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14462

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

functional group

hydroxyl

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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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
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
Takashi Seki et al.
Cancer science, 102(12), 2199-2205 (2011-09-03)
In the present study, we investigated whether α-bisabolol, a sesquiterpene alcohol present in essential oils derived from a variety of plants, has antitumor effects against pancreatic cancer. α-Bisabolol induced a decrease in cell proliferation and viability in pancreatic cancer cell
Christine Tschiggerl et al.
Plant foods for human nutrition (Dordrecht, Netherlands), 67(2), 129-135 (2012-03-14)
Chamomile (German Chamomile, Matricaria recutita L., Asteraceae) is one of the most popular medicinal plants in use as an herbal tea for food purposes and in folk medicine. Qualitative and semi-quantitative analyses of the volatile fraction of chamomile herbal tea
Seungbeom Kim et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(10), 2580-2585 (2011-07-21)
Although (-)-α-bisabolol, a natural monocyclic sesquiterpene alcohol, is often used as a cosmetic soothing supplement, little is known about its mechanisms of anti-inflammatory effects. Therefore, this study was designed to investigate anti-inflammatory effects of (-)-α-bisabolol and its mechanisms of action.
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