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 combinations. Biochemical modifications s ...

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 ...

from German chamomile (''

Matricaria recutita ''Matricaria'' is a genus of flowering plants in the chamomile tribe within the sunflower family. Some of the species have the common name of "mayweed", but this name also refers to plants not in this genus. Description Their many-branched ...

'') and '' Myoporum crassifolium''. High concentrations of bisabolol can also be found in certain

medicinal cannabis Medical cannabis, medicinal cannabis or medical marijuana (MMJ) refers to Cannabis (drug), cannabis products and cannabinoid, cannabinoid molecules that are prescription drug, prescribed by physicians for their patients. The use of cannabi ...

cultivars. It is poorly soluble in water and

glycerine Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in ...

, but soluble in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

. The

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

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

racemic In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) 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 r ...

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

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

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 chamomilla'' and '' Chamaemelum nobile'', are commo ...

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 acute promyelocytic leukemia, ...

as a topical treatment for

acne Acne ( ), also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, ...

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

References

Tertiary alcohols Perfume ingredients Cosmetics chemicals Sesquiterpenes Cyclohexenes