Structure via PubChem · Public domain (PubChem)
levomenol
Sign in to saveAlso 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
via Wikidata · CC0
~2 min read
Article
1 sectionsContents
- 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.
Available in 19 languages
- Français
- Deutsch
- 日本語
- Português
- Italiano
- العربية
- azb
- Bahasa Indonesia
- Czech
- Finnish
- Macedonian
- Malay
- Nederlands
- Serbian
- Serbian (Latin)
- Türkçe
- Urdu
- فارسی
via Wikidata sitelinks · CC0