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Bisabolol

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α-(-)-Bisabolol
Stereo structural formula of α-(-)-Bisabolol
Names
Preferred IUPAC name
6-Methyl-2-(4-methylcyclohex-3-enyl)hept-5-en-2-ol
Systematic IUPAC name
6-Methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
Other names
α-Bisabolol
Levomenol
Identifiers
3D model (JSmol)
5733954
ChemSpider
ECHA InfoCard 100.041.279 Edit this at Wikidata
EC Number
  • 208-205-9
MeSH Bisabolol
RTECS number
  • MJ9685000
UNII
  • InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3
    Key: RGZSQWQPBWRIAQ-UHFFFAOYSA-N
  • InChI=1/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
    Key: RGZSQWQPBWRIAQ-CABCVRREBV
  • CC(C)=CCCC(C)(O)C1CCC(C)=CC1
  • O[C](C)(CC\C=C(/C)C)[CH]1C/C=C(/C)CC1
Properties
C15H26O
Molar mass 222.372 g·mol−1
Density 0.92 g/cm3
Boiling point 153 °C at 12 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 grassifolium[2]. It is almost insoluble in water and glycerin, but well 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.

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. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules.

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.

β-Bisabolol