Ylang Ylang

1. Ylang ylang means "flowers of flowers."

A variety, Cangana odorata macrophylla (Cannagium odoratum macrophylla) yields Cananga oil,
also used in the manufacture of cosmetics and soap, flavoring of foods as gelatins and puddings.
Ilang-ilang is a medium-sized tree growing 10 to 30 meters in height, with pendulous branches,
with drooping, leafy twigs. Flowers are fragrant, axillary, in umbellate hanging clusters, with
three sepals and six petals, twisted when young and drooping when mature. Leaves are dark
green, up to 20 centimeters in length, alternate, simple, entire. Fruit is black in color, 1.5 to 2
centimeters in length, in axillary clusters, fleshy and olive-like, with six to 12 seeds in each fruit.
Originating in the Philippines, ylang ylang means flower of flowers or fragrance of all
fragrances. This fragrance is traditionally used in aromatherapy to sharpen the senses and to
temper depression, fear, anger, and jealousy. For these reasons, and also because of its reputation
as an aphrodisiac, the flowers are spread on the beds of the newly married in Indonesia.
Modern aromatherapists find the scent strongly sedating, easily sending the most reluctant
sleeper off to dreamland. Science, on the other hand, regards ylang ylang essential oil more as a
mental stimulant.
Technical Details
Botanical Name

Cananga odorata

Family

Annonaceae

Part Used

Flowers

Origin

India

Mode of Extraction

Steam Distiled

Main Constituents

Geraniol, linalool, p-cresol methyl ether, linalyl acetate

Description

Clear Transparent Liquid

Appearence

Colourless to pale yellow liquid

Organoleptic properties

Highly fragrant oil

Specific Gravity at 20 C

0.930-0.950

Solubility

Insoluble in water; soluble in organic solvents

2. The major active constituents of ylang ylang essential oil are benzyl acetate (mild jasmine,
fruity fragrance), linalool (antifungal, antiseptic, sedative, used in synthesis of vitamin A) pcresyl methyl ether (odor) and methyl benzoate (fragrance). Other constituents that contribute to
the fragrance of ylang ylang are p-cresol, eugenol, isoeugenol, geranyl acetate and benzyl
salicylate. The oil also contains farnesyl acetate (normalizes sebaceous glands) and other
sesquiterpenes and their oxygenated derivatives.
Linalool has been the subject of numerous studies investigating its anxiolytic (anti-stress)
effects. Inhalation of Linalool, extracted from natural essential oils, leads to decreased aggressive
behavior, lessens stress response, and improves sleep.

3.

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 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.

IUPAC name
3,7-dimethylocta-1,6-dien-3-ol
Enantiomers
Linalool has a stereogenic center at C3 and therefore there are two stereoisomers: (R)-()-linalool
is also known as licareol and (S)-(+)-linalool is also known as coriandrol.

(S)-(+)-linalool (left) and (R)-()-linalool (right)

Both enantiomeric forms are found in nature: (S)-linalool is found, for example, as a major
constituent of the essential oils of coriander (Coriandrum sativum L. family Apiaceae) seed,
palmarosa [Cymbopogon martinii var martinii (Roxb.) Wats., family Poaceae], and sweet orange
(Citrus sinensis Osbeck, family Rutaceae) flowers. (R)-linalool is present in lavender
(Lavandula officinalis Chaix, family Lamiaceae), bay laurel (Laurus nobilis, family Lauraceae),
and sweet basil (Ocimum basilicum, family Lamiaceae), among others.
Each enantiomer evokes different neural responses in humans, and therefore are classified as
possessing distinct scents. (S)-(+)-Linalool is perceived as sweet, floral, petitgrain-like (odor
threshold 7.4 ppb) and the (R)-form as more woody and lavender-like (odor threshold 0.8 ppb).

4. a) Extraction of linalool is based on fractionation distillation of essential oils of mainly bois

de rose, shiu (camphor) or coriander.
b) Partial synthesis starts either from alpha- or beta-pinene (CAS 80-56-8 & 127-91-3). alphaPinene is hydrated selectively to cis-pinane (6876-13-7) and subsequently oxidised to cis/trans
(ca 75%/25%) pinane hydroperoxide (28324-52-9), which is in turn reduced to pinanols (various
CAS numbers) and the latter finally pyrolysed to the respective linalools.
c) Total chemical synthesis of linalool is by way of 2-methyl-2-hepten-6-one (110-93-0). It may
start from addition of acetylene (74-86-2) to acetone (67-64-1) resulting in 3-methyl-1-butyn-3ol (115-19-5), which is hydrated in the presence of a palladium catalyst to 3-methyl-1-buten-3-ol
(115-18-4), which is reacted with either diketene or acetic acid ester to the acetoacetate and the
latter thermally reacted to 2-methyl-2-hepten-6-one. Alternatively, 3-methyl-1-buten-3-ol is
reacted with isopropenyl methyl ether (116-11-0) to 2-methyl-2-hepten-6-one. In a third
synthetic pathway, isoprene hydrochloride is reacted with acetone in the presence of an alkaline
condensing agent or in the presence of organic bases as catalysts to 2-methyl-2-hepten-6-one. 2Methyl-2-hepten-6-one is then reacted with acetylene to dehydrolinalool (CAS 29171-20-8),
which is finally partially hydrated using hydrogen gas on a catalyst of platinum on activated
charcoal. Subsequently the product linalool is purified through vacuum distillation.