Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic

sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modific ...

alcohol. It is a colorless viscous oil that is the primary constituent of the

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

from

German chamomile ''Matricaria chamomilla'' (synonym: ''Matricaria recutita''), commonly known as chamomile (also spelled camomile), German chamomile, Hungarian chamomile (kamilla), wild chamomile, blue chamomile, or scented mayweed, is an annual plant of the com ...

(''

Matricaria recutita ''Matricaria chamomilla'' (synonym: ''Matricaria recutita''), commonly known as chamomile (also spelled camomile), German chamomile, Hungarian chamomile (kamilla), wild chamomile, blue chamomile, or scented mayweed, is an annual plant of the com ...

'') and ''

Myoporum crassifolium ''Myoporum crassifolium'' is a plant in the figwort family, Scrophulariaceae. It is a shrub or small tree with thick, fleshy leaves and small groups of white flowers spotted with pink or purple. It is endemic to New Caledonia, Vanuatu and the Loy ...

''. High concentrations of bisabolol can also be found in certain

medicinal cannabis Medical cannabis, or medical marijuana (MMJ), is cannabis and cannabinoids that are prescribed by physicians for their patients. The use of cannabis as medicine has not been rigorously tested due to production and governmental restrictions ...

cultivars. It is poorly soluble in water and

glycerine Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids know ...

, but soluble in

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...

. The

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a

racemic In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

mixture of the two, α-(±)-bisabolol. It is the

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...

responsible for distinctive aroma of

chamomile Chamomile (American English) or camomile (British English; see spelling differences) ( or ) is the common name for several plants of the family Asteraceae. Two of the species, ''Matricaria recutita'' and ''Anthemis nobilis'', are commonly us ...

flowers, and when isolated, its scent has also has been likened to apples, sugar and honey. Bisabolol has a weak sweet floral aroma and is used in various fragrances. It has also been used for hundreds of years in cosmetics because of its skin healing properties including reducing wrinkles, skin toughness and repairing sun-damaged skin, and more recently it has been compounded with

tretinoin Tretinoin, also known as all-''trans'' retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia. For acne, it is applied to the skin as a cream, gel or ointment. For leukemia, it is taken by mouth f ...

as a topical treatment for

acne Acne, also known as ''acne vulgaris'', is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and ...

. Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules and has found use as a

penetration enhancer Penetration may refer to: Science and technology * Passage through a partition or wall by a wire, cable, or other electrically conductive object * Penetration (firestop), an opening in a wall or floor assembly required to have a fire-resistance r ...

: an agent used in topical formulations, increasing the substances propensity for absorption beneath the

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different ...

. A structurally related compound known as β-bisabolol (

CAS registry number A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...

5352-77-9 differs only in the position of the tertiary alcohol functional group. {{clear

References

Tertiary alcohols Perfume ingredients Cosmetics chemicals Sesquiterpenes Cyclohexenes