(-)-alpha-bisabolol
Synonym(s):(−)-α-Bisabolol;(−)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol;(-)-alpha-Bisabolol;(3S,6S)-Tetrahydro-2,2,6-trimethyl-6-[(1S)-4-methyl-3-cyclohexen-1-yl]-2H-pyran-3-ol;Levomenol
- CAS NO.:23089-26-1
- Empirical Formula: C15H26O
- Molecular Weight: 222.37
- MDL number: MFCD03412455
- EINECS: 245-423-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is (-)-alpha-bisabolol?
Absorption
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.
The Uses of (-)-alpha-bisabolol
(-)-α-Bisabolol was used to investigate the leishmanicidal and cytotoxic activity of essential oil of Vanillosmopsis arborea.
The Uses of (-)-alpha-bisabolol
Reference Standard in the analysis of herbal medicinal products
Background
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.
Indications
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
Definition
ChEBI: (-)-alpha-Bisabolol is a sesquiterpenoid.
General Description
(-)-α-Bisabolol is the major constituent of essential oil from leaves of Hymenocrater yazdianus.
Flammability and Explosibility
Not classified
Biochem/physiol Actions
α-Bisabolol is active against primary acute leukemia cells, including BCR-ABL(+) acute lymphoblastic leukemias. It is the inhibitor of voltage-dependent Ca(2+) channels in tracheal smooth muscle preparations of rat. It also inhibits human and rat glioma cell growth and survival. It is a potential new therapeutic agent against leishmaniasis.
Pharmacokinetics
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.
Metabolism
Not Available
Properties of (-)-alpha-bisabolol
Boiling point: | bp12 153° |
alpha | D -55.7°; D20 -51.02° (Günther) |
Density | d20 0.9211 |
vapor pressure | 0.015Pa at 20℃ |
FEMA | 4666 | ALPHA-BISABOLOL |
refractive index | n20/D 1.496 |
Flash point: | 135 °C |
storage temp. | -20°C |
solubility | DMSO:100.0(Max Conc. mg/mL);449.7(Max Conc. mM) |
pka | 15.04±0.29(Predicted) |
form | neat |
form | Liquid |
color | Colorless to light yellow |
Odor | at 100.00 %. fruity nutty coconut |
optical activity | [α]/D -60±2°, neat |
Water Solubility | 22mg/L at 20℃ |
JECFA Number | 2031 |
CAS DataBase Reference | 23089-26-1(CAS DataBase Reference) |
EPA Substance Registry System | Levomenol (23089-26-1) |
Safety information for (-)-alpha-bisabolol
Pictogram(s) |
Environment GHS09 |
GHS Hazard Statements |
H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. P501:Dispose of contents/container to..… |
Computed Descriptors for (-)-alpha-bisabolol
Abamectin manufacturer
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