alpha-Bisabolol

alpha-Bisabolol
Compound Structure:
Synonyms: alpha-Bisabolol;Bisabolol;(+)-alpha-Bisabolol;515-69-5;23178-88-3;D-alpha-Bisabolol;(2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol;(+)-(1'R,2R)-alpha-Bisabolol;Dragosantol;Camilol;Hydagen B
Compound ID: NMPC-575
PubChem ID:

1549992

Molecular Formula: C15H26O
Canonical SMILES: CC1=CCC(CC1)C(C)(CCC=C(C)C)O
InChIKey: RGZSQWQPBWRIAQ-LSDHHAIUSA-N
About the compound:

Bisabolol, also known as α-(−)-bisabolol or levomenol, is a natural monocyclic sesquiterpene alcohol. It is commonly found in various organisms, including Eupatorium altissimum, Psidium guajava, German chamomile (Matricaria recutita), and Myoporum crassifolium. Bisabolol is known for its unique properties and uses in cosmetics and skincare. Chemical Structure: Bisabolol is a colorless viscous oil and belongs to the sesquiterpene class of compounds. It can exist in several enantiomeric forms, with α-(−)-bisabolol being the most common. It is poorly soluble in water and glycerine but soluble in ethanol.

Natural Sources: The primary natural source of bisabolol is German chamomile, where it is the major constituent of the essential oil. It is also present in some medicinal cannabis cultivars and other plant species.

Aroma: Bisabolol contributes to the distinctive aroma of chamomile flowers. Its scent is often described as having a weak sweet floral aroma, with notes of apples, sugar, and honey.

Cosmetic and Skincare Uses: Bisabolol has been used in cosmetics for centuries due to its skin-healing properties. It is known for its ability to reduce wrinkles, improve skin toughness, and repair sun-damaged skin. It is also used in topical treatments for acne when compounded with tretinoin. Bisabolol is valued for its anti-irritant, anti-inflammatory, and antimicrobial properties.

Penetration Enhancer: Bisabolol is used as a penetration enhancer in topical formulations. It helps increase the absorption of certain molecules beneath the skin, making it a valuable ingredient in skincare products.

Structural Variant: There is a structurally related compound called β-bisabolol, which differs only in the position of the tertiary alcohol functional group.

GHS Hazard Statements

H317 (83.58%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H411 (98.91%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

222.37 g/mol

XLogP3-AA

3.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

4

Exact Mass

222.198365449 g/mol

Monoisotopic Mass

222.198365449 g/mol

Topological Polar Surface Area

20.2²

Heavy Atom Count

16

Formal Charge

0

Complexity

284

Isotope Atom Count

0

Defined Atom Stereocenter Count

2

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Physical Description

Clear colourless liquid; Fruity nutty aroma with hints of coconut

Density

0.922-0.931

Solubility 

Practically insoluble or insoluble in water

Source: PubChem

Source Species: Monodora tenuifolia
Taxodium distichum
Download SDF