Bisabolol

α-(−)-Bisabolol

Names
IUPAC name 6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
Other names Levomenol
Identifiers
CAS Number	23089-26-1
3D model (Jmol)	Interactive image
Beilstein Reference	5733954
ChEMBL	ChEMBL1096927
ChemSpider	390796
ECHA InfoCard	100.041.279
PubChem	10586
UNII	24WE03BX2T
InChI 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 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
SMILES O[C@@](C)(CC\C=C(/C)C)[C@@H]1C/C=C(/C)CC1
Properties
Chemical formula	C15H26O
Molar mass	222.37 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 almost insoluble in water and glycerin, but very 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.^[3]

α-bisabolol has recently been shown to induce apoptosis in models of leukemia.^[4]

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

References

1. ↑ Rohstoff-Lexikon Bisabolol Archived February 20, 2008, at the Wayback Machine.
2. ↑ Bisabolol (in english) Archived October 10, 2007, at the Wayback Machine.
3. ↑ J Am Oil Chem Soc (2010) 87;1-7.
4. ↑ Cavalieri, E; Rigo, A; Bonifacio, M; Carcereri de Prati, A; Guardalben, E; Bergamini, C; Fato, R; Pizzolo, G; Suzuki, H; Vinante, F (Apr 21, 2011). "Pro-apoptotic activity of α-bisabolol in preclinical models of primary human acute leukemia cells.". Journal of translational medicine. 9: 45. doi:10.1186/1479-5876-9-45. PMC 3112094. PMID 21510902.