender, loquat, oregano, peels of fruits, peppermint, prunes, rosemary, thyme, weeping
paperbark, antitumor, antioxidant, regulating the apoptosis induced by high glucose, affects growth and apoptosis in cancer cells.
See diagram: Ursolicacid
2. Oleanane type, C30H52, e.g. Oleanolic acid, C30H48O3. pentacyclic triterpene
See diagram: Oleane
Oleanolic acid, C30H48O3, pentacyclic triterpenoid, in olive oil, honey mesquite, garlic, java apple, cloves, American pokeweed,
Hyptis species (bushmints), Syzygiumspecies.
Oleanolic acid is the free acid or the aglycone for many saponins, pro- and anti-inflammatory, modulating the immune response.

16.3.5.1.6a Triterpenoids, C30, any terpenoid derived from triterpene
Azadirachtin, C34H44O16
Betulinic acid, C30H48O3
Gammacerane, C30H52, triterpenoid
Hederagenin, C30H48O4
Lupeol, C30H50O
Oleanolic acid, C30H48O3
Squalene, C30H50
16.3.5.1.6b Tests for saponins
Ursolic acid, C30H48O3.

Triterpenoid saponins in legumes, maize, alfalfa,
1. Alpha-hederin, Araloside A, Astragaloside, Bacoside A, Cucurbitacin, cytotoxic, 2. Cucurbitane, C30H54, in Cucurbitaceae
3. Eleutheroside, Ginoside, Gynpenoside, 20-hydroxyecdysone, Soyasapogenol B, C30H50O3
4. Tangshenoside I, Tinosporide,
5. Withanosides, C40H62O15
Steroidal sapogenins:
6. Tigogenin (C27H44O3), steroidal saponin, in Trigonella foenum-graecum, fenugreek
7. Digitonin (C56H92O29), steroidal saponin, in Digitalis purpurea, foxglove
8. Dioscin (C45H72O16), steroidal saponin, treat liver injury, potential anticancer, antifungal, in Dioscorea nipponica
9. Gitonin (C50H82O23), steroidal saponin, in Digitalis purpurea, foxglove
10. Sarsasapogenin (C27H44O3), in Smilax aspera, Spanish sarsasparilla.

Sapogenins are the non-saccharide (aglycone) part of saponin glucosides, e.g. the steroidal sapinigen,
Sapogenins are derivatives of triterpenoids or steroids, oxygenated C27 steroids
Digitogenin (C27H44O5), sapogenin, hydroxy steroid
Diosgenin (C27H42O3), steroid sapogenin, in Costus speciosis, Dioscorea species, wild yam
Gitoxygenin (C23H34O5)
Tiggenin, in Chlorophytum borivilianum
Yamogenin (C27H42O3), sapogenin, in Trigonella foenum-graecum, fenugreek

16.3.5.1.6b Tests for saponins
Add ground plant material to test-tube of water, heat to boiling, add stopper and shake the test-tube.
Note presence of stable froth.

16.3.5.1.8 Tetraterpenes C40 (eight isoprene units)
Tetraterpenes, C40 (eight isoprene units), C40H56, carotenoid pigments, e.g. alpha-carotene, C40H56, beta-carotene C40H56.
alpha-carotene and beta-carotene, their derivatives, tetraterpenoids, are terpenoids of 8 isoprene units, 40 carbon atoms in the skeleton.

16.3.5.1.8a Tetraterpenoids, Carotenoids, tetraterpene derivatives
1. Carotenoid pigments are tetraterpenoids derived from the acyclic parent carotene, produced from 8 isoprene molecules and have 40
C atoms, in two six-carbon rings connected by a chain of carbon atoms.
2. Carotenoids are red, orange and yellow, fat-soluble, insoluble in water, plant and animal organic pigments in plants, some algae, some
fungi and some bacteria, e.g MRSA (Methicillin-resistant Staphylococcus aureus) to protect themselves from immune attack.
3. Presence of carotenoids is shown by the bright red, orange and yellow pigments
In beet greens, broccoli, cantaloupe, carrots, collard greens, green peas, kale, leafy green vegetables, mango, okra, oranges, papaya,
parsley, pink grapefruit, pumpkin, red peppers spinach, sweet potatoes, Swiss chard, tangerines, tomatoes, watermelon, winter squash,
and fish liver oil.
4. Carotenoids should be ingested with fats in the diet and are stored in fatty tissue, may be antioxidants and a high carotenoid diet may
help reduce the risk of lung cancer in non-smokers and breast cancer
Most carotenoids are not damaged by cooking.
5. Carotenoids absorb blue and green wavelengths of light causing yellow and orange colours.
Carotenoids occur in chromoplasts which show when fruit is ripe and in chloroplast membranes to absorb light energy for photosynthesis,
as accessory pigments and to protect chlorophyll from damaging wavelengths.
The most common carotenoids in food are alpha-carotene, beta-carotene, beta-cryptoxanthin, lutein, zeaxanthin, and lycopene.
6. Provitamin A carotenoids, alpha-carotene, beta-carotene, and beta-cryptoxanthin, can be converted to retinol (vitamin A).
Lutein and zeaxanthin, in the macula of the eye, absorb most incident blue light, and may prevent age-related macular degeneration.
7. Carotenoids can be classified depending on the presence or absence of oxygen.
Carotenoids are divided into carotenes and xanthophylls.
16.3.5.1.0 Carotenes, C40Hx
16.3.5.2.0 Xanthophylls, C40H56On.

16.3.5.1.9 Polyterpenes (many isoprene units)
Polyterpenes contain a long chain of thousands of C5H8 isoprene subunits in milky latex sap: 1. Rubber, 2. Gutta-percha, 3. Chicle.

1. Rubber
Rubber, latex (C5H8)n, [n = 4, 0005, 000], trans-1.4-polyisoprene, cis double bonds, from latex of: (Hevea brasiliensis), and (Ficus elastica),

2. Gutta-percha
Gutta-percha, polyterpene, natural polymer, trans-1.4-polyisoprene, trans double bonds, from latex of: Palaquium gutta, and other species.
Isoprene is produced by distillation of gutta percha.

3. Chicle
Chicle, polyterpene, from the sapodilla tree (Manilkara zapota), used for chewing gums.
Norisoprenoids, C13, Vitis vinifera.

16.3.5.1.0 Carotenes (C40Hx)
Boiling, test the cooking water of boiled vegetables: 19.3.3 (See 1. and 6.)
Carotenoids, Tetraterpenoids: 16.3.5.1.8a
Cells, plant cells, Elodeas: 9.9.0 (See: Chromoplasts)
Chromatography of chlorophyll pigments: 6.5.5
Margarine: 19.2.1.10
Separate by chromatography, pigments from green leaves: 3.24.0
Vitamin A: 16.4.1.01.

Carotenes, C40Hx, are hydrocarbons, so contain no oxygen, in green, yellow and leafy vegetables.
Lycopene
, C40H56
Phytoene, C40H64
Phytofluene, C40H62
Neurosporene, C40H58.
Carotenoids Fucoxanthin, Lycopene, Retinoic acid, Retinol
Carotenes, C40H56
Alpha-carotene (α-carotene), C40H56, carotenoid pigment
Beta-carotene (β-carotene), C40H56, carotenoid pigment, from lycopene, terpenoid, most common form of carotene, red-purple oil,
not soluble in water, in coloured fruits and vegetables, from lycopene.
Dark orange varieties of sweet potato contain beta carotene.
Gamma carotene (γ-carotene), Gamma carotene (γ), C40H56, carotenoid pigment, from lycopene
E160a
Carotenes
E160e, Beta-apo-8' carotenal,
E160f, Ethyl ester of beta-apo-8
Carotenes are hydrocarbon carotenoids, a subclass of tetraterpenes and C5n polyterpenes.
Plants rich in carotenes include: Sweet potato (red variety) (9, 507 μg in 100 g), Kale (9, 226 μg in 100 g), Carrot (8, 285 μg in 100 g),
Mustard greens (6, 300 μg in 100 g), Spinach (5, 626 μg in 100 g), Dried basil (5, 584 μg in 100 g), Butternut squash (4, 570 μg in
100 g), Lettuce (red leaf variety) (4, 495 μg in 100g).
β-Carotene, Type I, synthetic, 93% (UV), powder, β, β-Carotene, Provitamin A, C40H56
β-Carotene, Type II, synthetic, 95% (HPLC), crystalline, β, β-Carotene, Provitamin A, C40H56.

16.3.5.2.0 Xanthophylls
Cells, human cheek cells, Elodea plant cells: 9.9.0
Chromatography of chlorophyll pigments: 6.5.5
Eggs in your diet: 9.00
List of xanthophylls
Separate pigments, leaves, chromatography: 3.24.

Xanthophylls, C40H56On, are hydrocarbons + oxygen, and are usually yellow pigments
Xanthophylls, contain oxygen, usually yellow pigments, in the leaves of most plants.
Xanthophylls are oxygenated carotenes, the yellow leaf pigments of leaves, synthesized within plastids without need for light for
synthesis, but do absorb some wavelengths not absorbed by chlorophyll, so appear in etiolated leaves and plants with chlorosis nutrient
deficiency.
In leaves of most plants, often yellow, with carotenoid pigments when leaves turn orange in autumn, involved in photosynthesis with
green chlorophyll, which covers up the yellow except during autumn.
Colours, food colours, food additives.

List of xanthophylls
Antheraxanthin, C40H56O3
Astaxanthin, C40H52O4
Canthaxanthin, C40H52O2
Capsanthin, C40H56O3
Cryptoxanthin, C40H56O
Flavoxanthin, C40H56O3
Lutein, C40H56O2
Neoxanthin, C40H56O4
Rhodopin, C40H58O
Rhodoxanthin, C40H50O2
Rubixanthin, C40H56O
Staphyloxanthin, C51H78O8
Violaxanthin, C40H56O4
Xanthophyll from marigold
Zeaxanthin, C40H56O2.

16.3.5.1.7 Apocarotenoids
Apocarotenoids (C<40), Derived from carotenoids by oxidative cleavage
9.1.7.5 Abscisic acid, C15H20O4, isoprenoid plant hormone, guard cells
Apocarotanal, C30H40O
Bixin, C25H30O4
Crocetin, C20H24O4
Crocin, C44H64O24
Peridinin, C39H50O.

16.3.5.1.1a Hemiterpenoids, C5.
Prenol, C5H10O
Isovaleric acid, C5H10O2.

Abscisic acid
Abscisic acid, C15H20O4, sesquiterpene, cyclic sesquiterpene (ABA), dormic acid (DMA), plant hormone
Abscission-accelerating plant growth substance, in young cotton fruit, leaves of sycamore, birch, potatoes, lemons, avocados.
9.1.7.5 Abscisic acid, C15H20O4, Avarol.

Ambrein
Ambrein, C30H52O, a triterpene alcohol, is the main constituent of ambergris found in the sperm whales or floating on the sea as
whale barf (vomit), whale spit.
It is supposed to protect the intestines of whales from the sharp beaks of cuttlefish.
It was used for food flavouring and in the perfume industry to prevent aroma from dissipating too quickly.
Since 1970 the perfume industry has turned to substitutes to protect whales.
It is supposed to be an aphrodisiac.

Andrographolide
Andrographolide, C20H30O5, labdane diterpenoid, andrographolide lactone, extremly bitter, anti-inflammatory, anti-platelet aggregation,
decreased proliferation of tumor cells and increased immunocytotoxicity against them.
Andrographis paniculata Extract (HMPL-004) is used to treat bacillary dysentery, upper respiratory tract infections, inflammatorydiseases.
Andrographolideoc occurs in Andrographis paniculata.
See diagram: Andrographolide

Anethofuran
Anethofuran, C10H16O, monoterpene ether, dill ether, flavouring agent, colorless to pale yellow clear liquid, up to 20% in dill leaf oil, in | Caraway | Dill |.

Antheraxanthin
Antheraxanthin, C40H56O3, , xanthophyll carotenoid, oil-soluble alcohol, bright yellow accessory pigment, in Capsicum.
See diagram: Antheraxanthin

Artemisinin
Artemisinin, C15H22O5, sesquiterpenoid lactone, artemisene, qinghaosu, ancient Chinese herbal medicine, used to treat malaria, including
chloroquine-resistant Plasmodium falciparum, using artimisin-combination therapies (ACTs), and antihelmintic, schistosomiasis
possibly colo-rectal cancer, may damage liver, once used in the production of absinthe and nowadays flavours some vermouths,
in Sweet wormwood.

Astaxanthin
Astaxanthin, C40H52O4, keto-carotenoid terpene pigment (ketone), red, a xanthophyll but it is a carotenoid with no vitamin A activity,
in most red-coloured aquatic organisms, microalgae, yeast, salmon, krill, crabs, fish feed, red pigment of exoskeletons of crustaceans,
egg yolks, red fish, fruits and vegetables, food dye, Food colour additive E161j, found to to mediate anti-oxidant and anti-inflammatory
actions, prevents Alzheimer's disease, cold and influenza, protect the iris from sunlight and protect skin cells from ultraviolet rays.
See diagram: Astaxanthin

Ascaridole
Ascaridole, C10H16O2, bicyclic monoterpene, natural organic compound, colourless liquid, soluble in most organic solvents,
unstable and may explode when heated or treated with organic acids, pungent smell, antihelminthic, in cardamom, tea tree oil,
major constituent of oil of Peumus boldus (boldo) and Dysphania ambrosioides (Mexican tea, epazote).
Boldo.

Azadirachtin
Azadirachtin, C34H44O16, triterpenoid, yellow-green powder, strong garlic/sulphur odour, tetranortriterpenoid, natural pesticide, in Neem tree,
Azadirachta indica, Meliaceae.
See diagram: Azadirachtin

Azafrin
Azafrin, C27H38O4, escobedin, sesterterpenoid, in Azafranillo, Escobedia scabrifolia, Scrophulariaceae.

Bergamotene
Bergamotene, C15H24, sesquiterpene, alpha-bergamotene, polycyclic olefin, contains volatile oils, pale green clear liquid, woody
odour, not used for fragrance or flavour
in Kumquat | Cinnamon | carrot oil | Bergamot orange | Key lime (lime) | Citron
16.3.3.0 Furanocoumarin, furocoumarin.

Betulinic acid
Betulinic acid, C30H48O3, betulone, deltonin, isobrucein, moronic acid, picrasin, triterpenoid, pentacyclic triterpenoid,
anti-inflammatory, antimalarial, anti-HIV and antineoplastic, induces apoptosis through induction of changes in mitochondrial membrane,
cytotoxic against non-melanoma tumor cell types, cardiovascular role, derivative of betulin and isolated from the bark of Betula alba
the common white birch, the Ber tree (Ziziphus mauritiana), tropical carnivorous plants Triphyophyllum peltatum and
Ancistrocladus heyneanus, Diospyros leucomelas, Tetracera boiviniana, the jambul (Syzygium formosanum),
flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis.
See diagram: Betulinic acid

Bisabolol, natural complex alcohol
Bisabolol, C15H26O, sesquiterpene (bisabolane), monocyclic sesquiterpene alcohol
essential oils from leaves alpha-bisabolol used for skin healing, in leaves of Hymenocrater yazdianus extracted from German chamomile.
See diagram: Bisabolol

Bixin
Beta-bixin, C25H30O4, carotenoid pigment, diterpene (apocarotenoid) (colour: yellow to pink) (Health risk, allergic-type
reactions, hyperactivity, head banging, skin irritation), used as body paint, fabric dye pigment, in Bixa orellana (achiote,
lipstick tree), E160b Annatto food additive, peppery aroma and flavour, annatto is a natural
food colouring but linked with food-related allergies, "all natural" or "no artificial colors", Annatto also called Roucou, derivative >
Bornane
Bornane, C10H18, terpene, camphane, bornylane, crystalline, saturated, "parent compound" of borneol and camphor, in
Camphor laurel tree.

Borneol
Borneol, C10H18O, bicyclic monoterpene, terpene derivative, Borneo camphor, white lump, camphor-like odour, strongly aromatic
mint, spicy, cooling scent, pungent, bitter, slightly cold, denser than water, used in perfumes, traditional Chinese medicine, antipyretic,
analgesic, anti-inflammatory, used to treat "obstruction of orifices", heat syndromes, pain, throat swelling, mouth sores, ear and eye
infections, analgesia, anaesthesia, high concentration in camphor laurel, rosemary, mint, in | Mugwort | Dryobalanops aromatica |
Blumea
balsamifera | Coriander | Hyssop | Ginger | Wild tumeric |.

Cadalene
Cadalene, C15H18, sesquipertene derivative, cadalin, polycyclic aromatic hydrocarbon, in essential oils many plants, e.g. Pinaceae.

Cadinene
Cadinene, C15H24, sesquiterpene, bicyclic sesquiterpene, beta-cadinene, in Juniperus oxycedrus.
Capsidiol in tobacco, chilli after infection.

Cafestol
Cafestol, C20H28O3, diterpene, in coffee bean oil, anti-inflammatory, associated with some natural cell death, some cardiotoxic
conditions and some high levels of cholesterol in the blood, chemoprotective against some carcinogens, stimulates insulin secretion and
so contributes to prevention of type 2 diabetes, T2D.
in Coffee (Caffea arabica), Rubiaceae.
Casbene, C20H32, casbene synthase enzyme
Cembrene, Nicotiana, Pinus
Gibberellin (phytohormones and germination), gibberellin A1, gibberellin plant hormones, causes stem elongation
Podocarpic acid (disease resistance),
Retinol, C20H30O, diterpenoid alcohol, Vitamin A activity: 16.4.1.01
Sclarene, C20H32.

Camphene
Camphene, C10H16, bicyclic monoterpene, colourless to white crystals, almost insoluble in water, pungent camphor smell, when
heated emits irritating flammable vapours and acrid smoke, used to manufacture synthetic camphor for insecticide moth balls, produced
synthetically from oil of turpentine, store in cool dark place tightly sealed containers protected from heat and light.
In camphor laurel, carrot, dill, fennel, tarragon, marjoram, thyme, nutmeg, parsley, pepper.

Canthaxanthin
Canthaxanthin, C40H52O2, keto-carotenoid pigment (ketone), terpenoid, antioxidant, pink
keto-carotenoid (from β-carotene or animals, e.g. crustaceans
E161g: Canthaxanthin food additive
In paprika, algae, lobsters, fish and chanterelle mushrooms, farmed salmon feed.
Canthaxanthin is a lipid-soluble antioxidant that may protect cells from ultraviolet rays, and so may be an ingredient in sunless tanning
products, but these products can be very dangerous leading to vision and skin colour disorders, artificial tanning produces orange skin.

Capsanthin
Capsanthin, C40H56O3, keto-carotenoid pigment (ketone)
E160c: Capsanthin food additive, Paprika extract, Capsorubin.

Capsidiol
Capsidiol, C15H24O2, bicyclic terpene, occurs in tobacco Nicotiana tabacum, chili pepper Capsicum annuum, forms in response to
fungal infection.

Capsorubin
Capsorubin, C40H56O4, keto-carotenoid pigment (ketone)
E160c: Capsorubin food additive, Paprika extract, Capsanthin, red paprika pigment.

Carene
Carene, C10H16, bicyclic monoterpene, delta-3-carene, sweet, pungent odour, alpha-carene flavouring ingredient, in allspice, cedar,
rosemary, Turpentine tree.

Citranaxanthin
Citranaxanthin, C33H44O, carotenoid pigment, yellow food dye (apocarotenoid from cleavage of carotenoid).
E161g: Citranaxanthin food additive.

Cryptoxanthin
Cryptoxanthin, C40H56O, carotenoid pigment, in yellow maize, orange and red pumpkins and chillies
Alpha-cryptoxanthin, C40H56O
Beta-cryptoxanthin, C40H56O, carotenoid pigment, antioxidant, inhibits urinary bladder cancer, provitamin A: 16.4.1.01
Cryptoxanthin is an antioxidant that may improve vision and night vision and bone growth and prevent arthritis, but deficiency may cause
dry skin, and vision problems.
Cryptoxanthin, C40H56O, β-Cryptoxanthin, provitamin A: 16.4.1.01 (See: 4.)

Capisterone
Capisterone A and B, C32H50O8S from marine algae.

Carvacrol
Carvacrol, C10H14O, monoterpenoid phenol, cymophenol, antioxidant, C6H3CH3(OH)(C3H7), 5-isopropyl-2-methylphenol, aromatic
monoterpene, flavouring agent, gives "penetrating" flavour to some varieties of oregano, in black walnut, in Labiateae, thyme oil,
origanum oil, may protect against prostate cancer
See diagram: Carvacrol.

Carveol
Carveol, C10H16O, monocyclic monoterpene, p-mentha-6, 8-dien-2-ol, monocyclic monoterpenoid alcohol, terpene alcohol,
flavouring agent, food additive, antiparasitic, anticancer (breast cancer), food additive fragrance, in orange and grapefruit juice,
kumquat and pommelo peel oil, caraway seeds, cis-carveol in Spearmint, in oil of grapefruit, mandarin, blackcurrant, celery, black tea,
caraway seed, Lamb's lettuce
JECFA 381 Flavouring agent.

Carvone
Carvone, C10H14O, monocyclic monoterpene, volatile terpenoid ketone, colourless to slightly yellow liquid, prevents potatoes sprouting,
mosquito repellent, very abundant in caraway seed, and in dill, spearmint, costmary, kuromoji and other oils, ancient Roman medicine
Flavouring agents:
D-carvone [(R)-Carvone] has Caraway odour.
L-carvone [(R)-Carvone] has Spearmint odour.
Carvonic acid, C10H12O3, terpenoid from carvone.
See diagram: Carvone

Caryophyllene
Caryophyllene, C15H24,iso-carryophylene, bicyclic sesquiterpene in two main forms:
1. beta-caryophyllene, BCP, 2. trans-caryophyllene, TC.
BCP is widespread in plants and is a major constituent in essential oils of oregano, cinnamon, black pepper,
also in cloves, hops, rosemary, basil, marjoram, peppermint, spearmint and hemp (Cannabis sativa).
BCP is a pale yellow oily liquid with a clove-turpentine, weak aromatic taste, gives black pepper a spicy
woody flavour, and is used as a food additive and in cosmetics.
BCP is a dietary cannabinoid, a major component in hemp Cannabis sativa
Cannabinoids, compounds closely related to cannabinol and the active constituents of cannabis, are usually
anti-oxidant, anti-inflammatory, anti-cancerous, and local anesthetics. so BCP is possibly anti-cancerous.
Caryophyllene, C15H24, bicyclic sesquiterpene, 3 isoprene units, contains a
cyclobutane ring (CH2)4
See diagram: Caryophyllene
Caryophyllene oxide, isolated from unsaponified petroleum ether extract of the bark of Annona squamosa,
has been studied for its analgesic and anti-inflammatory activity

Cedrol
Cedrol, C15H26O, sesquiterpene alcohol, essential oil of conifers, cedarwood oil, in Cupressus and Juniperus.

Chamazulene
Chamazulene, C14H16 (1, 4-dimethyl-7-ethylazulene), sesquiterpene lactone, dimethulene, in deep blue chamomile oil of chamomile
flower (German chamomile), chamomile extracts are anti-inflammatory by inhibiting the CYP1A2 enzyme, antioxidant, anti-allergenic.
Chamazulene can be isolated from sequiterpene oils of | Anise | Chamomile |See diagram: Chamazulene
Mugwort | Sneezewort | Wormwood | Yarrow |
sesquiterpene lactone matricin, C17H22O5 --> azulene, C10H8 ---> chamazulene, C14H16.
See diagram: Chamazulene

Chrysanthemic acid
Chrysanthemic acid, C10H16O2, causes skin and eye irritation, related to pyrethrin insecticides in Chrysanthemum.

Chrysanthenone
Chrysanthenone, C10H14O, terpene, 2-pinene-7-one, from isoprene.

Cineole
Cineole, C10H18O, 1, 8-cineol, eucalyptol, natural monoterpene, cyclic ether
Eucalyptol, colourless liquid, inhibits plant growth, paint stripper, adhesive, solvent, sticky spot remover, flavouring, camphor-like odour,
spicy cooling taste, additive to cigarettes to improve the flavour, fragrance, mouthwash, anti-inflammatory, releases vapours for medical
use, useful for getting chewing gum out of children's hair and turning stuck nuts and bolts, in many aromatic plants, and their essential
oil fraction, some deaths was reported after ingestion of essential eucalyptus oil
Eucalyptus odour, in Eucalyptus globulus, in Basil
Zedoary Oil, essential oil from rhizome of Curcuma zedoaria known as zedoary, contains eucalyptol, used in treatments for digestive
disorders, has cytotoxic effects on non-small cell lung carcinoma and causes cancer cell apoptosis.
E zhu (Curcuma zedoaria), Zingiberaceae.

Citral
Citral, C10H16O, monoterpenoid, geranialdehyde, lemonal, 3, 7-dimethyl -2, 6-octadienal, aliphatic aldehyde, clear yellow coloured
liquid, lemon-like odour, bittersweet taste, less dense than water, about 0.9 g/cm3, and insoluble in water, toxic by ingestion, flavouring
ingredient, in laundry and dish-washing products, anti-microbial, irritant if heated to combustion, apoptotic, pain reliever and
anti-inflammatory, in Lemon myrtle, principle constituent of lemongrass oil and oil of Litsea cubeba, also in African Tree basil, apricot,
lemon, orange, lemon balm
Citral has two terpenoid double bond isomers:
Geranial, Citral A, Citral E-isomer of citral, geranialdehyde, C10H16O, strong citrus lemon odour.
Neral, Citral B, cis-citral, lemonal, neroli aldehyde, Citral Z-isomer of citral, monoterpenoid, C10H16O, sweeter lemon odour, in
carrot
Lemon grass (Cymbopogon citratus), essential oil, citral terpenes, C51H84O5, used as a pesticide or preservative and may possibly
antifungal.

Citronellal
Citronellal, C10H18O, monoterpenoid, rhodinal, in Citrus depressa Taiwan mandarin, Melissa officinalis lemon balm,
85% of oil of Lemon-scented gum.

Citronellol
Citronellol, C10H20O, acyclic monoterpenoid, in citronella oils, Lemon grass, oils of rose, Pelargonium geraniums, in
Melissa officinalis, lemon balm.

Crocetin
Crocetin, C20H24O4, carotenoid pigment, (apocarotenoid), Trans-Crocetin, Natural Yellow-6, croceic acid.

Crocin
Crocin, C44H64O24, carotenoid pigment, alpha-crocin, Gardenia Yellow, crocin digentiobiose ester, water-soluble (apocarotenoid),
diterpene, gentiobiose diester of crocetin, from deep red forms orange solution, antioxidant, possibly anticancer, in Gardenia | Saffron.

Cuminaldehyde
Cuminaldehyde, C10H12O, 4-isopropylbenzaldehyde, cuminal, flavouring agent, suppresses melanin formation in melanoma cells,
in Cumin seed oil, possibly antidiabetic.

Curcumene
Curcumene, C15H22, sesquiterpene, alpha-curcumene, Curcuma xanthorrhiza, Javanese tumeric, wild tomato Lycopersicon hirsutum,
insecticide, insect repellent in tumeric, bright yellow.

Cymene
Cymene, C10H14, monoterpene-relative hydrocarbon, p-cymene, p-isopropyltoluene, p-cymol, cuminal, alkylbenzene, colourless liquid,
pleasant odour, floats on water, in oil of | Cumin | Thyme |.

Cyperene
Cyperene, C15H24, sesquiterpene, alpha-cyperene in nutgrass | burdock |.

Deoxylactucin
Deoxylactucin, C15H16O4, sesquiterpene lactone, 8-deoxylactucin, bitter taste, in common chicory roots and leaves, prickly lettuce.

Dehydroleucodine
Dehydroleucodine, C15H16O3, in Artemisia douglasiana.

Elemene
Elemene, C15H24, sesquiterpene (four isomers, alpha-, beta-, gamma-, delta-), floral aroma, possibly anticancerous.

Epomediol
Epomediol, C10H18O3, terpenoid, "Clesidren", used to treat itching, liver disorders, in Fennel.

Farnesene
Farnesene, C15H24, sesquiterpene (six isomers), acylic sesquiterpene, alpha-farnesene, flavour and fragrance agent, green apple
odour, oxidized to cause fruit skin scald, in oil or perilla, anti-viral, Perilla frutescens, gardenia aroma, pheromone to deter aphisds
Isomers occur in apple, orange, grapefruit, mandarin and lime peel, grape, pear ginger, nutmeg, basil.
Alpha- and beta-farnesene, in citronella oil, from Cymbopogon species.
Alpha-farnesene in coating of apple and pears, used as flavouring ingredient
Trans-beta-farnese is a hydrocarbon lipid molecule.

Farnesol
Farnesol, C15H26O, sesquiterpene, acyclic sesquiterpene alcohol, a farnesan
Colourless liquid, insoluble in water, miscible with oils, extracted from the oils of plants, flavouring, miticide.
In many essential oils, citronella, neroli, cyclamen, tuberose, bitter orange, ginger, jasmine, hops, beets, juniper, citronella, lemon grass,
tuberose, rose, musk, balsam of Peru, tolu balsam
In apricot, orange peel, grapefruit juice, cloves, ginger, thyme, basil, papaya, anise seed
In sweet acacia (needle bush), flowers used for floral essence perfumes.
Farnesol is a colourless liquid extracted from oils of plants such as citronella neroli, and tuberose and is then used in perfumery.
Farnesol, hydrophobic, enhances perfumes, in citronella, chamomile oil, oil of neroli petate, cyclamen, lemon grass, tuberose, rose,
musk, and balsam, frankincense, biofuel.

Fenchol
Fenchol, C10H18O, terpene, isomer of Borneol, used in perfumes, in Basil.

Fenchone
Fenchone, C10H16O, monoterpene ketone, colourless oily liquid, in the alcoholic drink absinthe, bitter taste of wild fennel, in oil of
Fennel.

Flavoxanthin
Flavoxanthin, C40H56O3, carotenoid pigment, golden-yellow, Food additive E161a (Banned some countries)
antioxidant, brown-olive xanthophyll, pigment, in brown algae, ester, health food, anti-cancer, antioxidant, anti-obesity, anti-inflammatory
The accessory pigment fucoxanthin is the brown pigment in brown algae and diatoms.

Forskolin
Forskolin, C22H34O7, diterpene, labdane diterpene, anti-hypertensive, in Coleus forskolin.

Gammacerane, C30H52, triterpenoid
Gammacerane has frequently been associated with hypersaline lacustrine environments.
Gammacerane structures were shown to be reliable geochemical indicators for water column stratification in marine deposits.
Gammacerane is one of several diagnostic biomarkers useful in oil spill analysis.
It is found in oils in southern Sicily.
Germacrene
Germacrene, C15H24, sesquiterpene, five isomers Germacrene A to E
Germacrene D is a constituent of essential oils, e.g. "Bee Balm" and "Golden Rod", anti-microbial, insecticidal
In marigolds, marjoram, oregano, juniper, frankincense, limoncello, red deadnettle (Lamium purpureum), lemon liqueur from lemon zest.
Germacrene B, C15H24, in essential oil of Purple deadnettle
Globulol
Gossypol, sesquiterpene dimer, from 2 cadinene units, in cotton, 2 isomers.

Geranic acid
Geranic acid, C10H16O2, monoterpene, decaprenoid acid, pheromone, isomer of Nerolic acid, in | Cardamom | Lemon grass |
Pettitgrain.

Geraniol
Geraniol, C10H18O, monoterpenoid, isomer of nerol, also as esters in rose oil (rose-like odour), palmarosa oil (best source),
citronella oil, geranium oil, lemon, lemongrass, lavender, almond, esters used in perfumes, flavours in peach, raspberry, grapefruit, red
apple, plum, lime, orange, lemon, watermelon, pineapple, blueberry.

Geranyl acetate
Geranyl acetate, C12H20O2, monoterpene, ester (geraniol + acetic acid), colourless liquid, mixed floral fruity rose or lavender aroma,
in many essential oils, used in many perfumes.

Ginkgolides
Ginkgolides, Ginkgo biloba, leaves
Gingolide A, C20H24O9, antioxidant
Gingolide B, C20H24O10, treat gardivascular diseases, possibly anti-cancer, neuroprotective
Gibberellin
Lupulin A
Pachydictol A
Retinoid
Taxodone.

Globulol
Globulol, C15H26O, floral rose odour, in perfumes.

Gossypol phenol
Gossypol phenol, C30H30O8, terpenoid alkaloid, inhibits some dehydrogenase enzymes, in cotton plant Gossypium, yellow pigment,
former contraceptive, but causes low blood potassium.

Grapefruit mercaptan
Grapefruit mercaptan, C10H18S, monoterpenoid, thioterpineol, causes grapefruit odour, but decomposes to a bad smell.

Guaiazulene
Guaiazulene, C15H18, sesquiterpene, azulon, bicyclic sesquiterpene, derivative of dark blue azulene C10H8, used in cosmetics, in
corals, anti-inflammatory, from Chamomile oil.

Hederagenin, C30H48O4, hederagenin, caulosapogenin, hederagenol, hederagenic acid
primary triterpenoid, triterpene saponin, in Caulophyllum robustum, Chenopodium quinoa, Hedera helix (common ivy)
See diagram: Hederagenin

Helenalin
Helenalin, C15H18O4, sesquiterpene lactone, anti-inflammatory, anti-cancer, antibacterial,
anti-protozoa, first isolated from Arnica species, in wolfsbane and aster, traditional medicine using alcoholic preparations from
Arnica montana and Arnica chamissonis flowers applied externally to treat hematomas, contusions, sprains, rheumatic diseases,
and skin inflammation, highly toxic, skin irritation.
, Mexicanin 1, C15H18O4, similar lactone, active against Trypanosoma cruzi.

Hinokitiol, beta-thujaplicin
Hinokitiol, C10H12O2, monoterpenoid, in Juniperus communis, in Juniperus cedrus, Thujopsis dolabrata, Thuja plicata, used to treat Chlamydia infections.
antibacterial, antiseptic, used in hair tonics and toothpaste. See diagram: Hinokitiol

Humulene
Humulene, C15H24, sesquiterpene, alpha caryophyllene, monocyclic sesquiterpene, in essential oils, | Hops.
See diagram: Humulene

Hydroxygeraniol
Hydroxygeraniol, C10H18O2, monoterpene, 8-Hydroxygeraniol, from monoterpenoid alcohol geraniol, C10H18O.

Incarvillateine
Incarvillateine, C42H58N2O8, monoterpene alkaloid, in Incarvillia sinensis.

Isovaleric acid
Isovaleric acid, C5H10O2, 3-methylbutanoic acid, fatty acid, in Valerian, (Valeriana officinalis), Caprifoliaceae.
Isovaleric acid has sweaty smell, underarm smell, foot smell, bad smell in wine to be reduced with sulfur dioxide
Isovaleric acid esters have pleasant smells, used in perfumes.

Jasmolone
Jasmolone, C11H16O2, "irregular monoterpene" (two isoprene units), secondary alcohol, acetic acid lavandulyl ester, colourless clear oily liquids, insecticide
perfuming agent, in | Lavender oil | Pyrethrum |.

Juvabione
Juvabione, C16H26O3, methyl ester, paper factor, in wood of Abies, balsam fir, insect hormone analogue.

Lactucin
Lactucin, C15H16O5, sesquiterpene lactone, white crystalline solid, bitter taste, in lactucarium latex (lettuce opium), milky fluid
secreted from wild lettuce, sedative, analgesic, euphoriant, antimalarial, acetylcholinase inhibitor, also in dandelion root.
8-Deoxylactucin, C15H16O4.

Lactucopicrin
Lactucopicrin, C23H22O7 (intybin), sesquiterpene lactone,
white crystalline solid, bitter taste, sedative, analgesic, euphoriant,
antimalarial, acetylcholinase inhibitor, in wild lettuce, common chicory, dandelion, garden lettuce, prickly lettuce.

Laurene
Laurene, C15H20, Laurencia glandulifera.

Lavandulol
Lavandulol, C10H18O, monoterpenoid alcohol, lavender oil, weak floral, herb-like odour with lemon-like citrus fruity nuance, insect
pheromone, in Lavender oil.

Lavandulyl acetate
Lavandulyl acetate, C12H20O2, ester of lavandulol, in lavender oil.

Limonene
Limonene, C10H16, monocyclic monoterpene, d-limonene, dipentene, racemic limonene, d-limonene, Toxic if ingested, Chinese
medicinal herb, used in synthesis of carvone, dissolves polystyrene, insect repellent, citrus fruits aroma
Limonene oil, basil, celery, citrus, cherry, dill, garlic, ginger, maize, rosemary, spearmint
Lemon juice, lemon oil, limonene
Li
monene is prepared by steam distillation of orange peel, then use cyclohexane to extract limonene.

Linalool
Linalool, C10H18O (CH3)2C=CH(CH2)2C(CH3)(OH)CH=CH2
acyclic monoterpene alcohol, two sterioisomers: R-linalool (licareol) and S-linalool (coriandrol).
Linalool has sweet floral spicy odour like Lily-of-the-valley, anti-inflammatory, analgesic, sedative, flavouring agent.
It is a major component of the aroma of 200 species, mainly Lamiaceae, Lauraceae and Rutaceae (citrus fruits), also birch trees
and fruits, e.g. guava, peach, plum, pineapple, passionfruit, tomato and allspice.
Linalool is a major constituent of 200 essential oils, including of coriander, palmarosa, also sweet orange flowers, lavender,
laurel, sweet basil, Indian bay leaf, Cannabis, goldenrod, mugwort, | Hops.
Linalool is used in perfumed hygiene products, insecticides, mosquito repellents.
See diagram: Linalool

Linalyl acetate
Linalyl acetate, ester (S)-linalyl acetate, C12H20O2, CH3COOC10H17, acetate ester of linalool, flowery fruit odour, plant metabolite,
mildly toxic, toxic to fish, in Bergamot, in Lavender oil.
: Linalyl acetate.

Longifolene
Longifolene, C15H24, sesquiterpene, tricyclic sesquiterpene, in Pinus roxberghii, lapsang souchong tea, pine resins.

Lupeol
Lupeol, C30H50O, in | Mango | Dandelion |.

Lutein
Lutein, C40H56O2, carotenoid pigment, an oxycarotenoid, xanthophyll pigment (ε-carotene, α-carotine-3, 3'diol), (an alcohol),
insoluble orange-red powder.
E161b Lutein, C40H56O2 (a xanthophyll pigment) (in egg yolk, green leaves, marigold flowers) (colour: yellow to red)
In spinach, kale, egg yolk, green leaves, marigold flowers, corn meal, many fruits and vegetables, human plasma.
Lutein is in the macula lutea, the oval shaped yellow spot near the centre of the retina, so reduces risk of macular degeneration to
improve visual function.
Lutein is an antioxidant that may help pregnant and lactating women and prevent atherosclerosis and damage from ultraviolet rays, but
consuming too much lutein causes carotenemia, orange skin.
Filters blue wavelengths of light from the visible-light spectrum by as much as 90%.

Lycopene
Lycopene, C40H56, carotenoid pigment, bioflavonoid carotene, carotenoid
E160d Lycopene, Food additive
Lycopene is a bright red carotene and carotenoid pigment, in ripe tomato, red fruits, carrot, bell pepper, watermelons, papaya,
asparagus, parsley
Lycopene, 90%, from tomato, ψ, ψ-Carotene, "Octamethyl-dotriaconta-tridecaene".
Lycopene is a, antioxidant micronutrient associated with decreased risk for prostate cancer, lung cancer, and cardiovascular disease.
It inhibits cholesterol synthesis and enhances low-density lipoprotein, (LSL), degradation.
Lycopene is supposed to be twice as powerful as beta carotene at neutralizing free radicals.
In older men, lycopene serum values decreases as the risk of prostate cancer increases.
In human blood serum, lycopene is the dominant carotenoid, about 50 %t of all carotenoids in the serum.

Lycopersene
Lycopersene, C40H66, carotenoid, ψ, ψ-Carotene, intermediate in carotene biosynthesis.

Matricarin
Matricarin, C17H22O5, sesquiterpenoid lactone, anti-inflammatory, antispasmotic, in popular herbal teas, in dried flower heads of
| German chamomile | Roman chamomile | Tilesius' wormwood |.

Menthol
Menthol, C10H20O, cyclic monoterpene, peppermint odour, : 16.3.6.7.
Menthol, C10H19OH, terpenoid alcohol, pleasant cooling odour and taste, rubifacient, decongestant, perfume, occurs in
Peppermint (Mentha X piperita), Lamiaceae, and in wild mint (Mentha arvensis).
Menthol binds to receptors on temperature-sensin nerve cells to give cooling sensation.
In peppermint leaves, the concentration of menthol increase with age, and menthol breaks down with heating so peppermint leaf is not
usually cooked.
Menthol, hexahydrothymol, Monoterpenes, C10 (2 isoprene units), C10H16: 16.3.5.1.1
Peppermint camphor (a methyl cyclohexanol) (mint flavour, peppermint flavour), eight sterioisomers
Menthol, mint camphor, rubifacient, white crystalline organic compound resembling camphor, extracted from oil of peppermint.
This compound is solid at room temperature and melts at about 37oC.
Natural menthol (-)-menthol, is an isomer with (1R, 2S, 5R) configuration, (1R, 2S, 5R)-2-Isopropyl-5-methylcyclohexane
Menthol is used in perfumes, menthol cigarettes, mild topical anaesthetic, and as a mint flavouring.
Menthol is antipruritic, reduces itching, so is used for relief of minor sore throat and mouth irritation.
The pure solution may damage eyes and sensitize skin, but < 10 mg in throat medicine lozenges is harmless.

Menthone
Menthone, C10H18O, monoterpene ketone, peppermint odour, in wild mint.

Menthoxypropanediol
Menthoxypropanediol, C13H26O3, synthetic derivative of menthol, in Vaseline.

Menthyl acetate
Menthyl acetate, C12H22O, in Peppermint.

Menthylisoborneol
Menthylisoborneol, 2-Menthylisoborneol, bad odour at very low concentration, affects drinking water, corky taste of wine.

Mercaptomenthone
Mercaptomenthone, 8-Mercaptomenthone, C10H18OS.

Methofuran
Methofuran, C10H14O, benzofuran, methane-3-8-diol, para-methan-3-8-diol, menthoglycol, in insecticide repellents, highly toxic,
in | Pennyroyal | Peppermint oil |.

Myrcene
Myrcene, C10H16, acyclic monoterpene, colourless-yellow, oily liquid, pleasant earthy clove-like odour, insoluble in water, most
abundant and possibly more than half terpenes in Cannabis, changes cell membranes for more brain absorption of cannabinoids, so
Cannabis smokers would first eat ripe mango, analgesic, antibacterial, anti-diabetic, anti-inflammatory, anti-mutagenic, antispasmotic,
helps sleep, tranquillizer, in Allspice | Basil | Bay tree | Cannabis | Hops | Mango | Myrcia sphaerocarpa | Parsley | Verbena |
Wild thyme | Ylang ylang |.

Myrcenol
Myrcenol, C10H18O, in Lavender oil, | Hops.

Myrtenal
Myrtenal, C10H14O, in cumin seed, juniper berry, pepper, peppermint, scotch spearmint.

Neoxanthin
Neoxanthin, C40H56O4, carotenoid pigment, green, in apple, paprika, lucerne, Valencia orange, spinach leaf, tomato and green
vegetables, and in Arabidopsis.

Nerol
Nerol, C10H18O, sweet rose odour, bitter flavour, used in perfumes
in | Lemongrass | Hops |.

Nerolic acid
Nerolic acid, C10H16O2, in honeybees.

Nerolidol
Nerolidol, C15H26O, sesquiterpene, acyclic sesquiterpene, a farnesan, peruvidol, cis and trans isomers, in neroli, ginger, jasmine,
lavender, tea tree and lemon grass,
Cannibis sativa, oleoresin, fresh bark smell, flavouring agent, woody aroma, in perfumes.

Neurosporene
Neurosporene, C40H58, carotene, carotenoid pigment.

Nomilin
Nomilin, C28H34O9, sesquiterpene lactone, bitter-tasting, in grapefruit.

Ocimene
Ocimene, C10H16, acyclic monoterpene, many isomers, e.g. beta-ocimene, flavour and fragrance agent, in Basil.

Orientin
Orientin, C21H20O11, flavone, lutexin, luteolin-6-C-glucoside, in bamboo leaves.

Parthenolide
Parthenolide, C15H20O3, sesquiterpenoid lactone, germacranolide, insoluble, non-steroidal anti-inflammatory, antipyretic, febrifuge,
inhibits release of seratonin from blood platelets, used to treat migraine headaches, possibly anticancer, in flowers, fruit, leaves of
| Feverfew | Laurel-leaved magnolia |.

Patachoulol
Patachoulol, C15H26O, sesquiterpene, tricyclic sesquiterpene alcohol, in Patchouli (Pogostemon cablin)

Peppermint oil
Peppermint oil
, terpene, Mentha piperita oil, C62H108O7, essential oil extracted from the leaves of Mentha x piperita, used for
aromatic properties, flavouring, treat disorders of digestive and respiratory system, pain.

Peridinin
Peridinin, C39H50O7, carotenoid pigment, light sensitive, associated with chlorophyll.

Perilla ketone
Perilla ketone, C10H14O2, lung toxin affecting cattle and horses, in Perilla species

Perillaldehyde
Perillaldehyde, C10H14O, sushi flavour, terpene aroma, perilla sugar, in Perilla species.

Perillartine
Perillartine, C10H15NO, perillartin, perilla sugar, X 2000 as sweet as sucrose, used in chewing gum, in Perilla frutescens.

Perillene
Perillene, C10H14O, may be anti-inflammatory, in Perilla frutescens.

Perillyl alcohol
Perillyl alcohol, monoterpene alcohol, woody odour, in essential oils of lavender, bergamot caraway, citrus oils, mints, anticancer

Petasin
Petasin, C20H28O3, sesquiterpene, ester of petasol (sencathenone), C15H22O2, and angelic acid, C5H8O2, in Butterbur, may be
anti-inflammatory.

Phellandrene, alpha-Phellandrene, Menthadiene
Phellandrene, C10H16, monocyclic monoterpene, fragrance and flavouring agent with peppermint / citrus taste, in allspice.
Cyclic monoterpene double bond isomers, having a similar molecular structure and similar chemical properties, are used in fragrances :
alpha-Phellandrene, α-phellandrene in Eucalyptus radiata
beta-phellandrene, β-phellandrene in oil of Canada balsam | Fennel | Perilla frutescens.
See diagram: Phellandrene

Phytoene
Phytoene, C40H64, carotene, carotenoid precursor, colourless, in most fruit and vegetables, tomato, carrot, oranges, absorb light in
the UV range, may protect human skin, antioxidant, anti-inflammatory (Phytoene/ phytofluene are the first step in synthesis of all
carotenoids in plants: phytoene --> neurosporene --> lycopene).

Phytofluene
Phytofluene, C40H62, carotene, carotenoid precursor, colourless, in most fruit and vegetables, orange colour of tomato, carrot,
oranges, absorb light in the UV range, may protect human skin, antioxidant, anti-inflammatory (phytoene --> phytofluene).

Picrotoxins
Picrotoxins
, C30H34O13.

Pinene
Pinene, C10H16, bicyclic monoterpene, alkene, reactive four-member ring, pine needles aroma, in Canarium species, Burseraceae.
Pinene is the terpene in natural turpentine from conifers and in essential oil of Rosemary.
α-Pinene, C10H16, clear colourless liquid, turpentine odour, less dense than water, insoluble in water, vapours heavier than air, used as
solvent, in Rosemary | Savory | Pinus | main component of Gum turpentine.
A terpenoid, called a crystalline hydrate, C6H10(CH3)3(OH)2, is formed from acidification of α-Pinene
β-Pinene, C10H16, much released in pine forests, in Pinus | Cumin | Hops | Cannabis | Horsewood.
Enantiomer alpha-pinene more common in European pines, Enantiomers beta-pinene more common in North America pines.

Pinocamphone
Pinocamphone, C10H16O, monoterpene ketone, dark yellow liquid, aromatic, pleasant odour, in the alcoholic drink absinthe, may
lead to disorders of the nervous system, in Hyssop.

Piperitone
Piperitone, C10H16O, monoterpene ketone, D-piperitone in Mint, and L-piperitone in Picea sitchensis.

Prenol
Prenol, C5H10O, fruit-like odour in citrus, tomato, passionfruit, Prenol hemiterpenoids, alcohols, carbon skeleton is one or more
isoprene units.

Pulegone
Pulegone, C10H16O, monoterpene, natural pesticide,
in Schizonepeta tenuifalia | Catnip | Mentha piperita | Pennyroyal (Mentha pulegium), Lamiaceae.

Retene
Retene, C18H18, methyl isopropyl phenanthrene, polycyclic aromatic hydrocarbon, from degraded conifer diterpene.

Rhodinol
Rhodinol, C10H20O, monoterpene alcohol, floral fragrance, in citronella oil, in Lemongrass.

Rhodopin
Rhodopin, C40H58O, carotenoid pigment (an alcohol), phototrophic bacteria.

Rhodoxanthin
Rhodoxanthin, C40H50O2, retro-carotenoid pigment, purple, Food additive E161f, Rhodoxanthin, in Yew tree.

Rose oxide
Rose oxide, C10H18O, monoterpenoid, fragrance chemical, roses oil, lychee, Gewurztraminer wines.

Rubixanthin
Rubixanthin, C40H56O, xanthophyll pigment, red-orange, natural yellow 27, food colouring (Banned some countries), in | Roships |
Apricot |.

Sabinene
Sabinene, C10H16, bicyclic monoterpene, in | Horsewood | Pepper |.

Sabinene hydrate
Sabinene hydrate, C10H18O, 4-Thujanol.

Safranal
Safranal, C10H14O, 2, 3-dihydro-2, 2, 6-trimethylbenzaldehyde, bitter taste, hay-like fragrance, antioxidant, anticonvulsant,
antidepressant, in | Saffron | Tea plant | Cumin | Fig | Lemon |.

Selinene
Selinene, C15H24, sesquiterpene (group of 4 isomers) , alpha- and beta-Selinene, in celery seed oil.

Squalene
Squalene, C30H50, clear, slightly yellow liquid, faint odour, in liver oil of sharks in amaranth seed, rice bran, wheat germ olives, used
in cosmetics, precursor to sterol biosynthesis.

Staphyloxanthin
Staphyloxanthin, C51H78O8, carotenoid pigment, produced by Staphylococcus aureus ("golden staph")

Steviol
Steviol C20H30O3, from Stevia rebaudiana, artificial sweetener
Tanishone, Salvia miltiorrhiza, Lamiaceae
Taxadiene, taxol (in yew tree bark, anticancer)
Taxol
Trisporic acid (fungal hormones).

Terpinene
Terpinene, cyclic terpene, C10H16
alpha-terpinene, oil with lemon smell, cardamum, coriander, marjoram
beta-Terpinene, from oil of savin
gamma-Terpinene, coriander, cumin lemon, samphire.

Terpineol
Terpineol, C10H18O, α-terpineol, monoterpene alcohol, from pine oil, colourless solid, lilac floral odour, sweet lime taste, lilac floral
flavour, soluble in alcohol, heated emits acrid irritating fumes | in Cinnamon | cajuput oil | pine oil | petitgrain oil | alpha-, beta- and
gamma- isomers.
Terpene alcohol, three isomeric alcohols, C10H17OH, in essential oils, used as solvents in perfumes, soaps, and medicine.

Terpinoline
Terpinoline, C10H16, monocyclic monoterpene, terpinene, flavour and fragrance agent.

Terpinyl acetate
Terpinyl acetate, C12H20O2, oleoresin from pine oil.

Terpyridine
Terpyridine, C15H11N3, tridentate ligand.

Tetrahydrolinalool
Tetrahydrolinalool, C10H22O, monoterpene, 7-dimethyl-3-octanol, colourless liquid, flavouring ingredient, perfumes.

Thujene
Thujene, C10H16, bicyclic monoterpene, isomers: alpha-thujene, sabinene thujene, colourless to pale yellow clear liquid, woody,
spicy, pine-like odour and taste, in Quercus ilex, Fagaceae, Picea abies, Pinaceae, black pepper, carrot seed oil, tea tree oil.

Thujone
Thujone, C10H16O, bicyclic monoterpene ketone, menthol odour, in oil of wormwood, from (Artemisia absinthium), cedar leaves,
used in the alcoholic drink absinthe, colourless liquid, almost insoluble in water but soluble in alcohol
α-thujone (alpha-thujone), C10H16O | L-thujone, C10H16O | β-thujone (beta-thujone) C10H16O.
Thujone has two diastereomeric forms: (-)-alpha-thujone and (+)-beta-thujone and there are their enantiomeric forms (+)-alpha-thujone
and (-)-beta-thujone.
Costmary oil, bible leaf oil, former medicine, contains about 12% beta-thujone.

Thujopsene
Thujopsene, C15H24, Turpentine --> rosin, in conifers.

Thymoquinone
Thymoquinone, C10H12O2, used to treat urinary tract infection, may be analgesic, anti-convulsant, anti-cancer, in | Nigella |
Wild bergamot |.

Verbenone
Verbenone, C10H14O, pleasant odour, in lemon verbena  (Aloysia citrodora).
See diagram: Verbenone

Violaxanthin
Violaxanthin, C40H56O4, carotenoid pigment, zeaxanthin diepoxide, orange crystals, Food additive E160e, in Heartsease, wild pansy.
See diagram: Violaxanthin

Vulgarin
Vulgarin, C15H20O4, sesquiterpene, tauremizin, Judaicin, Barellin, in Artemisia species.

Wine lactone
Wine lactone, C10H14O2, pleasant odour, in citrus juices, wine, clementine peel oil.
See diagram: Winelactone

Zeaxanthin
Zeaxanthin, C40H56O2, carotenoid pigment, the most common xanthophyll pigment (ester of an alcohol), gives colour to peppers,
paprika, saffron, wolfberry (beta, beta-carotene-3-3'-diol), ester, furanoxide, yellow xanthophyll carotenoid pigment, common
carotenoid alcohol, causes yellow colour of maize (corn flakes) (Zea mays), peppers, paprika, saffron, wolfberries,
In dark green, leafy vegetables such as spinach, collard greens, kale, mustard greens, and turnip greens.
In bell peppers, saffron, spinach, kale, broccoli, maize, wolfberry, many fruits.
Carotenoid pigment that contributes to the color of paprika.
Zeaxanthin accumulates within the eye retina, may decrease the incidence of macular degeneration.
Zeaxanthin and lutein, C40H56O2, are the two carotenoid pigments contained within the retina of the eye, in the macula lutea.
They are both powerful antioxidants, absorb blue light and may protect the retina, prevent macular degeneration and cataracts.
Chicken egg yolks contain about 290 micrograms of lutein per yolk, and 210 micrograms of zeaxanthin per yolk.
Name from Zea Mays, maize (corn flakes).
Zeaxanthin breaks down to form | Picrocrocin | and Safranal |.
See diagram: Zeaxanthin

Zingiberine
Zingiberine, C15H24, sesquiterpene, alpha-zingiberine, monocyclic sesquiterpene in Zingiber officinale, up to 30% of oil of ginger (ginger oil).
See diagram: Zingiberine