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levomenol

Structure via PubChem · Public domain (PubChem)

EntityQ179896· pop 20· linked from 186 articles

Also known as bisabolol, alpha-bisabolol, Bisabolol, α-(−)-bisabolol, Kamillosan, alpha-(−)-bisabolol, (−)-alpha-Bisabolol

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (Matricaria recutita) and Myoporum crassifolium. High concentrations of bisabolol can also be found in certain medicinal cannabis cultivars. It is poorly soluble in water and glycerine, but soluble in ethanol. The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol. It is the terpenoi

Chemical data

Formula
C15H26O
Molecular weight
222.37 g/mol
IUPAC name
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
SMILES
CC1=CC[C@H](CC1)[C@](C)(CCC=C(C)C)O
InChIKey
RGZSQWQPBWRIAQ-CABCVRRESA-N
XLogP
3.8
Polar surface area
20.2 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Wikidata facts

Mass
222.198
Show 5 more facts
chemical formula
C₁₅H₂₆O
Commons category
Bisabolol
canonical SMILES
CC1=CCC(CC1)C(C)(CCC=C(C)C)O
isomeric SMILES
CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1
NCI Thesaurus ID
C80904
Sources (3)

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Contents
  • References

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (Matricaria recutita) and Myoporum crassifolium. High concentrations of bisabolol can also be found in certain medicinal cannabis cultivars. It is poorly soluble in water and glycerine, but soluble in ethanol. The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol. It is the terpenoid responsible for the distinctive aroma of chamomile flowers, and when isolated, its scent has also been likened to apples, sugar and honey.

Bisabolol has a weak sweet floral aroma described as fruity, nutty, and coconut, 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 as a topical treatment for acne. 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.

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