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Sigma-Aldrich

(−)-α-Bisabolol

≥93% (GC)

Synonym(s):

(-)-alpha-Bisabolol, (−)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol, Levomenol

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About This Item

Empirical Formula (Hill Notation):
C15H26O
CAS Number:
23089-26-1
Molecular Weight:
222.37
EC Number:
208-205-9
MDL number:
MFCD03412455
UNSPSC Code:
12352100
PubChem Substance ID:
57647161
NACRES:
NA.22

Assay

≥93% (GC)

optical activity

[α]/D -58±5°, neat

refractive index

n20/D 1.496

SMILES string

C\C(C)=C\CC[C@](C)(O)[C@H]1CCC(C)=CC1

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

InChI key

RGZSQWQPBWRIAQ-CABCVRRESA-N

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General description

(-)-α-Bisabolol is the major constituent of essential oil from leaves of Hymenocrater yazdianus.

Application

(-)-α-Bisabolol was used to investigate the leishmanicidal and cytotoxic activity of essential oil of Vanillosmopsis arborea.

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.

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

289.4 °F - closed cup

Flash Point(C)

143 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Aracélio Viana Colares et al.
Evidence-based complementary and alternative medicine : eCAM, 2013, 727042-727042 (2013-08-13)
The search for new immunopharmacological chemical agents to treat various diseases caused by bacteria, fungi, and protozoa, such as leishmaniasis, for example, has led to the exploration of potential products from plant species and their main active ingredients. Antimonial drugs
Shiva Masoudi et al.
Natural product communications, 7(1), 117-120 (2012-03-21)
Water-distilled essential oils from leaves of Hymenocrater yazdianus Rech.f., flowers of Stachys obtusicrena Boiss., and stems and flowers of Nepeta asterotricha Rech.f., which are endemic to Iran, were analyzed by GC and GC/MS. Fifty-five components of the leaf oil of
Rodrigo J B de Siqueira et al.
Canadian journal of physiology and pharmacology, 90(1), 23-35 (2011-12-17)
The present study deals with the pharmacological effects of the sesquiterpene alcohol (-)-α-bisabolol on various smooth-muscle preparations from rats. Under resting tonus, (-)-α-bisabolol (30-300 µmol/L) relaxed duodenal strips, whereas it showed biphasic effects in other preparations, contracting endothelium-intact aortic rings and
Maryam Yousefi et al.
Natural product research, 25(17), 1629-1634 (2011-10-21)
A study on the volatile oil of Ferula behboudiana by gas chromatography and gas chromatography-mass spectrometry showed the presence of 27 compounds. Two disulphide derivatives, 1-sec-butyl-2-[(E)-3-(methylthio) prop-1-enyl] disulphane (1) and 1-sec-butyl-2-[(Z)-3-(methylthio)prop-1-enyl] disulphane (2) (59.4%), were isolated from the oil by
Orazio Taglialatela-Scafati et al.
Journal of natural products, 75(3), 453-458 (2012-02-09)
Apart from a large amount (ca. 2.0%) of α-bisabolol β-D-fucopyranoside (2a), the aerial parts of the Mediterranean weed Carthamus glaucus afforded an unusual triglyceride (E-2-crotonyl-1,3-distearolylglycerol, 7), two lipophilic flavonoids (6a,b), and a series of bisabolane fucopyranosides variously acylated on the
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