Structure Database (LMSD)
Common Name
(-)-alpha-Bisabolol
Systematic Name
Synonyms
3D model of (-)-alpha-Bisabolol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
(–)-α-Bisabolol is a sesquiterpene alcohol that has been found in the essential oils of several aromatic plants, including C. sativa, C. indica, and C. sativa/C. indica hybrid strains, with diverse biological activities.1,2,3,4,5 It inhibits the growth of L. amazonensis promastigotes and amastigotes (IC50s = 8.07 and 4.29 μg/ml, respectively).2 It also reduces the growth of L. infantum and L. donovani amastigotes (IC50s = 56.9 and 39.4 μM, respectively) with a cytotoxic concentration (CC50) value of greater than 1,000 μM in L929 cells.3 In vivo, (–)-α-bisabolol (200 mg/kg) reduces parasite load in the liver and spleen in a mouse model of visceral leishmaniasis. (–)-α-Bisabolol (200 mg/kg) reduces the size of ethanol-induced lesions, decreases malondialdehyde (MDA) production, and increases superoxide dismutase (SOD) activity in gastric mucosa in mice.4 It also decreases serotonin-, carrageenan-, and dextran-, but not histamine-, induced paw edema as well as acetic-acid induced writhing and paw-licking time in the formalin test in mice, indicating anti-inflammatory and antinociceptive activity.5
This information has been provided by Cayman Chemical
References
1. Rocha, N.F., Rios, E.R., Carvalho, A.M., et al. Anti-nociceptive and anti-inflammatory activities of (−)-α-bisabolol in rodents. Naunyn Schmiedebergs Arch. Pharmacol. 384(6), 525-533 (2011).
5. Elzinga, S., Fischedick, J., Podkolinski, R., et al. Cannabinoids and terpenes as chemotaxonomic markers in Cannabis. Nat. Prod. Chem. Res. 3(4), 181 (2015).
String Representations
InChiKey (Click to copy)
RGZSQWQPBWRIAQ-CABCVRRESA-N
InChi (Click to copy)
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/t14-,15+/m1/s1
SMILES (Click to copy)
[C@@]1([H])(CC=C(C)CC1)[C@](O)(C)CC/C=C(\C)/C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
16
Rings
1
Aromatic Rings
0
Rotatable Bonds
4
Van der Waals Molecular Volume
259.21
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
4.52
Molar Refractivity
70.90
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Updated at
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