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(-)-α-Bisabolol

(-)-α-Bisabolol structure

(-)-α-Bisabolol 

structure
  • CAS No:

    23089-26-1

  • Formula:

    C15H26O

  • Chemical Name:

    (-)-α-Bisabolol

  • Synonyms:

    3-Cyclohexene-1-methanol,α,4-dimethyl-α-(4-methyl-3-penten-1-yl)-,(αS,1S)-;5-Hepten-2-ol,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-,(-)-;3-Cyclohexene-1-methanol,α,4-dimethyl-α-(4-methyl-3-pentenyl)-,[S-(R*,R*)]-;3-Cyclohexene-1-methanol,α,4-dimethyl-α-(4-methyl-3-pentenyl)-,(αS,1S)-;(αS,1S)-α,4-Dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol;(-)-α-Bisabolol;Levomenol;l-α-Bisabolol;α-Bisabolol,(-)-;(-)-(1′S,2S)-α-Bisabolol;α-(-)-Bisabolol;(-)-(4S,8S)-α-Bisabolol;Kamillosan;101467-45-2

  • Categories:

    Cosmetic Ingredient  >  Skin Conditioning

Description

Levomenol is a monocyclic sesquiterpene alcohol found in various plants and mainly in Matricaria chamomilla, which exerts antioxidant, anti-inflammatory, and anti-apoptotic activities. Levomenol has neuroprotective effects, can attenuate nociceptive behaviour and central sensitisation in a rodent model of trigeminal neuropathic pain[1][2].


Clear colourless liquid; Fruity nutty aroma with hints of coconut


(-)-alpha-Bisabolol is a sesquiterpenoid.|Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, (-)-alpha-Bisabolol is found in fats and oils. (-)-alpha-Bisabolol is isolated from essential oil of Matricaria chamomilla (German chamomile) (-)-alpha-Bisabolol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units.

(-)-α-Bisabolol Basic Attributes

222.37

222.37

245-423-3

24WE03BX2T

DTXSID4042094|DTXSID5045964

2906195000

Characteristics

20.2

5.07

clear to yellowish liquid

0.9211 g/cm3 @ Temp: 20 °C

153 °C @ Press: 12 Torr

135 °C

1.494

1.688 mg/L @ 25 °C (est)|Practically insoluble or insoluble in water|Slightly soluble (in ethanol)

-20°C

4E-05mmHg at 25°C

LD50 in male, female mice, rats (ml/kg): 15.2, 15.0, 14.9, 15.6 orally (Habersang)

D -55.7°; D20 -51.02° (Günther)

Safety Information

UN 3082 9 / PGIII

3

MJ9685000

P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, P501

H317

|Warning|H317 (34.72%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 228 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317 (83.52%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 278 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Levomenol has been known to elicit a number of potentially beneficial pharmacological effects, including anti-irritant, anti-inflammatory, and anti-microbial actions. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules

Levomenol is an anti-inflammatory and natural moisturizing agent that has been found to diminish the signs of photodamage, reduce pruritus, and ameliorate skin texture and elasticity.

The purpose of the present investigations was to study the cutaneous absorption of sesquiterpenic alcohol, the major active principle of chamomile. For these investigations 14C-labelled levomenol ((-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; (-)-alpha-bisabolol) was prepared by biochemical incorporation of [14C]-acetate into the molecule. 5 h after topical application of the radiolabelled substance onto nude mice half of the radioactivity was found in the skin. The other part was measured in tissue and organes. 90% of this radioactivity was analysed as intact levomenol.|To demonstrate the distribution of the substance in the skin a part of this tissue was cutted into horizontal slices by a cryotome. From the slices autoradiograms were produced. The densitometric measuration showed that there was a fast penetration of levomenol into the skin. 5 h after the topical application the substance was displaced from outermost to innermost areas. From these results a fast cutaneous absorption and a long therapeutical effect of the antiphlogistic and spasmolytic levomenol in the skin can be expected.

(+)-4-epi-alpha-bisabolol

(-)-α-Bisabolol Use and Manufacturing

3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-penten-1-yl)-, (.alpha.R,1R)-rel-: ACTIVE

Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]|Cosmetics -> Soothing

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:222.37
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:222.198365449
Monoisotopic Mass:222.198365449
Topological Polar Surface Area:20.2
Heavy Atom Count:16
Complexity:284
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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