School Science Lessons
Topic 16c
2019-07-21
Please send comments to: J.Elfick@uq.edu.au
Topic 16c
Plant oils
See: Biochemistry (Commercial)
Table of contents
16.3.5.1a Aescin
16.3.5.1 Aesculin
16.3.2.0 Aldehydes
16.3.6.17 Almond
16.3.5.2 Amido phthalic acid
16.3.3.1 Ambrettolide
16.3.6.8 Anethole
16.2.2.2 Apiole
16.2.2.3 Apiol
16.2.2.4 Asarone
16.4.7.2 Bergenin
16.3.6.18 Bitter almond
16.4.7.3 Caffeic acid
16.3.6.6 Camphor
16.2.2.5 Carpacin
16.3.6.4 Castor oil
16.3.10.3 Chavicol
16.2.2.7 Chevibetol
16.3.2.1 Chloral
16.3.6.9 Clove oil, eugenol
16.3.2.5 Cucumber aldehyde
16.3.2.2 Decanal
16.3.3.2 Diacetyl
16.2.2.8 Dillapiole
16.2.2.9 Elemicin
16.3.6.16 Ellagic acid
16.3.5.3 Eosin
16.3.6.15 Epigallocatechin
16.6.1 Essential oils
16.3.6.10 Eugenol
16.3.6.11 Eugenol acetate
Estragole, C10H12O, methyl chavicol
16.3.6.9 Eugenol
16.6.2 Fixed oils
16.3.5.4 Fluorescein
16.3.5.0 Fluorescent liquids
16.3.5.5 Fraxin
16.3.6.19 Gallic acid
16.3.6.7 Gingerol
16.3.6.21 Isoeugenol
16.3.6.22 Isosafrole
16.3.10.1 Juglone
16.3.3.0 Ketones
16.3.5.6 Magdala red
16.3.10.5 Methyl eugenol
16.3.6.12 Methyl isoeugenol
16.3.3.3 Muscone
16.3.6.13 Myristicin
16.3.2.3 Nonanal
16.3.2.4 Nonenel
16.3.6.14 Nothoapiole
16.6.0 Oils, essential oils, fixed oils, vegetable oils
16.3.2.8 Oxidation of methanol to methanal
16.2.2.1 Phenylpropenes
16.3.10.2 Pindone
16.6.0 Plant oils, essential oils, fixed oils, vegetable oils
16.3.2.6 Prepare ethanal with potassium manganate (VII)
16.3.2.7 Prepare ethanal with potassium dichromate
16.3.6.20 Propyl gallate
16.3.5.7 Quinine
16.3.10.0 Quinones
16.3.5.8 Safranin
16.3.10.4 Safrole
16.4.7.1 Salicyclic acid
16.3.6.7 Shogaol
16.4.6.0 Tests for gases from burning hydrocarbons
16.4.5.0 Tests for organic compounds
16.6.3 Vegetable oils
16.3.6.7 Zingerone

16.3.3.0 Ketones
16.3.3.0 Ketones
16.3.3.2 Diacetyl
16.3.3.3 Muscone

16.6.0 Plant oils, essential oils, fixed oils, vegetable oils
16.6.1 Essential oils
16.6.1a List of essential oils
16.6.2 Fixed oils
16.6.2a List of fixed oils
16.6.3 Vegetable oils
16.6.3a List of vegetable oils
Alliin, Allyl disulfide, Asarinin, Diallyl disulfide

16.2.2.1 Phenylpropenes
Phenylpropenes, phenylpolypropanoids, allylbenzenes
phenylpropenes have a propene substituent bound to a phenyl group.

16.2.2.2 Apiole
Apiole, C12H14O4, phenylpropene, in Fennel
in dill, celery, parsley seeds, distilled essential oil of Parsley Petroselenium crispum
in Sassafras albidum (sassafras), called parsley apiol or parsley camphor, green crystals reduced by steam from oil of parsley
essential oil used to treat menstrual disorders, an irritant, may be toxic in high doses causing liver and kidney damage.
In Rock samphire (Crithmum maritinum), camphor wood (Cinnamomum camphorum), Matico (Piper angustifolium)

16.2.2.3 Apiol
Apiol, C12H14O4, phenylpropene derivative, oleoresin of parsley, liquid apiol, green oil of parsley
extracted oleoresin from Parsley, so not essential oil, irritant, kidney damage, dangerous abortifacient.

16.2.2.4 Asarone
See diagram: Asarone
Asarone, C12H16O3, a phenylpropanoid, alpha-asarone and beta-asarone, volatile fragrant oil, fungicide, bacteriocide, spasmolytic,
anti-algal, animal carcinogen, insect attractant and chemosterilant, in Sweet flag
Alpha-asarone (trans-isoasarone), in Asarum, and Carrot seed
Beta-asarone, antifungal, in Acoris bitters, but may be carcinogenic.
In Acorus calamus, (calamus oil banned in USA), Asarum europaeum, Matico (Piper angustifolium)

16.2.2.5 Carpacin
Carpacin, C11H12O3, a phenylpropanoid, isosafrole methyl ether, insecticide, weakly sedative, in Carpano tree, Cinnamomon iners, Lauraceae.
In Prostrate justicia (Justicia prostrata) folk medicine antidepressant

16.2.2.7 Chevibetol
Chevibetol, C10H12O2, a phenylpropanoid, m-eugenol, Betel pepper.

16.2.2.8 Dillapiole
Dillapiole, C12H14O4, a phenylpropanoid related to Apiole, in Dill weed | fennel root Fennel
in coriander, Anethum sowa , Anethum graveolens as dill oils, in Piper species, seeds of Bunium persicum (black caraway)
and many other plants.
Dillapiol is a benzodioxole which have a benzene ring fused to an isomer of dioxole.

16.2.2.9 Elemicin
Elemicin, C12H16O3, phenylpropene, in Elemi (Canarium, in carrot, elemi oil and nutmeg.
In Aniba, Boronia, Croton, Cymbopogon, Dalbergia, Melaleuca, Monopteryx

16.3.2.0 Aldehydes
1.5 Aldehydes, List of aldehydes
16.3.2.0 Aldehydes, alkanals
Cinnamaldehyde
16.3.2.3 Nonanal
16.3.2.2 Decenal
Experiments
16.3.7.2 Oxidation of glucose, blue bottle experiment
16.3.2.8 Oxidation of methanol to methanal
16.3.2.7 Prepare ethanal with potassium dichromate
16.3.2.6 Prepare ethanal with potassium manganate (VII)
9.142.2 Tests for aldehydes with Fehling's solution
16.3.7.3 Tests for aldehydes, Tollens' test.

16.3.6.4 Castor oil
Albuminous seed, castor oil plant: 9.5.4.1
Castor oil bush, Ricinus
9.5.4.1 Castor bean
Decanedioic acid, HOOC(CH2)8COOH
16.3.1.0 Castor oil, ricinoleic acid (experiments)
19.3.24 Castor oil drop (Physics)
31.7.17 Fur in mineral oil shows electric fields
29.2.2.12 Iron filings on overhead projector (Physics)
16.3.17 Lectins, sugar-binding proteins
19.7.2 Lipstick
31.8.1.3 Parallel plate capacitor, electroscope (Physics)
Ricin
9.3.14 Tests for lipase, castor oil seeds, milk
17.3.13 Viscosity and temperature, (Physics)
E476 Polyglycerol polyricinoleate (from mature castor plant)
Saturated carboxylic acid, decanedioic acid, HOOC(CH2)8COOH, sebacic acid, from castor oil.

16.3.5.0 Fluorescent liquids
16.3.5.1 Aesculin, escalin
16.3.5.2 Amido phthalic acid
16.3.5.3 Eosin Y, bromoeosin
16.3.5.4 Fluorescein
16.3.5.5 Fraxin
16.3.5.6 Magdala red
Quinine
16.3.5.8 Safranin (safranine, safranin O).

16.4.5.0 Tests for organic compounds
16.3.7.3 Tests for aldehydes, Tollens' test
9.137 Tests for fats and oils
16.4.6.0 Tests for gas from burning hydrocarbons
16.4.1.0 Tests for organic acids and alcohols
16.4.5 Tests for fats, proportion of fats in foods
16.4.7.0 Tests for saturated hydrocarbons, bromine water tests for unsaturation
16.4.9.0 Tests for saturated hydrocarbons, acidified potassium manganate (VII) solution.

16.3.1.0 Castor oil, ricinoleic acid
(Castor, Greek; beaver, sacs in the groin contains substance similar to castor oil and formerly used to treat constipation) Castor oil
ricinus oil, a fixed oil, from Ricinus communis , Euphorbiaceae, castor oil bush, castor bean, castor oil plant, kikayon, ricinine
endosperm has aleurone grains and oil globules, fatty reserves as a liquid oil, mainly ricinoleic acid, laxative, herbal remedy.
The fruit of the castor bean, Ricinus , suddenly split apart to throw out seeds.
Seeds contain ricin, a highly toxic protein, LD50 22 micrograms per kg, supposed to be developed for warfare and poisoning
prominent people.

1. Ricinoleic acid
Ricinoleic acid, 12-Hydroxy-cis-9-octadecenoic acid, 12-Hydroxyoleic acid, CAS Number 141-22-0, Molecular Weight 298.46
C17H32(OH)COOH, CH3(CH2)5CH(OH)CH2CH=CH(CH2)7COOH.

2. E476 Polyglycerol polyricinoleate
E476 Polyglycerol polyricinoleate (polyglycerol esters of inter-esterified ricinoleic acid from mature castor plant) (emulsifier)
Saturated carboxylic acids, Decanedioic acid, HOOC(CH2)8COOH, sebacic acid, from castor oil.

3. Castor beans
Castor beans contain two toxic proteins, so the castor plant is a poisoning hazard to children and pets.
A single castor bean seed may be fatal for a child if it is masticated and chewed.
1. Ricin is a very toxic protein.
One milligram can kill a human adult.
Ricin may be both a chemical and biological weapon and is explicitly prohibited by the Biological and Toxin Weapons Convention
(BTWC).

4. RCA (Ricinus communis agglutinin)
RCA (Ricinus communis agglutinin), is a toxic protein that agglutinates red blood cells.
In other words, injection of RCA into the bloodstream essentially causes a person's blood to coagulate.
Ingestion of a castor bean or its products will release ricin, but the RCA cannot cross the intestinal wall.
Castor oil contains very little ricin or RCA.

5. Castor oil experiments
Tests for lipase activity, castor oil, milk: 9.3.14 (Tests)
Butanedioic acid (succinic acid): 16.3.6.1.8
Albuminous seed, castor oil plant: 9.5.4.1
Castor oil drop (Physics): 19.3.24
Fur in mineral oil shows electric fields (Physics): 31.7.17
Iron filings on the overhead projector (Physics): 29.2.2.12
Lectins: 16.3.17
Lipsticks: 19.7.2
Ricin
Viscosity and temperature (Physics): 17.3.13.

16.3.2.0 Aldehydes, alkanals
9.142.2 Tests for aldehydes with Fehling's solution
1. Aldehydes contain the group .CH.O (-CHO), and are formed by partial oxidation of primary alcohols.
2. Name "aldehyde" from Latin for "dehydrogenated alcohols".
3. Names ending in (-al), alkanals, e.g. methanal (formaldehyde) (CH2=O, HCHO), and ethanal (acetaldehyde) (CH3CHO), the
simplest aldehydes.
4. Aldehydes are compounds in the form RC(=O)H, where a carbonyl group (C=O) is bonded to one hydrogen atom attached to the
carbon atom and to one R group.
5. Aldehydes are reducing agents and can be detected with Tollens' test or Fehling's test.

16.3.2.1 Chloral
Chloral, CCl3CHO, chloral hydrate, trichloroacetaldehyde, trichlorethanal, Harmful if ingested, Not permitted in schools, pungent
volatile liquid, hypnotic used as its crystalline hydrate, chloral hydrate.
Chloral hydrate, Cl3CCH(OH)2, trichloroacetaldehyde hydrate, sedative, hypnotic, "prescription only" drug in Australia
Tests for amylose and amylopectin: 9.132a, (See 1.3).

16.3.2.2 Decanal
Decanal, C10H20O, C9H19CHO, CH3(CH2)8CHO, decyl aldehyde, colourless, clear oily liquid, fragrance and flavouring agent
fatty or soapy smell, fatty or fried or citrus taste, breaks down on heating, in coriander, orange peel, citrus, buckwheat.

16.3.2.3 Nonanal
Nonanal, C9H18O, CH3(CH2)7CHO, nonanaldehyde, pelagonaldehyde, flavouring agent
Colourless to pale yellow, oily liquid, in some perfumes, rose-orange waxy odour, citrus taste.
In rose and citrus oils and pine oils.

16.3.2.4 Nonenel
Nonenel, C9H16O, 2-Nonenal, trans-2-nonenal (not noneal!), colourless liquid, aroma of aged beer, buckwheat.

16.3.2.5 Cucumber aldehyde
Cucumber aldehyde, C9H14O, violet leaf aldehyde, 2, 6-nonadienal (2E, 6Z)-nona-2, 6-dienal, flavour and fragrance agent, odour of
violet leaf, cucumber, green vegetable odour
Violet-leaf aldehyde in cereals, cherry, melon, peas, cooked potato, milk, fish, black tea, oyster, clam
has cucumber smell, in cucumber juice, used as flavouring agent.

16.3.2.6 Prepare ethanal with potassium manganate (VII)
Add one drop of 1% potassium manganate (VII) to five drops of ethanol and ten drops of dilute sulfuric acid.
Heat gently.
The purple colour disappears as potassium manganate (VII) solution is reduced to manganese (II) sulfate.
Note the odour of an acetaldehyde.
CH3CH2OH + (O) --> CH3CHO + H2O
2KMnO4 + 3H2SO4 + 5CH3CH2OH --> K2SO4 + 2MnSO4 + 8H2O + 5CH3CHO.

16.3.2.7 Prepare ethanal with potassium dichromate
Add two drops of 0.1 M potassium dichromate solution to two drops of ethanol and ten drops of dilute sulfuric acid.
Heat gently.
The orange potassium dichromate solution turns green showing the presence of Cr3+.
The reaction forms ethanal then ethanoic acid (acetic acid).
Note the odour of an acetaldehyde.
C2H5OH + (O) --> CH3CHO + H2O
ethanol + (oxygen) --> ethanal + water
CH3CHO + (O) --> CH3COOH
ethanal + (oxygen) --> ethanoic acid
K2Cr2O7 + 4H2SO4 + 3CH3CH2OH --> K2SO4 + Cr2(SO4)3 + 7H2O + 3CH3CHO.

16.3.2.8 Oxidation of methanol to methanal
Oxidation of methanol to methanal, platinum catalyst
See diagram 16.3.3: Oxidation of methanol
Be careful! This experiment may be too dangerous for a school science laboratory.
Test the experiment in the science preparation room before demonstrating it in the classroom.
Do not let anyone look down into the flask if the experiment appears not to be working!
Put 10 mL methanol in a flask and heat briefly with a Bunsen burner.
Heat a piece of platinum wire connected to a copper wire until it is red hot.
Hook a copper / platinum wire inside the flask to start the reaction.
Heat the wire again if the reaction does not start.
The reaction continues till all the MeOH is used up.
To stop the reaction, remove the catalyst platinum wire catalyst.
Be careful!
The methanol is oxidized to methanal when the vapour reaches a certain concentration accompanied by a loud "whoosh" sound as the
vapour burn and leaves the flask.
The copper T-piece acts as a chimney allowing entry of air when the vapour bums.
The Pt wire changes from red-hot to silver.
CH3OH + O2 --> CH2O + H2 (Pt catalyst)
CH2O + O2 --> CO2 + H2O (Pt catalyst).

16.3.3.1 Ambrettolide
Ambrettolide, C16H28O2, isoambrettolide, a macrocyclic musk, flavour and fragrance agent, colourless to pale yellow
liquid, sweet soapy musk odour and taste, food additive, a macrolide having a lactone ring of at least twelve members with large
macrolactam rings.

16.3.3.2 Diacetyl
Diacetyl, CH3COCOCH3, butanedione, dimethyldiketone
Diacetyl is used in the popcorn industry to give a butter or butterscotch flavour and creamy odour to popcorn sold in bags.
However, workers in the popcorn industry have reported medical problems with their respiratory systems, particularly the lungs, leading
to workers compensation.
Heating bags of popcorn in a microwave oven causes similar problems.
The popcorn industry is considering not using diacetyl in bagged products.

16.3.3.3 Muscone
Muscone, C16H3O, methylcyclopentadecanone, main contributor to musky smell, flavouring ingredient, perfume fixative musk from musk
deer but is now produced artificially.

16.3.5.1 Aesculin
Aesculin, C15H16O9, escalin
Aesculin, coumarin glucoside, in Horse chestnut tree (Aesculus hippocastanum), Hawthorn (Crataegus oxyacantha), and
Bursaria spinosa
It is used to identify Enterococcus bacteria.
It gives pale blue colour by reflected light and straw colour by transmitted light.
Causes gastroenteritis, muscle weakness, diarrhoea, but used in blood-thinning treatment e.g. for haemorrhoids.

16.3.5.1a Aescin
See diagram: Aescin
Aescin, escin, C55H86O24, pentacyclic triterpenoid saponin, the main saponin of more tha 30 different saponins in seeds of Aesculus,
used to treat blood vessel disorders, reduce inflammation, oedema, pain, inhibits aedema, treats vascular fragility
Horse chestnut tree Aesculus hippocastanum leaves.

16.3.5.2 Amido phthalic acid
Amido phthalic acid, amido-tarephthalic acid, 2-[(3-bromobenzene)amido]benzoic acid, C14H10BrNO3
4-aminophthalic acid gives pale violet colour by reflected light and pale yellow colour by transmitted light.
Amido-tarephthalic acid gives bright green colour by reflected light and pale green colour by transmitted light.

16.3.5.3 Eosin
Eosin Y, bromoeosin, C20H6Br4Na2O5, tetrabromofluorescein, Solvent Red 43, Japan red 223, red fluorescent dye, from bromine
reaction with fluorescein, histological stain
Eosin, eosine, bromoeosin, gives yellow green colour by reflected light and orange colour by transmitted light.
It is formed by reaction of bromine with fluorescein, the potassium salt of tetrabromo-fluorescein, sodium-2, 4, 5, 7-tetrabromofluorescein
Eosin Y has yellowish colour, and eosin B (Acid red), has bluish colour.
It is used as a counter stain to haematoxylin for microscopic examination.
Eosin, an acidic dye, stains cytoplasm stained orange pink and haematoxylin, a basic dye, stains nuclei blue or purple where nucleic
acids mainly occur.
Eosin stains red blood cells intensely red.

16.3.5.4 Fluorescein
| See: 1.5: Fluorescein biology solution
| See diagram 16.3.1.1: Fluorescein
| See diagram 7.9.56.1: Fluorescein
Fluorescein gives intense green colour by reflected light and orange yellow colour by transmitted light.
Fluorescein, 1, 3-dihydoxybenzene phthalein, [2-(6-hydroxy-3-oxo-xanthen-9-yl), benzoic acid], C20H12O5, is red crystals that can
dissolve in alkali to form a red colour and green fluorescence.

16.3.5.5 Fraxin
Fraxin gives blue-green colour by reflected light and pale green colour by transmitted light.
It is a colourless glucoside found in the bark of the ash tree, Fraxinus .
Fraxin and aesculin are two coumarins found in Actinidia chinensis and Actinidia deliciosa (kiwi fruit, Chinese gooseberries).

16.3.5.6 Magdala red
Magdala red, phloxine B (tetrabromotetrachloro-fluorescein), acid red 92, gives opaque scarlet colour by reflected light and brilliant
carmine colour by transmitted light.
It is used to identify unhealthy yeast cells.

16.3.5.7 Quinine
Quinine, C20H24N2O2, Quinoline Alkaloid
See diagram 16.3.23: Quinine
See diagram: Quinine.
Quinine is an antimalarial, antipyretic, gives a pale blue colour by reflected light and no colour by transmitted light.
It is extracted from the bark of Cinchona ledgeriana (quinine tree, "fever tree"), and Remijia in South America.
It was formerly an anti-malarial medicine and is still used for treatment of some heart conditions.
As a medicine it was taken in carbonated mineral water, but nowadays is still taken as a beverage called "tonic water",
which is valued for the slightly bitter taste of "gin and tonic".
Tonic water is not a medicine.
However, if quinine is used in a flavouring, even if the flavourings are not identified on the label, quinine must be identified
because some people are hypersensitivwe to it.
UQ Diamantina Institute Postdoctoral Research Fellow Dr Daniel Hwang said in 2019: "Whether you enjoy tonic water or
not, people with bigger brains typically find it less bitter."
"Quinine is a key ingredient in tonic water and is commonly used to assess people's response to a bitter taste."
Cinchona was discovered in the 1630s as a treatment for malaria and, for 350 years, was the only effective cure known
in Europe until synthetic replacements in the 1940s.
Malaria remains today one of the deadliest diseases known throughout the tropics, and until the 20th century the disease
was prevalent throughout Europe, including Britain.
The Cinchona tree is native to the eastern slopes of the Andes, across Ecuador, Peru and Bolivia, and was virtually inaccessible
for most Europeans during the 17th century.
In the 18th and 19th centuries, demand started to outstrip supply and threats of overharvesting and the desire to control the
source caused competing empires to source this plant.
The Spanish tried to prevent this, but failed to establish their own successful plantations.
So both the Dutch, in Indonesia, and the British, in India, founded government controlled plantations for mass production of quinine.
Fluorescence spectroscopy can be used to determine the percentage quinine content in samples of tonic water or bitter
lemon, by comparing the fluorescence of a sample in ultraviolet light to the fluorescence of a standard quinine sulfate solution containing
10 mg of quinine sulfate in 1L of deionized water.
Large doses of quinine used to treat malaria infection may cause heart problems but small doses, e.g. in a small bottle of tonic water
have been effective in treating leg muscle cramps.
The quinine alkaloid, C20H24N2O2.3H2O, was first extracted from the bark of Cinchona officinalis, Rubiaceae.
Common names include quinine bark, China bark, Peruvian bark, Jesuit's bark, fever tree.
Cinchona ledgeriana and Cinchona succirubra produce the highest quantity of quinine alkaloids, but nowadays mostly synthetic.
Quinine dihydrochloride monohydrate
Quinine hydrochloride dihydrate
Benzoquinone, C6H4O2, para-quinine, cyclohexadiene-1, 4-dione, in coal smoke
Quinidine, antiarrhythmic, in Cinchona ledgeriana (quinine tree)
Alkaloid: 7.9.4.1
Amines and alkaloids: 16.3.0.0
Poisons and First Aid: 3.10.0 (Table)
Quinoline group of alkaloids: 16.3.23.
Quinine hemisulfate monohydrate and dihydrate, Quinine hydrochloride dihydrate, Quinine sulfate

Bitter taste experiment.
Replace quinine with cold tea solution and note the difference in taste
Quinine iodosulfate, Dichroic polarization colours: 27.82
Sense of taste, the gustatory system: 9.246
Taste, smell, flavour: 19.3.1.

16.3.6.6 Camphor
See: Cinnamomum species
Camphor, C10H16O, bicyclic monoterpene ketone, DL-Camphor, colourless to white crystalline powder, "mothball" odour, original
source was in camphor laurel, skin antipruritic, anti-infective, moth-proofing safer alternative to naphthalene and
1, 4-dichlorobenzene mothballs.
Natural camphor was distilled from the clippings, wood and roots of the camphor laurel tree, Cinnamomum camphora , and other
species, but nowadays camphor is a synthetic aromatic, produced from vinyl chloride and cyclopentadiene.
Camphor, C10H16O, a crystalline terpenic ketone, complex chemical composition, highly flammable, Harmful if ingested
DL-camphor is natural camphor.
Camphor oil has many constituents, including borneol | camphene | carvacrol | cineole | citronellol.
Do not inhale hot fumes of camphor, because the terpenic ketone camphor can be highly toxic.
Camphor types:
Brown camphor contains safrol, terpinol
White camphor contains cineol, pinene, not safrol
Yellow camphor contains safrol, sesquiterpenes.
Camphor is used as a topical rubefacient / counter-irritant medication.
It is a common ingredient of anti-itch and heat-rub medicines, e.g. Haw Par Tiger Balm.
Camphor, Rubefacient, Cinnamomum camphora (camphor tree), Harmful if ingested
Camphor repels clothes' moths and cats and is used to make gunpowder and celluloid.
Celluloid is cellulose nitrate plasticized with camphor.
Use D-Camphor instead of naphthalene moth balls to protect clothes from moths and silverfish.
Prepare camphor oil: 19.6.7
Prepare thionyl chloride, SOCl2: 12.18.3.2
Drive a boat with surface tension, camphor boat, spinning dancers: 19.1.3
Terpenes (C10H16): 16.3.5.1.

16.3.6.7 Gingerol, [6]-Gingerol, [8]-Gingerol, [10]-Gingerol
Gingerol, 6-gingerol in ginger rhizome, C17H26O4, phenol, yellow oil, antioxidant, anti-inflammatory, antitumour, anti-nausea, anti-carcinogenic
Gingerols include the 6-, 8-, 10-, 12- gingerols, whicht are easily altered by cooking or drying.
Cooked ginger is less pungent than fresh ginger, gingerols --> zingerones
6-gingerol, C17H26O4 --> zingerone, vanillyl acetone, C11H14O3
Zingerone, the pungent principle of ginger, only slightly pungent, sweet spicy aroma, is used in imitation fruit flavours, ginger beer, ginger ale,
gingerbread, and occurs in fruits, e.g. cranberry, raspberry, mango.
Dried ginger is more pungent than fresh ginger, gingerols --> shogaols,
6-gingerol, C17H26O4 --> 6-shogaol, C17H24O3
Ginger rhizome: Ginger (Zingiber officinale), Zingiberaceae.
See diagram: Gingerol

16.3.6.8 Anethole
See diagram: Anethole
Anethole, C10H12O, trans-anethole, monoterpene, CH3CH=CHC6H4OCH3, phenylpropanoid, phenylpropene derivative,
4-propenylanisole, isoestragole, anise camphor, unsaturated ether, hydrophobic terpene, white crystals or liquid, very
slightly soluble in water.
Annise camphor, very sweet (13 times sweeter than sugar), aromatic flavour of anise and fennel, odour of anise oil
Anethole occurs in | Anise | Anise myrtle | Fennel | Star anise.
Oil of aniseed in alcoholic beverages, absinthe, anisette (anis), arak, champurrado (atole de anis), ouzo, pastis, Pernod, raki
sambuca and some non-alcoholic root beers.
trans-Anethole in essential oils of star anise, anise seed oil, sweet fennel, flavour of of candy, ice cream chewing gum.
Anethole is estrogenic at lower concentration, but cytotoxic at higher concentrations.
Anethole is anti-microbial and anti-fungal, and is used as insecticide, mosquito repellent
7.6.01 Ouzo effect, microemulsions, hydrophobic terpene.

16.3.6.9 Clove oil, eugenol
Clove oil, eugenol, C10H12O2
Clove oil, analgesic and antiseptic, used in dentistry for its main ingredient eugenol, home remedy for toothache, sold in pharmacies
Oil of cloves, eugenol, 2-methoxy-4-(2-propenyl) phenol, an allyl benzene from dried flower buds (inhibits mould, relieves toothache
insecticide, cooking ingredient, high concentration of antioxidants, spice, Indonesian clove and tobacco cigarettes, fish killer, repels
ants, herbicide is toxic at low concentrations, harmful if large quantity ingested (eugenol also in nutmeg, cinnamon, bay leaf)
relative density 1.04 -1.06 so does not float on water, clove oil contains eugenol and caryophyllene, used in dentistry, from Eugenia
caryophyllus , Myrtaceae.
In Clove.

16.3.6.10 Eugenol
See diagram: Eugenol
C10H12O2, phenylpropene, 4-allyl--2-methoxyphenol, 2-methoxy-4-(2-propenyl)phenol.
Eugenol, clove oil, mint camphor, is found in essential oils, e.g. cinnamon, clove oil, pimento, nutmeg, bay leaf.
It has a pleasant, spicy, clove-like odour and taste, but will darken and thicken when exposed to air, slightly soluble in water.
It is used in perfume, flavourings, medicine, local antiseptic and anaesthetic in dentistry.
Eugenol may cause liver damage and some people are allergic to it.
Formerly it was used in the production of isoeugenol for the manufacture of vanillin.

16.3.6.11 Eugenol acetate
Eugenol acetate, C12H14O3, eugenyl acetate, acetyl eugenol, colourless to pale yellow, flavouring agent, floral flavour, in clove oil,
caraway, cinnamon leaf, spicy odour.

16.3.6.12 Methyl isoeugenol
Methyl isoeugenol, C11H14O2, phenylpropene
may cause allergic skin reaction.

16.3.6.13 Myristicin
Myristicin, C11H12O3, phenylpropene, in Nutmeg essential oil.

16.3.6.14 Nothoapiole
Nothiapole, C13H16O5, phenylpropene, in Perilla.

16.3.6.15 Epigallocatechin
Epigallocatechin gallate, epigallocatechin 3-gallate (EGCG), C22H18O11, in green tea, ester of epigallocatechin and gallic acid.

16.3.6.16 Ellagic acid
Ellagic acid, C14H6O8, from hydrolysis of tannins, antioxidant, antiproliferative, dietary supplement, in Oak trees and foods, e.g. walnuts.

16.3.6.17 Almond
Almond (Prunus dulcis, syn. Prunus amygdalus), Rosaceae
in Bible Numbers 17:8, India, North Africa, world wide
Fruit is a drupe, eaten raw or cooked, green or mature, whole or sliced or ground, as almond oil,
almond butter, almond milk, in marzipan, nougat, cookies, cakes.
Source of nutrients especially antioxidant vitamin E.
Almond extract flavouring purchased in small bottles used in cooking, contains benzaldehyde from Cassia bark,
but no cyanide.
See diagram Almond self-pollinating, Daley's Fruit Trees
See diagram Dwarf almond, Daley's Fruit Trees

16.3.6.18 Bitter almond
Bitter almond, Prunus dulcis var. amara
The essential oil mostly contains benzaldehyde causing bitter taste, and is used for cleaning bone and ivory.
When almonds are damaged or bitten, enzymes convert the glucoside amygdalin to benzaldehyde and cyanide.
So the essential oil contains mostly benzaldehyde and some cyanide.
Bitter almonds or bitter almond essential oil is toxic, not to be ingested and may irritate skin, but in Europe may be added as spice to
flavour marzipan, amaretto cookies and liqueur.
Mandelic acid, C8H8O3, C6H5CH(OH)CO2H, hydroxyphenylacetic acid, in bitter almonds, urinary infection.

16.3.6.19 Gallic acid
Astringent phenolic acid, Toxic if ingested
Gallic acid, C6H2(OH)3COOH, [C6-C1], (a trihydroxybenzoic acid), C7H6O5, 3, 4, 5-trihydroxybenzoic acid, a water-soluble
phenolic acid
It is found in gall nuts (Quercus) | sumac (Rhus) | witch hazel | tea plant (tea leaves)
It is an antioxidant, and is anticarcinogenic, antiangiogenic, anti-inflammatory, anti-fungal and anti-viral
It is formed by fermentation of tannic acid in nature.
Gallates are salts and esters of gallic acid.
The esters and polyesters of gallic acid are very widely distributed in angiosperms, as gallotannins, tannins, catechin gallates, aliphatic
gallates, and have similar properties to gallic acid.

16.3.6.20 Propyl gallate
Propyl gallate, C10H12O5, propyl 3, 4, 5-trihydroxybenzoate, ester from condensation of gallic acid and propanol, food additive E310,
radical scavenger functions, white to creamy-white crystalline powder, odourless or faint odour, insoluble in water, slightly bitter taste,
antioxidant added to foods containing oils and fats to prevent oxidation, in maize, vegetable oils, animal fats
Propyl gallate, antioxidants: See diagram 19.2.1.6
Propyl gallate, anti-fade reagent reduces photobleaching of fluorescence microscopy probes, e.g. fluorescein.

16.3.3.0 Ketones
Ketones (=CO) (-one), e.g. propanone (acetone) (CH3C=OCH3)
9.142.2 Tests for aldehydes with Fehling's solution
Ketones have a carbonyl group (C=O), bonded to two carbon atoms in the form R2C=O, but neither R may be H.
Ketones contain the ketone group (-CO-).
It is a carbonyl group with two single bonds to other carbon atoms.
Propanone (acetone, CH3COCH3), and butanone (CH3COC2H5, methyl ethyl ketone), are the simplest saturated ketones (R1COR2).
Ketone names end with "-one".
Ketones cannot be detected with Tollens' test or Fehling's test.

16.3.6.21 Isoeugenol
Isoeugenol, C10H12O2, phenylpropanoid, 4-propenylguaicol, related to phenylpropene
clear to pale yellow oily liquid, extracted from clove oil and cinnamon oil, slightly soluble in water, spicy odour and taste of cloves
prepared from eugenol by heating, used in perfumes, flavourings, local antiseptic and analgesic, used to make Vanillin
Eugenol derivatives or methoxyphenol derivatives used in perfumers and flavourings, insect attractants, UV absorbers, analgesics,
biocides and antiseptics, stabilizers and antioxidants for plastics and rubbers.
In Ylang ylang essential oil Ylang ylang, (Cananga odorata) | Nutmeg (Myristica fragrans) fruit | Rocky Mountain juniper
(Juniperus scopulorum) pine needles |

16.3.6.22 Isosafrole
Isoafrole, C10H10O2, phenylpropanoid, related to phenylpropene,
colourless fragrant liquid, anise odour of anise, in root beer and sarsaparilla flavours.
Used to make heliotropin and in oriental perfumes
Like Safrole, herbal remedy used for liver regeneration but moderate poison.
In Ylang ylang essential oil Ylang ylang, (Cananga odorata) | essential oil of Ligusticum acutiloba | leaves of the curry tree (Murraya koenigii) |
16.3.10.0 Quinones
Quinones, quinone, hydroquinone, juglone
See diagram 16.1.4.3: Quinones | See diagram 16.3.5.0: Quinones, Pindone sodium salt
1. The chemical called "quinone" usually refers to the simplest quinone, the yellow crystalline molecule, C6H4O2, 1, 4-benzoquinone
p -benzoquinone, para-quinine, para-quinone, cyclohexadiene-1, 4-dione, used for preparing dyes, tanning hides, and photography
bright yellow crystals, in coal and tobacco smoke, in Iris kemaonensis
2. Quinones contain the C=O groups in an unsaturated ring, as 1, 2-quinones and 1, 4-quinones (e.g. cyclohexandiene-1, 4-dione)
cyclic dione structure, conjugated diketones, e.g. benzoquinone, by conversion of -CH= groups into -C(=O)- groups.
3. Quinones are aromatic compounds in plants.
All quinones are coloured, many are plant pigments, e.g. lawsone from Lawsonia inermis the orange dye henna, and juglone from
walnut shells, Juglans regia .
4. Quinones are formed from oxidation of hydroquinone and in pecan nuts, and are used in dyes.
5. Hydroquinone (1, 4-dihydroxybenzene), C6H4-1-4-(OH)2, is used in photography developers, also coenzymes in animal and plant
cells, and plastoquinones involved in photosynthesis, and vitamin K.
Hydroquinone, C6H4(OH)2, hydroquinol, 1, 4-dihydroxybenzene, 1, 4-benzenediol quinol, photographic developer, Toxic if ingested
Hydroquinone, benzene-1, 4-diol, quinol, Solution < 25% Not hazardous.

16.3.10.1 Juglone
Juglone, C10H6O3
1, 4-napthoquinone, C.I. Natural brown 7, C.I. 7550, is produced by some trees in the walnut family, e.g. black
walnut, Persian walnut, butternut, and pecan, and is leached or released into the soil.
Juglone has fungicide and insecticide properties, but it is toxic to many plant species.
Juglans regia , walnut tree, common walnut, English walnut, Persian walnut, the quinone juglone, walnut shells, oxidation of
hydroquinone, Juglandaceae.

16.3.10.2 Pindone
Pindone, C14H14O3
See diagram 16.3.5.0: Quinones, Pindone sodium salt
Pindone (ISO 1750) (2-pivaloylindan-1, 3-dione), is an anticoagulant drug used to control rodents and rabbits
e.g. "Bunnybait" is 0.5 g /kg sodium salt of pindone is used as an oat bait for rabbits, C14H13NaO3.

16.3.10.3 Chavicol
Chavicol, C9H10O, p-allylphenol, a phenylpropene, in betel oil, Areca catechu, betel nut palm.

16.3.10.4 Safrole
Safrole, C10H10O2, a phenylpropene, colourless-yellow oil, aroma of "sweet shops", a heptocarcinogen that cause permanent liver
damage
Safrole is genotoxic compound in root of Sassafras tree (Sassafras albidum), Brazilian sassafras (Octea odorifera), and quid of Areca
catechu, betel nut palm.
Safrole-DNA adducts which, induce chromosomal variations, found in oral cancers of Areca users.
Safrole is the principle constituent of sassafras oil and brown camphor oil.

16.3.10.5 Methyl eugenol
Methyl eugenol, C11H14O2, allylveratrol, methyl ether of eugenol.

Experiment
Kill black mould
Grow mould on bread and place a few drops of a solution of it on a nutrient agar plate and then incubate it.
Measure the size of the colony after a few days and then place a square of filter paper on the agar with various amounts of clove oil
added and note the growth over the next week.
A solution of 2.5 mL of clove oil to 1 litre of water should kill the spores 24 to 48 hours.
Grow moulds at different concentrations of clove oil, from zero to 100% oil.

16.4.6.0 Tests for gases from burning hydrocarbons
Hydrocarbons burn in excess air to form carbon dioxide and water.
The reaction is exothermic.
Methane burns with a clear flame.
Ethene (ethylene) and ethyne (acetylene) burn with a smoky luminous flame.
This flame can be seen above a chimney at many petrol refineries where excess ethene is burned off.

Experiment
Light a natural gas burner or pour drops of cigarette lighter fuel in an evaporating basin and ignite it.
Hold a dry test-tube containing ice over the burning gas.
Water from the combustion condenses on the test-tube.
Add lime water and shake.
The milky precipitate shows the presence of carbon dioxide.
CH4 (g) + 2O2 (g) ---> CO2 (g) + 2H2O (g)
In insufficient oxygen, the poisonous gas carbon monoxide forms.
2CH4 (g) + 3O2 (g) ---> 2CO (g) + 4H2O (g).

16.4.7.1 Salicyclic acid
Salicyclic acid, hydroxybenzoic acid C7H6O3, [C6-C1], 2-Hydroxybenzoic acid, C6H4(OH)COOH, Harmful, skin irritant
Salicyclic acid is a bitter-tasting derivative of phenol, used to make fungicides and Aspirin, acetylsalicyclic acid.

16.4.7.2 Bergenin
Bergenin, C14H16O9, cuscutin (a trihydroxybenzoic acid glycoside), antitussive, anti-inflammatory, protects against liver
disorders, in Bergenia species, Ardisia japonica.

16.4.7.3 Caffeic acid
Caffeic acid, C9H8O4 (HO)2C6H3CH=CHCO2H, 3,4-dihydroxycinnamic acid, antioxidant, anti-inflammatory, widespread occurrence,
in yarrow Achillea, Anthemis, Coffea, Cinchona, Conium, Digitalia, in PapaverPapaver, Taraxacum, burdock, hawthorn, artichoke,
pear, basil thyme, oregano, apple.

16.6.1 Essential oils
Essential oils, volatile oils, ethereal oils
Essential oils are not really "oils", i.e. not smooth, sticky liquids, immiscible in water, but are volatile oils obtained by distillation and
having the characteristic odour of the plant from which it is extracted.
A "note" is a term used in perfumery, meaning any of the basic components of a fragrance of a perfume which give it its character.
Reference: The Encyclopedia of Essential Oils , by Julia Lawless, Thorsons, Harper Collins, 2002
ISBN 0 00 7145187
1. An essential oil is a concentrated, hydrophobic liquid that volatilizes on heating without decomposition to form the distinctive scents
of plants.
Essential oils are used in aromatherapy and in religious ceremonies requiring the burning of incense.
2. They are usually liquid, but may be solid, e.g. orris, or semi-solid, e.g. rose.
3. On exposure to air, they do not harden, but, unlike fixed oils, evaporate, leaving no oily residue.
4. They dissolve in alcohol, fats and oils, but not in water.
5. They are mainly volatile mixtures of terpenes and terpenoids, but also may contain esters, aliphatic and aromatic esters, phenolics
and substituted hydrocarbons formed in plant oil glands.
6. Essential oils are not recommended for pregnant women.
7. For consumption recipes, buy only top quality essential oils from a reputable source.
Buy "Therapeutic" grade or "Food Grade" and never buy perfume grade or or diluted or solvent extracted essential oils.
8. Essential oils include rose oil, jasmine oil, oil of cloves, lavender oil, peppermint oil, eucalyptus oil, ylang-ylang oil (Cananga odorata)
and the cheap citrus oils, e.g. lemon oil, sweet orange oil.
They are extracted by distillation, expression and solvent extraction.
They cause plant odours, some of which can be distilled to form perfumes, cosmetics, bath products, flavouring food and drink
flavourings, incense scents and substances that deter insects and herbivores from damage or grazing.
9. Volatile oils
An essential oil is usually regarded as a volatile oil produced by distillation with the odour characteristic of the distilled plant material.
However, the term is often used loosely in the herbalist and aromatherapy industries to describe any usually aromatic extracts from
plant material.
10. Extraction
Plant material --> (distillation) --> "distilled essential oils".
Plant material --> (expression, i.e.
pressing and squeezing) --> "citrus oils".
Plant material --> (solvent extraction) --> "concretes" --> "absolutes".
Plant material --> (solvent extraction) --> "resinoids".
Plant material --> ("enfleurage") --> "pomades --> "enfleurage absolutes".
Concretes
The "concretes" are extracted from raw previously-living plant material with hydrocarbon solvents, not steam distillation, and are
usually about 50% wax and 50% volatile oil, e.g. jasmine.
The oil ylang ylang is 20% wax and 80% essential oil.
The term "concretes" may refer to the fact that they are more concentrated and stable than distilled essential oils.
Resinoids
The "resinoids " are extracted from dead resinous material with hydrocarbon solvents to produce balsams, resins, oleoresins, oleo
gum resins.
Absolutes
The "absolutes" are extracted from the "concretes" by further solvent extraction using "absolute alcohol" (pure ethanol) to remove most
of the wax.
Nowadays more pure "absolutes" are produced with liquid carbon dioxide.
Pomades
The "pomades" were once produced by pressing cut flowers onto a glass plate covered with odourless fat, a process called "enfleurage".
The volatile oils from the flowers that had diffused into the fat were extracted with alcohol to produce "enfleurage absolutes".
Nature identical
The pharmacy industry can produce most essential oils 96% synthetically, labelling them "nature identical" products.
However, the 4% of natural constituents may be important to the herbalist and aromatherapy.

16.6.1a List of essential oils
HPLC
Agar oil (Aquilaria malaccensis), oodh, Thymelaeaceae.
Ajwain oil (Trachyspermum ammi , Carum copticum), Thymol, Apiaceae.
Allspice oil (Pimenta dioica), Myrtaceae.
Almond oil, bitter almond (Prunus dulcis var. amara).
Angelica root oil (Angelica archangelica), Apiaceae.
Anise oil (Pimpinella anisum), licorice odour, Apiaceae.
Asafoetida oil (Ferula assafoetida), to flavour food, Apiaceae.
Balsam fir needle oil, , Pinaceae
Balm oil, Lemon Balm oil (Melissa officinalis), Lamiaceae
Balm of Gilead (Commiphora gileadensis), Burseraceae.
Balsum of Peru oil (Myroxylon balsamum), flavour food and drink, Fabaceae.
Balsam torchwood (Amyris balsamifera), Rutaceae.
Basil oil (Ocimum basilicum), make perfumes, aromatherapy, Lamiaceae.
Bay oil (Laurus nobilis), make perfumes, aromatherapy, Lauraceae.
Benzoin balsamic resin oil, (Styrax benzoin), Styracaceae.
Bergamot oil (Citrus x aurantium subsp. bergamia, C. bergamia), make perfumes, aromatherapy, Rutaceae.
Birch oil, oil of wintergreen, (Betula lenta), aromatherapy, Betulaceae
Bitter almond oil
Black pepper oil (Piper nigrum), distilled from berries, Piperaceae.
Bois de rose oil, rosewood oil (Aniba rosaeodora), Lauraceae
Borage seed oil (Borago officinalis), Boraginaceae.
Borage oil, Borago officinalis seeds, anti-inflammatory, highest source of γ-linoleic acid
Boldo oil (Peumus boldus)
Boronia oil, absolute oil (Boronia megastigma), Rutaceae
Buchu oil (Agathosma betulina), buchu shrub, toxic, contains diosphenol, Rutaceae
Cade oil, Juniperus oxycedrus, contains cadinene, cadinol, guaiacol, distilled from wood, dark, aromatic, smoky smell, cosmetics,
incense, folk medicine, skin ailments, allergic reactions possible
Cajeput oil, contains cineol, terpineol, pinene, nerolidol, distilled from leaves of Melaleuca cajuputi
Catmint oil Calamint (Calamintha sylvatica), Lamiaceae, cat mint, contains citral, nerol, citronellol, Limonene, geraniol, metatabilacetone,
attracts cats.
Calamus oil, from Acorus calamus, contains beta-asarone, eugenol, banned in USA
Calendula oil, marigold oil
Camphor oil: 16.3.6.6
Camphor of Borneo oil
Cananga oil, contains caryophyllene, safrol, methyl salicylate.
Capers (Capparis spinosa), Capparaceae.
contains carvone terpenoid
Cannabis flower oil, essential oil, food flavouring
Caraway seed oil, contains carvone terpenoid and has its taste, carveol, food flavouring
Cardamom oil (Elattaria cardamomum), Zingiberaceae, contains terpinyl acetate, cineol
Carrot seed oil, contains pinene, carotol, daucol, geraniol, caryophyllene, aromatherapy.
Cascarilla bark oil, contains cymene, diterpene, Cassia, contains cinnamic aldehyde, methyl eugenol (dark brown liquid).
Cassie oil, contains benzyl alcohol, methyl salicylate, fernesol, geraniol.
Cabreuva oil, contains nerolidol.
Calamansi oil
Calamus oil, Calamus
Camphor oil, perfume, food additive, 16.3.6.6 Camphor oil
Canada balsam
Cannabis flower oil
17.1 Capsaicin oil (Capsicum oil) species
Caraway oil (Carum carvi), Apiaceae.
Cardamom seed oil (Elattaria cardamomum), Zingiberaceae.
Carrot seed oil
Cedarwood oil, cedar oil, perfumes
Cedarwood, Atlas Cedarwood, contains atlantone, caryophyllene.
Cedarwood, Texas Cedarwood, contains cedrene, cedrol.
Cedarwood, Virginian Cedarwood, contains cedrene, cedrol.
Celery seed oil (Apium graveolens var. dulce), Apiaceae.
contains Limonene.
Chamomile oil (Matricaria chamomilla), Asteraceae.
Roman and German chamomile oil, azulene
Chamomile (Matricaria chamomilla), Asteraceae.
German Chamomile, contains Chamazulene , C14H16 (a product of distillation), farnesene.
Roman Chamomile, contains angelic acid esters, tiglic acid esters, pinene, nerolidol, cineol, Farnesol
Chervil (Anthriscus cerefolium), Apiaceae
contains methyl chavicol, aromatic unsaturated ether, anethole, anise camphor
Chilli pepper oil (Capsicum), Solanaceae.
Cinnamon oil (Cinnamomum verum), flavouring, Lauraceae.
Cinnamon (Cinnamomum) species, Lauraceae
inner bark for cinnamon sticks (cinnamon leaf oil contains eugenol, cinnamaldehyde
benzyl benzoate) (cinnamon bark oil contains cinnamaldehyde, eugenol, benzyl benzaldehyde, pinene), in Coca Cola.
Cistus oil, Cistus labdanum, essential oil for aromatherapy, Cistaceae
Citron oil (Citrus medica), Ayurvedic aromatherapy, Rutaceae.
Citronella oil (Cymbopogon nardus), lemon grass oil, insect repellent, Poaceae.
Clove oil (Syzygium aromaticum), Myrtaceae
Clove oil, eugenol, Kills black mould: 16.3.6.9
Clove, Syzygium aromaticum, Myrtaceae
Clary sage oil, Salvia sclarea, ancient essential oil, perfume, flavouring, aromatherapy, Lamiaceae
Coconut oil (Cocos nucifera), food, skin and hair, Arecaceae.
Coffee oil (Caffea arabica), flavour food, Rubiaceae.
Coriander oil (Coriandrum sativum), Apiaceae, contains linalool, borneol, geraniol, carvone, anethole
(in Chartreuse and Benedictine liqueurs).
Costus root oil, contains sesquiterpene lactones, e.g. dihyrocostus lactone, cartophyllene, Costaceae
Cranberry seed oil, large cranberry, American cranberry (Vaccinium macrocarpon), Ericaceae.
Contain high omega-3 and omega-6 fatty acics Cubeb oil, Tailed pepper to flavour foods, Java pepper oil, Tailed pepper oil (Piper cubeba).
Cubeb oil, contains sesquiterpenes, monoterpenes (treats amoebic dysentery), flavour foods.
Cumin oil (Cuminum cyminum), Apiaceae.
Cumin (Cuminum cyminum), Apiaceae, contains aldehydes, e.g. cuminaldehyde, also pinenes, farnesine, caryophyllene.
Cypress oil, contains pinene, camphene, cosmetics.
Cypriol oil
Curry leaf oil (Murraya koenigii), Rutaceae.
contains alcohols, e.g. d-borneol, terpenes, e.g. pinene, camphene, flavour food.
Davana oil, Artemisia pallens, davanam, grown for its fragrant leaves and flowers, Asteraceae.
Deertongue oil, essential oil from the leaves of vanilla leaf, Liatris odoratissima, Asteraceae, contains coumarin.
Dill oil (Anethum graveolens), Apiaceae, contains carvone
Diesel Tree oil, Copaifera langsdorffii
Elecampane oil (Inula helenium), Asteraceae.
contains sesquiterpene lactones.
Elemi oil, Canarium luzonicum and Canarium ovatum, contains phellandrene, dipentene, carvone, perfume oleoresins.
Eucalyptus oil (Eucalyptus globulus), Myrtaceae.
Eucalyptus, Blue Gum, contains cineol, pinene, limonene, cymene, phellandrene.
Eucalyptus, Broad-leaved Peppermint, contains piperitone, phellandrene, camphene, terpinene, thujune.
Eucalyptus, Lemon-Scented Eucalyptus, contains citronellal, citronellol, geranol, pinene.
Fennel seed oil (Foeniculum vulgare), Apiaceae.
contains anethole, limonene, phellandrene, pinene camphene, limonene, (fenchone in some varieties
Fenugreek oil (Trigonella foenum-graecum), Fabaceae.
Fir Needle oil, Silver Fir oil, contains santene, pinene, limonene, borneol, bornyl acetate, lauraldehyde.
Frankincense oil (Boswellia sacra), Bursuraceae.
(oleo gum resin), contains monoterpene hydrocarbons, e.g. pinene, dipentene, limonene, thujene, phellandrine, and also octanol.
Galangal oil (Alpinia) species, Zingiberaceae.
contains pinene, cineol, eugenol also sesquiterpenes.
Galbanum oil, contains pinene, edinol, cadinene, myrcene.
Galip nut oil (Canarium indicum), Burseraceae.
Gardenia oil, contains benzyl acetate, phenyl acetate, linalool, terpineol.
Garlic oil, distilled oil of garlic, (Allium sativum var. sativum), Amaryllidaceae.
Garlic, contains allicin, allylpropyl sidulfide, diallyl disulfide, citral, geraniol, linalool, phellandrene.
Geranium oil, contains citronellol, geraniol, linalool menthone, phellandrene, limonene.
Ginger oil (Zingiber officinale), Zingiberaceae.
contains gingerin, gingenol, gingerone, zingiberine, linalool, camphene, phellandrene, citral, cineol, borneol.
Ginkgo oil (Ginkgo biloba), Ginkgoaceae.
Ginseng oil (Panax) species, Araliaceae.
Goldenrod oil (Solidago canadensis), Asteraceae.
Golden seal oil (Hydrastis canadensis), Ranunculaceae.
Grapefruit oil, contains limonene, cadinene, neral, geraniol and fucocoumarins.
Guaiacwood oil, contains guaiol, bulnesol, bulnesene, guaiene (in blood tests).
Helichrysum oil contains nerol, neryl acetate, geraniol, pinene linalool, sesquiterpenes, furfurol, eugenol.
Henna tree oil, Henna oil (Lawsonia inermis), Lythraceae.
Hickory oil
Hops oil, contains humulene, myrcene, caryophyllene, farnesene.
Horseradish oil (Armoracia rusticana), Brassicaceae.
contains isothiocyanate and phenylethyl isothiocyanate from bruised plant.
Hyacinth, contains phenylethyl alcohol, benzaldehyde, benzoic acid.
Hyssop oil (Hyssopus officinalis), Lamiaceae.
contains pinocamphone, borneol, geranol, limonene, thujone, myrcene, caryophyllene.
Jasmine oil (Jasminum officinale), Oleaceae.
Java Oil contains geraniol, citronellal
Juniper oil (Juniperus communis), Cupressaceae.
Jaborandi oil
Juniper oil
Cistus ladaniferus, Cistaceae
contains pinene, camphene myrcene, phellandrene, limonene, cineol, borneol, nerol, geraniol
Laurel oil, Laurus nobilis oil
Lavender oil, True Lavender, (Lavendula angustifolia), Lamiaceae.
Lavandin
Ledum oil
Lemonoil, citron lemon (Citrus x limon), Rutaceae.
contains limonene, terpinene, pinene, linalool, geraniol
Lemongrass oil (Cymbopogon citratus), Poaceae
contains citral, myrcene linalool, geraniol, nerol, farnesol
Lime oil (Citrus x aurantifolia), Rutaceae.
Linaloe oil
Litsea cubeba oil
Lime balm oil (Melissa officinalis), Lamiaceae.
Lovage oil (Levisticum officinale), Apiaceae
Mandarin oil
Marigold oil (Calendula officinalis), Asteraceae
Marjoram oil (Origanum marjorana)
Mastic oil, (resin)
Melilotus oil
Melissa oil
Menthol, C10H20O
Mimosa oil
Mint oil (Mentha arvensis), Lamiaceae.
Mint, Spearmint, L-carvone
Mint (Mentha) species, Lamiaceae.
Moringa (Moringa oleifera), Moringaceae.
Mountain savory oil
Mountain tobacco oil (Arnica montana), Asteraceae.
Mugwort oil (Artemisia vulgaris), Asteraceae.
Mugwort (Artemisia vulgaris), Asteraceae
contains thujone cineol, pinene
Musk mallow oil (Abelmoschus moschatus), Malvaceae
Mustard (Brassica) species, Brassicaceae
Mustard oil (Brassica) species, Brassicaceae.
Myrrh oil (Commiphora myrrha), Burseraceae.
Myrrh (oleo gum resin), contains heerabolene, limonene, dipentene, pinene, eugenol also resins and gums
Myrtle (Myrtus communis), Myrtaceae
Narcissus
Myrtle oil (Myrtus communis), Myrtaceae.
Mint oil, Garden mint oil (Mentha sachalinensis), Lamiaceae.
Neem oil (Azadirachta indica), Meliaceae.
Neroli oil
Niaouli oil Melaleuca species, See: Melaleuca quinquenervia
Nutmeg oil ((Mystica fragrans), Lamiaceae
Oakmoss oil
Olive oil
Opopanax oil, Commiphora erytbraea, bisabol myrrh, Burseraceae. Bitter orange oil
Orange Blossom oil
Orange oil, Sweet Orange oil
Sweet orange oil (Citrus x sinensis)
Oregano oil (Origanum vulgare), Lamiaceae.
Orris oil (Iris florentina), Iridaceae.
Palosa
Palmarosa oil (Cymbopogon martinii), Poaceae
Parsley oil (Petroselinium crispum), Apiaceae.
Patchouli oil (Pogostemon patchouli), Lamiaceae.
Peppermint oil (Mentha X piperita), Lamiaceae
Perilla oil (Perilla frutescens), Lamiaceae.
Pennyroyal oil (Mentha pulegium), pennyroyal oil
Pepper oil (Piper nigrum), Piperaceae, Black Pepper
Peppermint oil
Petitgrain oil
Pimento oil
Pine oil
Pine, Dwarf Pine oil
Pine, Longleaf Pine oil
Pine, Scotch Pine oil
Ravensara oil
Red cedar oil
Roman chamomile oil
Rose buds (Rosa x centifolia), Rosaceae.
Rose, Cabbage Rose
Rose, Damask Rose
Rosehip oil, Rosa rubiginosa Rosemary, (Rosmarinus officinalis), Lamiaceae.
Rosewood oil
Rue oil (Ruta graveolens), Rutaceae
Sage oil (Salvia) species, Lamiaceae, Sandalwood oil
Santolina oil
Sassafras tree oil (Sassafras albidum), Lauraceae
Savine oil
Savory oil, Satureja species, Lamiaceae.
Schisandra oil
Spanish broom seed oil (Genet absolute) (Spartium junceum), Fabaceae
Spearmint oil
Spikenard oil (Nardostachys jatamansi), Caprifoliaceae.
Spruce oil
Star anise oil (Illicium verum), Illiciaceae.
Schinus Molle oil
Snakeroot oil
Spikenard oil
Spruce oil, Hemlock Spruce oil
Styrax oil, Levant Styrax oil
Tagetes oil
Tangerine oil
Tarragon oil (Artemisia dracunculus), Asteraceae.
Tea tree oil
Thyme oil (Thymus vulgaris), Lamiaceae.
Tsuga oil
Turmeric oil (Curcuma longa), Zingiberaceae.
Valerian oil (Valeriana officinalis), Caprifoliaceae.
Vetiver grass oil, khus oil, (Chrysopogon zizanioides), Poaceae.
Tansy oil (Tanacetum vulgare), Asteraceae
Tarragon oil (Artemisia dracunculus), Asteraceae, contains carvone terpenoid
Tea tree oil (Melaleuca alternifolia), Tea tree oil
Thuja oil (Thuja occidentalis), Cupressaceae
Thyme oil (Thymus vulgaris), Lamiaceae
Tonka
Tuberose oil (Polianthes tuberosa), Asparagaceae
Turmeric oil (Curcuma longa), Zingiberaceae
Turpentine tree oil (Syncarpia glomulifera), Myrtaceae
Valerian oil (Valeriana officinalis), Caprifoliaceae
Vanilla oil (Vanilla planifolia), Orchidaceae
Verbena oil (Verbena) species, Verbanaceae
Vetiver grass oil (Chrysopogon zizanioides), Poaceae
Violet oil (Viola odorata), Violaceae
Wariona oil
Western red cedar oil
Wintergreen oil (Gaultheria procumbens), Ericaceae
Wormseed oil (Dysphania ambrosioides), Amaranthaceae.
Wormwood oil (Artemisia absinthium), Asteraceae
Yarrow oil (Achillea millefolium), Asteraceae
Yew tree oil (Taxus baccata), Taxaceae.
Ylang ylang< oil/a> (Cananga odorata), Annonaceae.
Zeodary oil.

16.6.2 Fixed oils
Fixed oils (non-volatile oils, true oils, vegetable oils, aromatherapy carrier oils) are extracted
from seeds or nuts by different methods so they can be classed as "unrefined", "cold-pressed",
"expeller-pressed", "refined", and extracted using solvents, heat and/or steam.
1. Make a permanent greasy mark on paper
2. Cannot be distilled unchanged
3. Do not evaporate at room temperature, so are called "carrier oils",
but do not volatilize on heating without decomposition.
4. Are glycerides of fatty acids.
5. Harden on exposure to the air.
Fixed oils, base oils, carrier oils are oily, non-volatile, usually from the seed or nut.
They are called "fixed oils" because they have large molecules so do not evaporate like essential oils.
Carrier oils are mixtures of unsaturated and saturated fatty acids with some traces of vitamins, minerals and other trace plant constituents.

16.6.2a List of fixed oils
Aguaje oil (Buriti oil), Almond butter, Almond oil sweet
Andiroba oil, Apricot kernel oil, Arachis oil (peanut oil), Argane oil, Avocado butter, Avocado oil
Babassu nut oil, Baobab oil, Bayberry oil (Laurel seed oil)
Beeswax, Ben oil (Moringa oil), Bilberry seed oil, Blackcurrant seed oil
Bois de rose oil, rosewood oil (Aniba rosaeodora), Lauraceae, Borage oil, Brazil nut oil
Calendula oil, Calophyllum inophylum oil (Tamanu nut oil), Camelina sativa oil, Camellia oil
Candlenut oil (Aleurites moluccana), Canola oil (Brassica napus)16.14.5
Cape Chestnut oil, Capuacu butter, Caraway black oil, Carrot oil, Cashew kernel oil
Castor oil, chaulmoogra seed oil, Cherry kernel oil, Chia oil, Cocoa butter, Cocoa oil organic, Coconut oil
Cod liver oil, Coffee oil, Coffee butter, Corn oil corn oil (Zea mays), Cotton seed oil, cottonseed oil
(Gossypium), Crabwood oil (Andiroba seed), Cranberry seed oil, Cumin black oil
Dhupa butter, Echium seed oil, Emu oil from the emu bird, Evening primrose oil, Flax seed oil (Linseed oil)
Gold of pleasure oil (Camelina sativa), Grape seed oil, Groundnut oil (Peanut oil)
Hazelnut oil, Hempseed oil, Illipe butter, Jojoba oil, Kalahari oil, Karanja oil, Kemiri oil (Kukui nut oil)
Kiwifruit oil, Kokum butter (Garcinia indica), Krabwood oil, (Andiroba oil), Kukui nut oil, Lard (pig fat)
Laurel seed oil, Lettuce seed oil, Lingonberry oil, Linseed oil
Macadamia nut oil, Macadamia (Macadamia integrifolia), Proteaceae.
Mango kernel butter, Mango seed oil, Manketti nut oil
Margosa oil, Marigold oil (Calendula oil), Marula oil, Meadow foam seed oil, Mobola plum oil, Mongongo seed oil
Moringa oil, Mowrah butter, Mustard oil (Brassica campestris)
Neem oil, Azadirachta indica, Meliaceae, Ngali nut oil
Olives, Olea europaea , olive oil: 19.2.0
Ootanga oil (Watermelon oil), Orchid oil
Palm kernel oil (from kernel of oil palm, Elaeis guineensis)
Palm oil (from mesocarp of oil palm, Elaeis guineensis)
apaya seed oil, Parinari oil, Passionflower oil, Peach kernel oil, Peanut oil, Pecan nut oil, Perilla oil
Phulwara butter, Pistachio nut oil, Plum kernel oil, Pomegranate oil, Poppy seed oil, Pumpkin seed oil
Rapeseed oil (Canola oil), Raspberry seed oil, Rice bran oil, Rocket seed oil, Rosehip seed oil
Safflower seed oil (Carthamus tinctorius), Sal butter, Salmon oil, Sea buck thorn oil, Seaside plum oil (Ximenia oil)
Sesame seed oil, Sesame oil (Sesamum indicum), Shark liver oil, Shea oil, Shea butter, Soya bean oil, soybean oil (Glycine max)
Squalene oil (vegetable oil), St John's Wort oil, Strawberry seed oil, Sunflower oil (Helianthus annuus), Sunflower seed oil
Tamanu nut oil, Tucuma butter, Tung oil (Aleurites fordii), Urucum oil, Walnut oil, Watermelon seed oil
Wheat germ oil (cold pressed and refined), Ximenia oil (Seaside plum oil), Yangu oil (Cape Chestnut oil).

16.6.3 Vegetable oils
Vegetable oils, plant oils, are triglycerides extracted from plants by pressure or maceration that are usually liquid at room temperature.
Vegetable oils include cooking oils, e.g. canola oil, solid oils, e.g. cocoa butter, oils in paint, e.g. linseed oil, and industrial oils.
Pressed vegetable oils are extracted from the plants, usually seed, using a screw press or a ram press, which forces oil out
leaving seed cake.
Note that castor oil, linseed oil and tung oil are not edible.

16.6.3a List of vegetable oils
Almond oil
Aniline oil, oily, poisonous, liquid amine, used to make dyes, plastics, medicines
Castor oil, ricinoleic acid: 16.3.6.4
Clove oil, eugenol: 16.3.6.9
Coconut oil: 17.0
Eucalyptus oil
Evening primrose oil
Lavender oil
Lemon oil
Linseed oil
Neatsfoot oil
Oil of wintergreen, methyl salicylate
Pear oil, Prepare amyl acetate
Pennyroyal
Red oil, Oleic acid: 16.3.8.8
Salad oil
Tea tree oil
Tung oil
Vanilla oil
Vegetable oils, Prepare soap with vegetable oils: 12.12.2.