-Pinene

is an organic compound of the terpene class, one of two isomers of pinene.[1] It is an alkene
and it contains a reactive four-membered ring. It is found in the oils of many species of many
coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus
officinalis).[2] Both enantiomers are known in nature; (1S,5S)- or ()--pinene is more common
in European pines, whereas the (1R,5R)- or (+)--isomer is more common in North America. The
racemic mixture is present in some oils such as eucalyptus oil.
a-pinene is a natural essential oil with special chemial activity, is the material of synthetic
camphor, compound essence, synthetic resin, pharmaceutical and other organic synthesis
industries.
In the atmosphere alpha-pinene undergoes reactions with ozone, the OH radical or the NO3
radical,[6] leading to low-volatility species which partly condense on existing aerosols, thereby
generating secondary organic aerosols
Sabinene
Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated
from the essential oils of a variety of plants including holm oak (Quercus ilex) and Norway
spruce (Picea abies). It has a strained ring system with cyclopentane ring fused to a cyclopropane
ring.
Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper and
is a major constituent of carrot seed oil. It also occurs in tea tree oil at a low concentration. It is
also present in the essential oil obtained from nutmeg.[2]
Myrcene
Myrcene, or -myrcene, is an olefinic natural organic compound. It is classified as a
hydrocarbon, more precisely as a monoterpene. Terpenes are dimers of isoprene, and myrcene is
one of the most important. It is a component of the essential oil of several plants including bay,
ylang-ylang, wild thyme, and hops.[3][4] It is produced mainly semi-synthetically from myrcia,
from which it gets its name. It is a key intermediate in the production of several fragrances. Myrcene is the name for the structural isomer 2-methyl-6-methylene-1,7-octadiene, which is not
found in nature and is little used.[5]
Use in fragrance industry
Myrcene is an important intermediate used in the perfumery industry. It has pleasant odor, but is
rarely used directly. It is also unstable in air, tending to polymerize. Samples are stabilized by the
addition of alkylphenols or tocopherol. It is thus more highly valued as an intermediate for the
preparation of flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal,
geraniol, nerol, and linalool. Treatment of myrcene with hydrogen chloride gives geranyl
chloride, neryl chloride, and linalyl chloride. Treatment of these compounds with acetate gives
geranyl acetate, neryl acetate, and linalyl acetate, respectively. These esters are then hydrolyzed
to the corresponding alcohols. Myrcene is also converted to myrcenol, another fragrance found
in lavender, via uncatalyzed hydroamination of the 1,3-diene followed by hydrolysis and Pdcatalyzed removal of the amine.

As 1,3-dienes, both myrcene and mycenol undergo Diels-Alder reactions with several
dienophiles such as acrolein to give cyclohexene derivatives that are also useful fragrances.[2]
[edit]
Partial list of the plants that contain myrcene
As mentioned above, many plants contain myrcene, sometimes in very large amounts.[5]
Houttuynia
Mangoes
Hops
Lemon grass
West Indian Bay Tree
Verbena
Mercia
Limonene
Limonene is a colourless liquid hydrocarbon classified as a cyclic terpene. The more common D
isomer possesses a strong smell of oranges.[1] It is used in chemical synthesis as a precursor to
carvone and as a renewably-based solvent in cleaning products.
Limonene takes its name from the lemon, as the rind of the lemon, like other citrus fruits,
contains considerable amounts of this compound, which contributes to their odor. Limonene is a
chiral molecule, and biological sources produce one enantiomer: the principal industrial source,
citrus fruit, contains D-limonene ((+)-limonene), which is the (R)-enantiomer (CAS number
5989-27-5, EINECS number 227-813-5). Racemic limonene is known as dipentene.[2] DLimonene is obtained commercially from citrus fruits through two primary methods: centrifugal
separation or steam distillation.
The most widely practiced conversion of limonene is to carvone. The three step reaction begins
with the regioselective addition of nitrosyl chloride across the trisubstituted double bond. This
species is then converted to the oxime with base, and the hydroxylamine is removed to give the
ketone-containing carvone.[1]
Limonene is common in cosmetic products. As the main odor constituent of citrus (plant family
Rutaceae), D-limonene is used in food manufacturing and some medicines, e.g. as a flavoring to
mask the bitter taste of alkaloids, and as a fragrant in perfumery; it is also used as botanical
insecticide.,[6] particularly the (R)-(+)-enantiomer is most active as an insecticide. It is added to
cleaning products such as hand cleansers to give a lemon-orange fragrance (see orange oil). In
contrast, L-limonene has a piney, turpentine-like odor.
In natural and alternative medicine, D-limonene is marketed to relieve gastroesophageal reflux
disease and heartburn.[7]
Limonene is increasingly being used as a solvent for cleaning purposes, such as the removal of
oil from machine parts, as it is produced from a renewable source (citrus oil, as a byproduct of
orange juice manufacture). It also serves as a paint stripper when applied to painted wood and is

also useful as a fragrant alternative to turpentine. Limonene is also used as a solvent in some
model airplane glues. All-natural commercial air fresheners, with air propellants, containing
limonene are used by philatelists to remove self-adhesive postage stamps from envelope
paper.[8]
As it is combustible, limonene has also been considered as a biofuel.[9]
Limonene can be used to dissolve polystyrene, and is a more ecologically friendly substitute for
acetone.[citation needed]
In preparing tissues for histology or histopathology, D-limonene is often used as a less toxic
substitute for xylene when clearing dehydrated specimens. Clearing agents are liquids miscible
with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens
are embedded to facilitate cutting
Safety
Limonene and its oxidation products are skin and respiratory irritants, and limonene-1,2-oxide
(formed by aerial oxidation) is a known skin sensitizer. Most reported cases of irritation have
involved long-term industrial exposure to the pure compound, e.g. during degreasing or the
preparation of paints. However a study of patients presenting dermatitis showed that 3% were
sensitized to limonene.[13]
Although high doses have been shown to cause renal cancer in male rats,[14] limonene is
considered by some researchers to be a potential chemopreventive agent [15] with value as a
dietary anti-cancer tool in humans.[16] There is no evidence for carcinogenicity or genotoxicity
in humans. The IARC classifies D-limonene as a Group 3 carcinogen: not classifiable as to its
carcinogenicity to humans.[13][17]
No information is available on the health effects of inhalation exposure to D-limonene in
humans,[dubious discuss] and no long-term inhalation studies have been conducted in
laboratory animals.[citation needed]
D-Limonene is biodegradable, but due to its low flash point, it must be treated as hazardous
waste for disposal.[citation needed]

Linalool
Linalool ( /lnl.l/) is a naturally occurring terpene alcohol chemical found in many flowers
and spice plants with many commercial applications, the majority of which are based on its
pleasant scent (floral, with a touch of spiciness). It has other names such as -linalool, linalyl
alcohol, linaloyl oxide, p-linalool, allo-ocimenol, and 2,6-dimethyl-2,7-octadien-6-ol.
Over 200 species of plants produce linalool, mainly from the families Lamiaceae (mints, scented
herbs), Lauraceae (laurels, cinnamon, rosewood), and Rutaceae (citrus fruits), but also birch trees
and other plants, from tropical to boreal climate zones. It has also been found in some fungi.
Linalool is used as a scent in 6080% of perfumed hygiene products and cleaning agents
including soaps, detergents, shampoos, and lotions.[1] It is also used as a chemical intermediate.
One common downstream product of linalool is Vitamin E. In addition, linalool is used by pest
professionals as a flea and cockroach insecticide.
Linalool is used in some mosquito repellent products, however the EPA notes that: "A
preliminary screen of labels for products containing Linalool (as the sole active ingredient)
indicates that efficacy data on file with the Agency may not support certain claims to repel
mosquitos."[2]
Akio Nakamura together with colleagues from the University of Tokyo and T. Hasegawa Co.,
Ltd in Kawasaki, Japan, claim to have demonstrated that inhaling linalool can reduce stress in
lab rats. In a study published in The Journal of Agriculture and Food Chemistry,[3] they exposed
the animals to stressful conditions and found that those inhaling linalool saw their stress-elevated
levels of neutrophils and lymphocytes fall to near-normal levels compared with the controls.
Inhaling linalool also reduced the activity of more than 100 genes that "go into overdrive" in
stressful situations. The findings could form the basis of new blood tests for identifying
fragrances that can soothe stress, the researchers claim.[4]
Linalool gradually breaks down when in contact with oxygen, forming an oxidized by-product
that may cause allergic reactions such as eczema in susceptible individuals. Between 57% of
patients undergoing patch testing in Sweden were found to be allergic to the oxidized form of
linalool.[1] Ways to minimize exposure include not buying large bottles of perfumed hygiene
products, and replacing the lid after each use.
Citronellal
Citronellal or rhodinal or 3,7-dimethyloct-6-en-1-al (C10H18O) is a monoterpenoid, the main
component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive
lemon scent.
Citronellal is a major isolate in distilled oils from the plants Cymbopogon,[2] lemon-scented
gum, and lemon-scented teatree.
Citronellal has insect repellent properties, and research shows high repellent effectiveness
against mosquitoes.[3] Research shows that citronellal has strong antifungal qualities.[4]

Citral
Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either of, or a mixture of, a pair of
terpenoids with the molecular formula C10H16O. The two compounds are double bond isomers.
The E-isomer is known as geranial or citral A. The Z-isomer is known as neral or citral B.
Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata
(90%), Litsea cubeba (70-85%), lemongrass (65-85%), lemon tea-tree (70-80%), Ocimum
gratissimum (66.5%), Lindera citriodora (about 65%), Calypranthes parriculata (about 62%),
petitgrain (36%), lemon verbena (30-35%), lemon ironbark (26%), lemon balm (11%), lime (69%), lemon (2-5%), and orange.[2][3][4]
Geranial has a strong lemon odor. Neral's lemon odor is less intense, but sweeter. Citral is
therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a
flavor and for fortifying lemon oil. It also has strong antimicrobial qualities,[5] and pheromonal
effects in insects.[6][7]
Citral is used in the synthesis of vitamin A, ionone, and methylionone, and to mask the smell of
smoke.
Camphene
Camphene is bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common
organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor
constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil,
neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more
common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive
for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness.
Eucalyptol
is a natural organic compound which is a colorless liquid. It is a cyclic ether and a
monoterpenoid.
Eucalyptol is also known by a variety of synonyms: 1,8-cineol, 1,8-cineole, limonene oxide,
cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
In 1870, F.S. Cloez identified and ascribed the name eucalyptol to the dominant portion of
Eucalyptus globulus oil.[1] Eucalyptus oil, the generic collective name for oils from the
Eucalyptus genus, should not be confused with the chemical compound eucalyptol.
Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product
Eucalyptus oil,[1] hence the common name of the compound. It is also found in camphor laurel,
bay leaves, tea tree, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant

foliage. Eucalyptol with a purity from 99.6 to 99.8 percent can be obtained in large quantities by
fractional distillation of eucalyptus oil.
Although it can be used internally as a flavoring and medicine ingredient at very low doses,
typical of many essential oils (volatile oils), eucalyptol is toxic if ingested at higher than normal
doses.[2]
Uses
[edit]
Flavoring and fragrance
Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and
cosmetics. Cineole based eucalyptus oil is used as a flavouring at low levels (0.002%) in various
products, including baked goods, confectionery, meat products and beverages.[3] In a 1994
report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives
to cigarettes. It is claimed that it is added to improve the flavor.
[edit]
Medicinal
Eucalyptol suppository, for the treatment of some respiratory ailments
Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant.
Primary Research:
In a 2003 study eucalyptol was found to control airway mucus hypersecretion and asthma, after
in a previous study the authors found eucalyptol to suppress arachidonic acid metabolism and
cytokine production in human monocytes.[4][5]
In a 2004 study it was found to inhibit cytokine production in cultured human lymphocytes and
monocytes.[6]
In a 2004 study Eucalyptol was found to be an effective treatment for nonpurulent rhinosinusitis.
Treated subjects experienced less headache on bending, frontal headache, sensitivity of pressure
points of trigeminal nerve, impairment of general condition, nasal obstruction, and rhinological
secretion. Side effects from treatment were minimal.[7]
A 2000 study found Eucalyptol to reduce inflammation and pain when applied topically.[8]
In a 2002 study it was found to kill leukaemia cells of two cultured human leukemia cell lines,
but not cells of a human stomach cancer cell line in vitro.[9]
[edit]
Insecticide and repellent
Eucalyptol is used as an insecticide and insect repellent.[10][11]
Conversely, eucalyptol is one of many compounds that is attractive to males of various species of
orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used
as bait to attract and collect these bees for study.[12]

The terpinenes
are a group of isomeric hydrocarbons that are classified as terpenes. They each have the same
molecular formula and carbon framework, but they differ in the position of carbon-carbon double
bonds. -Terpinene has been isolated from cardamom and marjoram oils, and from other natural
sources. -Terpinene has no known natural source, but has been prepared synthetically from
sabinene. -Terpinene and -terpinene (also known as terpinolene) are natural and have been
isolated from a variety of plant sources
Cariophyllene
Caryophyllene ( /kri.flin/), or ()--caryophyllene, is a natural bicyclic sesquiterpene that
is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of
Syzygium aromaticum (cloves),[1] the essential oil of hemp Cannabis sativa,[2] rosemary
Rosmarinus oficinalis,[3] and hops.[4] It is usually found as a mixture with isocaryophyllene (the
cis double bond isomer) and -humulene (obsolete name: -caryophyllene), a ring-opened
isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature.
Caryophyllene is one of the chemical compounds that contributes to the spiciness of black
pepper. In a study conducted by Jrg Gertsch et al. from the Swiss Federal Institute of
Technology (ETH Zurich), beta-caryophyllene was shown to selectively bind to the cannabinoid
receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in
mice.[2] Since the widespread plant natural product beta-caryophyllene is an FDA approved
food additive and ingested daily with food it is the first dietary cannabinoid. Whether this
compound is able to modulate inflammatory processes in humans via the endocannabinoid
system is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid
receptor type-1 (CB1) and therefore does not exert psychomimetic effects.
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic
demonstrations of the possibilities of synthetic organic chemistry at the time.[5]