Bisabolol

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] 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.^[3] 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.

Quick facts Names, Identifiers ...

α-(−)-Bisabolol

Names
Preferred IUPAC name (2S)-6-Methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Other names Levomenol
Identifiers
CAS Number	(-): 23089-26-1 (±): 515-69-5
3D model (JSmol)	(-): Interactive image
Beilstein Reference	5733954
ChEMBL	(-): ChEMBL1096927
ChemSpider	(-): 390796
ECHA InfoCard	100.041.279
PubChem CID	(-): 442343 (±): 10586
UNII	(-): 24WE03BX2T (±): 36HQN158VC
CompTox Dashboard (EPA)	(-): DTXSID4042094
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	222.372 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

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Bisabolol has a weak sweet floral aroma described as fruity, nutty, and coconut,^[4] 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.^[5] Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties.^[6][7] 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.^[5][8]

The structurally related compound, β-bisabolol (15352-77-9 ), differs in the positioning of the tertiary alcohol functional group.

• 
  (−)-α-Bisabolol
• 
  β-Bisabolol