School Science Lessons
Please send comments to: J.Elfick@uq.edu.au
Table of contents
See: OrganicChemistry, Biochemistry (Commercial)
188.8.131.52 Terpenes (C5H8)n
184.108.40.206a Terpenoids, isoprenoids (C5H8)n,
220.127.116.11b Terpinenes (cyclic terpenes) (C10H16)
18.104.22.168 Terpenes (C5H8)n
22.214.171.124 Terpenes (C5H8)n
16.3.5.02 Isoprene units (C5H8), (CH2=C(CH3)CH=CH2)
126.96.36.199.1 Hemiterpenes (C5H8), (one isoprene unit)
188.8.131.52.2 Monoterpenes (C10H16), (two isoprene units)
184.108.40.206.3 Sesquiterpenes (C15H24), (three isoprene units)
220.127.116.11.4 Diterpenes (C20H32), (four isoprene units)
18.104.22.168.5 Sesterterpenes (C25H40), (five isoprene units)
22.214.171.124.6 Triterpenes (C30H48), (six isoprene units)
126.96.36.199.8 Tetraterpenes (C40H64), (eight isoprene units)
188.8.131.52.9 Polyterpenes (C5H8)n, (many isoprene units)
| Alvonal MR, Cymarine | Digitoxin | Digoxin
| Ouabain | Strophanthin |
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)
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
See diagram: Iridoid molecules
Monoterpenoid lactones, in many dicotyledons, bitter tasting, large concentrations toxic, in folk medicines
isoprenoids (C5H8)n, modified terpenes
184.108.40.206a Terpenoids, isoprenoids,
(C5H8)n, modified terpenes
220.127.116.11.1a Hemiterpenoids (C5H8)
18.104.22.168.2 Monoterpenoids (C10H16)
22.214.171.124.3a Sesquiterpenoids (C15H24)
126.96.36.199.3b Sesquiterpenoid lactones (C22H30O7)
188.8.131.52.4a Diterpenoids (C20H32)
184.108.40.206.5a Sesterterpenoids (C25H40)
220.127.116.11.6a Triterpenoids (C30H48)
--> natural steroids
18.104.22.168.8a Tetraterpenoids, carotenoids (C40H64)
Two classes of Tetraterpenoids:
22.214.171.124.0 Carotenes (C40Hx)
126.96.36.199.0 Xanthophylls (C40H56On)
188.8.131.52b Terpinenes (cyclic
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,
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.
(one isoprene unit) (C5H8)
is the only hemiterpene.
(two isoprene units) (C10H16) and Monoterpenoids
Camphor, DL-Camphor, C10H16O: 184.108.40.206
monoterpenoid, Two isomers: Neral, C10H16O, Citral
Chrysanthemic acid, C10H16O2
Geranic acid, C10H16O2
, monoterpenoid alcohol
Geranyl acetate, C12H20O2
Grapefruit mercaptan, C10H18S,
Lavandulol, C10H18O, monoterpenoid
Linalyl acetate, C12H20O2
Menthyl acetate, C12H22O2
Nerolic acid, C10H16O2
Perilla ketone, C10H14O2
Perillyl alcohol, C10H16O
Rose oxide, C10H18O,
Sabinene hydrate, C10H18O
Wine lactone, C10H14O2
Iridoids are cyclic monoterpenoids having the iridane skeleton (1-isopropyl-2,
Iridoid monoterpenoid, C16H22O10
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
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
Sesquiterpenes are formed from three isoprene units.
They may be acyclic, mono-, di-, or tricyclic; synthesized from farnesyl
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
Jasmalone, 2-hexylidenecyclopentanone, C11H18O
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,
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).
(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
Germacranolides, group of sesquiterpenoid lactones
Germacranolide, C15H22O4, in bigroot Geranium.
Eudesmanolides, group of sesquiterpenoid lactones
Eudesmanolide, in Japanese bigleaf
Paludolactone, in Wedelia paludosa, creeping ox-eye.
Guaiaolides, group of sesquiterpenoid lactones
15-nor-guaianolide, C14H18O4, azulene
sesquiterpenoid lactone, in Guaiac wood.
(four isoprene units), C20H32
In perfumes and resins, pine turpentine, distilled essential oil,
Abietic acid, Pinus, most abundant compound in rosin
220.127.116.11.4a Diterpenoids, C20
(five isoprene units)
Sesterterpenes, C25, in insect waxes, fungi products, phytotoxins, geranyl,
farnesol, ceroplastol, insect gascardic acid
Phyllofenone, in South Seas sponge.
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.
18.104.22.168.6a Triterpenoids, C30, antioxidant properties, prevent lipid peroxidation and suppress superoxide anion generation.
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.
See diagram: Oleanolic acid.
C30, any terpenoid derived from triterpene
Betulinic acid, C30H48O3
Gammacerane, C30H52, triterpenoid
Oleanolic acid, C30H48O3
22.214.171.124.6b 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
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
Digitogenin (C27H44O5), sapogenin, hydroxy
Diosgenin (C27H42O3), steroid sapogenin,
in Costus speciosis, Dioscorea species, wild yam
Tiggenin, in Chlorophytum borivilianum
Yamogenin (C27H42O3), sapogenin, in Trigonella
126.96.36.199.6b Tests for
Add ground plant material to test-tube of water, heat to boiling, add stopper
and shake the test-tube.
Note presence of stable froth.
C40 (eight isoprene units)
Tetraterpenes, C40 (eight isoprene units), C40H56,
carotenoid pigments, e.g. alpha-carotene, C40H56,
alpha-carotene and beta-carotene, their derivatives, tetraterpenoids, are
terpenoids of 8 isoprene units, 40 carbon atoms in the skeleton.
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
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
Carotenoids are divided into carotenes and xanthophylls.
188.8.131.52.0 Carotenes, C40Hx
184.108.40.206.0 Xanthophylls, C40H56On.
(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.
Rubber, latex (C5H8)n, [n = 4, 0005, 000], trans-1.4-polyisoprene,
cis double bonds, from latex of: (Hevea brasiliensis), and (Ficus
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.
Chicle, polyterpene, from the
sapodilla tree (Manilkara zapota), used for chewing gums.
Norisoprenoids, C13, Vitis vinifera.
220.127.116.11.0 Carotenes (C40Hx)
Boiling, test the cooking water of boiled vegetables: 19.3.3 (See 1. and 6.)
Carotenoids, Tetraterpenoids: 18.104.22.168.8a
Cells, plant cells, Elodeas: 9.9.0
Chromatography of chlorophyll pigments: 6.5.5
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.
Fucoxanthin, Lycopene, Retinoic acid,
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
E160e, Beta-apo-8' carotenal,
E160f, Ethyl ester of beta-apo-8
Carotenes are hydrocarbon carotenoids, a subclass of tetraterpenes and C5n
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
β-Carotene, Type II, synthetic, 95% (HPLC), crystalline, β, β-Carotene,
Provitamin A, C40H56.
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.
are hydrocarbons + oxygen, and are usually yellow pigments
Xanthophylls, contain oxygen, usually yellow pigments, in the leaves of
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
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
Xanthophyll from marigold
Apocarotenoids (C<40), Derived from carotenoids by oxidative cleavage
22.214.171.124 Abscisic acid, C15H20O4,
isoprenoid plant hormone, guard cells
Isovaleric acid, C5H10O2.
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.
126.96.36.199 Abscisic acid, C15H20O4,
Ambrein, C30H52O, a triterpene alcohol, is the main
constituent of ambergris found in the sperm whales or floating on the sea
whale barf (vomit), whale spit.
It is supposed to protect the intestines of whales from the sharp beaks
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, C20H30O5, labdane diterpenoid, produced by Andrographis paniculata
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.
Andrographolide occurs in King of bitters.
See diagram: Andrographolide
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, C40H56O3, , xanthophyll
carotenoid, oil-soluble alcohol, bright yellow accessory pigment, in Capsicum.
See diagram: Antheraxanthin
Artemisinin, C15H22O5, sesquiterpenoid
lactone, artemisene, qinghaosu, ancient Chinese herbal medicine, used to treat
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, 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, 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).
Azadirachtin, C34H44O16, triterpenoid, yellow-green powder, strong garlic/sulphur odour,
tetranortriterpenoid, natural pesticide, in Neem tree,
Azadirachta indica, Meliaceae.
See diagram: Azadirachtin
Azafrin, C27H38O4, escobedin, sesterterpenoid,
in Azafranillo, Escobedia scabrifolia, Scrophulariaceae.
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
188.8.131.52 Furanocoumarin, furocoumarin.
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, C15H26O, sesquiterpene (bisabolane), monocyclic sesquiterpene alcohol
essential oils from leaves alpha-bisabolol, from leaves of Hymenocrater yazdianus
and in German chamomile.
See diagram: Bisabolol
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, C10H18, terpene, camphane, bornylane, crystalline,
saturated, "parent compound" of borneol and camphor, in
Camphor laurel tree.
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, C15H18, sesquipertene derivative, cadalin,
polycyclic aromatic hydrocarbon, in essential oils many plants, e.g. Pinaceae.
Cadinene, C15H24, sesquiterpene, bicyclic sesquiterpene,
beta-cadinene, in Juniperus
Capsidiol in tobacco, chilli after infection.
Cafestol, C20H28O3, diterpene, in coffee
bean oil, anti-inflammatory, associated with some natural cell death, some
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:
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, 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
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, C40H56O3, keto-carotenoid
E160c: Capsanthin food additive, Paprika
Capsidiol, C15H24O2, bicyclic terpene,
occurs in tobacco Nicotiana tabacum, chili pepper Capsicum annuum,
forms in response to
Capsorubin, C40H56O4, keto-carotenoid
E160c: Capsorubin food additive, Paprika
extract, Capsanthin, red paprika pigment.
Carene, C10H16, bicyclic monoterpene, delta-3-carene,
sweet, pungent odour, alpha-carene flavouring ingredient, in allspice,
rosemary, Turpentine tree.
Citranaxanthin, C33H44O, carotenoid pigment, yellow
food dye (apocarotenoid from cleavage of carotenoid).
E161g: Citranaxanthin food additive.
Cryptoxanthin, C40H56O, carotenoid pigment, in yellow
maize, orange and red pumpkins and chillies
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 A and B, C32H50O8S from marine
Carvacrol, C10H14O, monoterpenoid phenol, cymophenol,
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, 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, C10H14O, monocyclic monoterpene, volatile
terpenoid ketone, colourless to slightly yellow liquid, prevents potatoes
mosquito repellent, very abundant in caraway seed, and in dill, spearmint, costmary, kuromoji and other oils, ancient Roman medicine
D-carvone [(R)-Carvone] has Caraway odour.
L-carvone [(R)-Carvone] has Spearmint odour.
Carvonic acid, C10H12O3, terpenoid from carvone.
See diagram: Carvone
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, C15H26O, sesquiterpene alcohol, essential oil
of conifers, cedarwood oil, in Cupressus and Juniperus.
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 |
Mugwort | Sneezewort |
Wormwood | Yarrow |
sesquiterpene lactone matricin, C17H22O5
--> azulene, C10H8 ---> chamazulene, C14H16.
See diagram: Chamazulene
Chrysanthemic acid, C10H16O2, causes skin
and eye irritation, related to pyrethrin insecticides in Chrysanthemum.
Chrysanthenone, C10H14O, terpene, 2-pinene-7-one,
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
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),
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,
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
Lemon grass (Cymbopogon citratus),
essential oil, citral terpenes, C51H84O5,
used as a pesticide or preservative and may possibly
Citronellal, C10H18O, monoterpenoid, rhodinal, in
Citrus depressa Taiwan mandarin, Melissa officinalis lemon
85% of oil of Lemon-scented
Citronellol, C10H20O, acyclic monoterpenoid, in citronella
oils, Lemon grass, oils of rose,
Pelargonium geraniums, in
Melissa officinalis, lemon balm.
Crocetin, C20H24O4, carotenoid pigment,
(apocarotenoid), Trans-Crocetin, Natural Yellow-6, croceic acid.
Crocin, C44H64O24, carotenoid pigment,
alpha-crocin, Gardenia Yellow, crocin digentiobiose ester, water-soluble
diterpene, gentiobiose diester of crocetin, from deep red forms orange solution,
antioxidant, possibly anticancer, in Gardenia | Saffron.
Cuminaldehyde, C10H12O, 4-isopropylbenzaldehyde,
cuminal, flavouring agent, suppresses melanin formation in melanoma cells,
in Cumin seed oil, possibly antidiabetic.
Curcumene, C15H22, sesquiterpene, alpha-curcumene,
Curcuma xanthorrhiza, Javanese tumeric, wild tomato Lycopersicon
insecticide, insect repellent in tumeric, bright yellow.
Cymene, C10H14, monoterpene-relative hydrocarbon,
p-cymene, p-isopropyltoluene, p-cymol, cuminal, alkylbenzene, colourless
pleasant odour, floats on water, in oil of | Cumin | Thyme |.
Cyperene, C15H24, sesquiterpene, alpha-cyperene in
nutgrass | burdock |.
Deoxylactucin, C15H16O4, sesquiterpene
lactone, 8-deoxylactucin, bitter taste, in common chicory roots and leaves,
Dehydroleucodine, C15H16O3, in Artemisia
Elemene, C15H24, sesquiterpene (four isomers, alpha-,
beta-, gamma-, delta-), floral aroma, possibly anticancerous.
Epomediol, C10H18O3, terpenoid, "Clesidren",
used to treat itching, liver disorders, in Fennel.
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, 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, C10H18O, terpene, isomer of Borneol, used in perfumes, in Basil.
Fenchone, C10H16O, monoterpene ketone, colourless
oily liquid, in the alcoholic drink absinthe, bitter taste of wild fennel,
in oil of
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
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, 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
Gossypol, sesquiterpene dimer, from 2 cadinene units, in cotton, 2 isomers.
Geranic acid, C10H16O2, monoterpene, decaprenoid
acid, pheromone, isomer of Nerolic acid,
in | Cardamom | Lemon grass |
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, C12H20O2, monoterpene,
ester (geraniol + acetic acid), colourless liquid, mixed floral fruity
rose or lavender aroma,
in many essential oils, used in many perfumes.
Ginkgolides, Ginkgo biloba, leaves
Gingolide A, C20H24O9, antioxidant
Gingolide B, C20H24O10, treat gardivascular
diseases, possibly anti-cancer, neuroprotective
Globulol, C15H26O, floral rose odour, in perfumes.
Gossypol phenol, C30H30O8, terpenoid alkaloid,
inhibits some dehydrogenase enzymes, in cotton plant Gossypium,
former contraceptive, but causes low blood potassium.
Grapefruit mercaptan, C10H18S, monoterpenoid, thioterpineol,
causes grapefruit odour, but decomposes to a bad smell.
Guaiazulene, C15H18, sesquiterpene, azulon, bicyclic
sesquiterpene, derivative of dark blue azulene C10H8,
used in cosmetics, in
corals, anti-inflammatory, from Chamomile
Hederagenin, C30H48O4, hederagenin, caulosapogenin, hederagenol, hederagenic acid
primary triterpenoid, triterpene saponin, in Caulophyllum robustum, Chenopodium quinoa, Hedera helix (common ivy)
See diagram: Hederagenin
See diagram: Hederagenin
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, 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, C15H24, sesquiterpene, alpha caryophyllene, monocyclic sesquiterpene, in essential oils, | Hops.
See diagram: Humulene
Hydroxygeraniol, C10H18O2, monoterpene,
8-Hydroxygeraniol, from monoterpenoid alcohol geraniol, C10H18O.
monoterpene alkaloid, in Incarvillia
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, C11H16O2, "irregular monoterpene"
(two isoprene units), secondary alcohol, acetic acid lavandulyl ester, colourless clear oily
perfuming agent, in | Lavender
oil | Pyrethrum |.
Juvabione, C16H26O3, methyl ester, paper
factor, in wood of Abies, balsam fir, insect hormone analogue.
Lactucin, C15H16O5, sesquiterpene lactone,
white crystalline solid, bitter taste, in lactucarium latex (lettuce opium),
secreted from wild lettuce, sedative, analgesic, euphoriant, antimalarial,
acetylcholinase inhibitor, also in dandelion root.
Lactucopicrin, C23H22O7 (intybin), sesquiterpene
white crystalline solid, bitter taste, sedative, analgesic, euphoriant,
antimalarial, acetylcholinase inhibitor, in wild lettuce, common chicory,
dandelion, garden lettuce, prickly lettuce.
Laurene, C15H20, Laurencia glandulifera.
Lavandulol, C10H18O, monoterpenoid alcohol, lavender
oil, weak floral, herb-like odour with lemon-like citrus fruity nuance,
pheromone, in Lavender oil.
Lavandulyl acetate, C12H20O2, ester of
lavandulol, in lavender oil.
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,
Lemon juice, lemon oil, limonene
monene is prepared by steam distillation of orange peel, then use
cyclohexane to extract limonene.
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, 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.
See diagram: Linalyl acetate.
Longifolene, C15H24, sesquiterpene, tricyclic sesquiterpene,
in Pinus roxberghii, lapsang souchong tea, pine resins.
Lupeol, C30H50O, in | Mango | Dandelion |.
Lutein, C40H56O2, carotenoid pigment,
an oxycarotenoid, xanthophyll pigment (ε-carotene, α-carotine-3, 3'diol),
insoluble orange-red powder.
E161b Lutein, C40H56O2 (a xanthophyll
pigment) (in egg yolk, green leaves, marigold flowers) (colour: yellow
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, C40H56, carotenoid pigment, bioflavonoid
E160d Lycopene, Food additive
Lycopene is a bright red carotene and carotenoid pigment, in ripe tomato,
red fruits, carrot, bell pepper, watermelons, papaya,
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,
Lycopene is supposed to be twice as powerful as beta carotene at neutralizing
In older men, lycopene serum values decreases as the risk of prostate cancer
In human blood serum, lycopene is the dominant carotenoid, about 50 %t of
all carotenoids in the serum.
Lycopersene, C40H66, carotenoid, ψ, ψ-Carotene, intermediate
in carotene biosynthesis.
Matricarin, C17H22O5, sesquiterpenoid
lactone, anti-inflammatory, antispasmotic, in popular herbal teas, in dried
flower heads of
| German chamomile | Roman chamomile | Tilesius' wormwood |.
Menthol, C10H20O, cyclic monoterpene, peppermint
odour, : 184.108.40.206.
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
In peppermint leaves, the concentration of menthol increase with age, and
menthol breaks down with heating so peppermint leaf is not
Menthol, hexahydrothymol, Monoterpenes, C10 (2 isoprene units), C10H16:
Peppermint camphor (a methyl cyclohexanol) (mint flavour, peppermint flavour),
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, C10H18O, monoterpene ketone, peppermint
odour, in wild mint.
Menthoxypropanediol, C13H26O3, synthetic
derivative of menthol, in Vaseline.
Menthyl acetate, C12H22O, in Peppermint.
Menthylisoborneol, 2-Menthylisoborneol, bad odour at very low concentration,
affects drinking water, corky taste of wine.
Mercaptomenthone, 8-Mercaptomenthone, C10H18OS.
Methofuran, C10H14O, benzofuran, methane-3-8-diol,
para-methan-3-8-diol, menthoglycol, in insecticide repellents, highly toxic,
in | Pennyroyal | Peppermint oil |.
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, C10H18O, in Lavender oil, | Hops.
Myrtenal, C10H14O, in cumin seed, juniper berry,
pepper, peppermint, scotch spearmint.
Neoxanthin, C40H56O4, carotenoid pigment,
green, in apple, paprika, lucerne, Valencia orange, spinach leaf, tomato
vegetables, and in Arabidopsis.
Nerol, C10H18O, sweet rose odour, bitter flavour,
used in perfumes
in | Lemongrass | Hops |.
Nerolic acid, C10H16O2, in honeybees.
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, C40H58, carotene, carotenoid pigment.
Nomilin, C28H34O9, sesquiterpene lactone,
bitter-tasting, in grapefruit.
Ocimene, C10H16, acyclic monoterpene, many isomers,
e.g. beta-ocimene, flavour and fragrance agent, in Basil.
Orientin, C21H20O11, flavone, lutexin,
luteolin-6-C-glucoside, in bamboo leaves.
Parthenolide, C15H20O3, sesquiterpenoid
lactone, germacranolide, insoluble, non-steroidal anti-inflammatory, antipyretic,
inhibits release of seratonin from blood platelets, used to treat migraine
headaches, possibly anticancer, in flowers, fruit, leaves of
| Feverfew | Laurel-leaved magnolia |.
Patachoulol, C15H26O, sesquiterpene, tricyclic sesquiterpene alcohol, in Patchouli (Pogostemon cablin)
Peppermint oil, terpene, Mentha piperita oil, C62H108O7,
essential oil extracted from the leaves of Mentha x piperita, used
aromatic properties, flavouring, treat disorders of digestive and respiratory
Peridinin, C39H50O7, carotenoid pigment,
light sensitive, associated with chlorophyll.
Perilla ketone, C10H14O2, lung toxin
affecting cattle and horses, in Perilla
Perillaldehyde, C10H14O, sushi flavour, terpene
aroma, perilla sugar, in Perilla
Perillartine, C10H15NO, perillartin, perilla sugar,
X 2000 as sweet as sucrose, used in chewing gum, in Perilla frutescens.
Perillene, C10H14O, may be anti-inflammatory, in
Perillyl alcohol, monoterpene alcohol, woody odour, in essential oils of
lavender, bergamot caraway, citrus oils, mints, anticancer
Petasin, C20H28O3, sesquiterpene, ester
of petasol (sencathenone), C15H22O2, and
angelic acid, C5H8O2, in Butterbur, may be
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, C40H64, carotene, carotenoid precursor,
colourless, in most fruit and vegetables, tomato, carrot, oranges, absorb
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, 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).
See diagram: Picrocrocin
Picrocrocin, C16H26O7, monoterpene glucoside (Saffron-bitter), an ester of crocetin (C20H24O4), precursor of | Safranal | in Gardenia |
| Saffron |.
Picrocrocin is a beta-D-glucoside derived from beta-cyclocitral (C10H16O), the precursor of safranal (C10H14O), the compound most responsible for the bitter taste of saffron.
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, 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, C10H16O, monoterpene ketone, D-piperitone
in Mint, and L-piperitone in Picea sitchensis.
Prenol, C5H10O, fruit-like odour in citrus, tomato,
passionfruit, Prenol hemiterpenoids, alcohols, carbon skeleton is one or
Pulegone, C10H16O, monoterpene, natural pesticide,
in Schizonepeta tenuifalia | Catnip
| Mentha piperita | Pennyroyal (Mentha pulegium), Lamiaceae.
Retene, C18H18, methyl isopropyl phenanthrene, polycyclic
aromatic hydrocarbon, from degraded conifer diterpene.
Rhodinol, C10H20O, monoterpene alcohol, floral fragrance,
in citronella oil, in Lemongrass.
Rhodopin, C40H58O, carotenoid pigment (an alcohol),
Rhodoxanthin, C40H50O2, retro-carotenoid
pigment, purple, Food additive E161f,
Rhodoxanthin, in Yew tree.
Rose oxide, C10H18O, monoterpenoid, fragrance chemical,
roses oil, lychee, Gewurztraminer wines.
Rubixanthin, C40H56O, xanthophyll pigment, red-orange,
natural yellow 27, food colouring (Banned some countries), in | Roships |
Sabinene, C10H16, bicyclic monoterpene, in | Horsewood | Pepper |.
Sabinene hydrate, C10H18O, 4-Thujanol.
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, C15H24, sesquiterpene (group of 4 isomers)
, alpha- and beta-Selinene, in celery seed oil.
Squalene, C30H50, clear, slightly yellow liquid,
faint odour, in liver oil of sharks in amaranth seed, rice bran, wheat germ
in cosmetics, precursor to sterol biosynthesis.
Staphyloxanthin, C51H78O8, carotenoid
pigment, produced by Staphylococcus aureus ("golden staph")
Steviol C20H30O3, from Stevia rebaudiana,
Tanishone, Salvia miltiorrhiza, Lamiaceae
Taxadiene, taxol (in yew tree bark, anticancer)
Trisporic acid (fungal hormones).
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, C10H18O, α-terpineol, monoterpene alcohol,
from pine oil, colourless solid, lilac floral odour, sweet lime taste,
flavour, soluble in alcohol, heated emits acrid irritating fumes | in Cinnamon | cajuput oil | pine oil | petitgrain oil | alpha-, beta-
Terpene alcohol, three isomeric alcohols, C10H17OH,
in essential oils, used as solvents in perfumes, soaps, and medicine.
Terpinoline, C10H16, monocyclic monoterpene, terpinene,
flavour and fragrance agent.
Terpinyl acetate, C12H20O2, oleoresin
from pine oil.
Terpyridine, C15H11N3, tridentate ligand.
Tetrahydrolinalool, C10H22O, monoterpene, 7-dimethyl-3-octanol,
colourless liquid, flavouring ingredient, perfumes.
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, 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
Costmary oil, bible leaf oil, former medicine, contains about 12% beta-thujone.
Thujopsene, C15H24, Turpentine --> rosin, in conifers.
Thymoquinone, C10H12O2, used to treat
urinary tract infection, may be analgesic, anti-convulsant, anti-cancer,
in | Nigella |
Wild bergamot |.
Verbenone, C10H14O, pleasant odour,
in lemon verbena (Aloysia citrodora).
See diagram: Verbenone
Violaxanthin, C40H56O4, carotenoid pigment,
zeaxanthin diepoxide, orange crystals, Food additive E160e, in Heartsease, wild pansy.
See diagram: Violaxanthin
Vulgarin, C15H20O4, sesquiterpene, tauremizin,
Judaicin, Barellin, in Artemisia species.
Wine lactone, C10H14O2, pleasant odour,
in citrus juices, wine, clementine peel oil.
See diagram: Winelactone
Zeaxanthin, C40H56O2, carotenoid pigment,
the most common xanthophyll pigment (ester of an alcohol), gives colour
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
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
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, C15H24, sesquiterpene, alpha-zingiberine,
monocyclic sesquiterpene in Zingiber
officinale, up to 30% of oil of ginger (ginger oil).
See diagram: Zingiberine