Bisabolol
Names | |
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Preferred IUPAC name
(2S)-6-Methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol | |
Other names
Levomenol
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Identifiers | |
3D model (JSmol)
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5733954 | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.041.279 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H26O | |
Molar mass | 222.372 g·mol−1 |
Density | 0.92 g cm−3 |
Boiling point | 153 °C (307 °F; 426 K) at 12 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol,[1] 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.[2] It is poorly soluble in water and glycerin, but soluble in ethanol.[3] The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol.
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 perceived skin healing properties. Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties.[4][5] Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules.[6]
A structurally related compound known as β-bisabolol (CAS registry number [15352-77-9]) differs only in the position of the tertiary alcohol functional group.
References[]
- ^ Rohstoff-Lexikon Bisabolol Archived February 20, 2008, at the Wayback Machine
- ^ Bisabolol (in english) Archived October 10, 2007, at the Wayback Machine
- ^ M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.
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: CS1 maint: uses authors parameter (link) - ^ Rocha, Nayrton Flávio Moura; Rios, Emiliano Ricardo Vasconcelos; Carvalho, Alyne Mara Rodrigues; Cerqueira, Gilberto Santos; Lopes, Amanda de Araújo; Leal, Luzia Kalyne Almeida Moreira; Dias, Marília Leite; de Sousa, Damião Pergentino; de Sousa, Francisca Cléa Florenço (December 2011). "Anti-nociceptive and anti-inflammatory activities of (-)-α-bisabolol in rodents". Naunyn-Schmiedeberg's Archives of Pharmacology. 384 (6): 525–533. doi:10.1007/s00210-011-0679-x. ISSN 1432-1912. PMID 21870032.
- ^ Rodrigues, Fabíola Fernandes Galvão; Colares, Aracélio Viana; Nonato, Carla de Fatima Alves; Galvão-Rodrigues, Fabío Fernandes; Mota, Magaly Lima; Moraes Braga, Maria Flaviana Bezerra; Costa, José Galberto Martins da (December 2018). "In vitro antimicrobial activity of the essential oil from Vanillosmopsis arborea Barker (Asteraceae) and its major constituent, α-bisabolol". Microbial Pathogenesis. 125: 144–149. doi:10.1016/j.micpath.2018.09.024.
- ^ Kamatou, Guy P. P.; Viljoen, Alvaro M. (2010). "A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils". Journal of the American Oil Chemists' Society. 87 (1): 1–7. doi:10.1007/s11746-009-1483-3. S2CID 95169851.
- Tertiary alcohols
- Perfume ingredients
- Cosmetics chemicals
- Sesquiterpenes
- Cyclohexenes