Bisabolol

Source: Wikipedia, the free encyclopedia.
α-(−)-Bisabolol
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
3D model (
JSmol
)
5733954
ChEMBL
ChemSpider
ECHA InfoCard
 100.041.279 Edit this at Wikidata
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
  • (±): 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
  • (-): O[C@@](C)(CC\C=C(/C)C)[C@@H]1C/C=C(/C)CC1
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).

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol,

racemic mixture of the two, α-(±)-bisabolol. It is the terpenoid responsible for distinctive aroma of chamomile
flowers, and when isolated, its scent has also has been likened to apples, sugar and honey.

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 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.[4] Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties.[5][6] 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.[4][7]

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. ISBN 3-527-30673-0
    .
  4. ^ a b Loyd V. Allen Jr (2013). Tretinoin 0.5 mg/g and α-Bisabolol 1 mg/g Gel and discussion on its use.
  5. S2CID 12654188
    .
  6. S2CID 52282324
    .
  7. S2CID 95169851
    .
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