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beta-bisabolol

Chemical Structure

General Material Information

Preferred name beta-bisabolol
Trivial Name β-Bisabolol
Short Description (1S)-1-((1S)-1,5-dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol
Formula C15 H26 O
CAS Number 15352-77-9
FDA UNII LP618AV2EA
Nikkaji Number J37.989A
xLogP3-AA 4.00 (est)
NMR Predictor External link
Synonyms
  • .beta.- bisabolol
  • 3-cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-
  • (1S)-1-((1S)-1,5-dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol
  • (S-(R*,R*))-1-(1,5-dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol
  • 4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol
  • 4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol
  • 3-Cyclohexen-1-ol, 1-[(1S)-1,5-dimethyl-4-hexen-1-yl]-4-methyl-, (1S)-
  • 3-Cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-
  • 3-Cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-, [S-(R*,R*)]-
  • 3-Cyclohexen-1-ol, 1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-, (1S)-
  • (1S)-1-[(1S)-1,5-Dimethyl-4-hexen-1-yl]-4-methyl-3-cyclohexen-1-ol
  • β-Bisabolol

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Literature & References

4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):27208
Pubchem (sid):134993116
Flavornet:15352-77-9
Pherobase:View
Publications by PubMed
Essential oils composition of croton species from the Amazon.
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla.
Antihyperalgesic and antiedematous activities of bisabolol-oxides-rich matricaria oil in a rat model of inflammation.
Chemotaxonomic importance of the essential-oil composition in two subspecies of Teucrium stocksianum Boiss. from Iran.
Essential oil of flowers of Anaphalis contorta, an aromatic and medicinal plant from India.
α-bisabolol is an effective proapoptotic agent against BCR-ABL(+) cells in synergism with Imatinib and Nilotinib.
Fast quality assessment of German chamomile (Matricaria chamomilla L.) by headspace solid-phase microextraction: influence of flower development stage.
STAT-3 inhibitory bisabolanes from Carthamus glaucus.
Psychopharmacological profile of Chamomile (Matricaria recutita L.) essential oil in mice.
Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas.
Inhibitory effects of (-)-α-bisabolol on LPS-induced inflammatory response in RAW264.7 macrophages.
Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.
Pro-apoptotic activity of α-bisabolol in preclinical models of primary human acute leukemia cells.
Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases.
Effect of topical heparin and levomenol on atopic dermatitis: a randomized four-arm, placebo-controlled, double-blind clinical study.
Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon.
In vivo effect of alpha-bisabolol, a nontoxic sesquiterpene alcohol, on the induction of spontaneous mammary tumors in HER-2/neu transgenic mice.
Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions.
alpha-Bisabolol induces dose- and time-dependent apoptosis in HepG2 cells via a Fas- and mitochondrial-related pathway, involves p53 and NFkappaB.
Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.
Validation of a high-performance liquid chromatography method for the determination of (-)-alpha-bisabolol from particulate systems.
Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia.
Analysis of leaf volatiles of Zanthoxylum gillettii used in folk medicine of Cameroon.
Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.
Synthesis of beta-bisabolol by ring-closing olefin metathesis reaction.
Evaluation of mutagenic and antimutagenic activities of alpha-bisabolol in the Salmonella/microsome assay.
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods.
New terpenoids in cultivated and wild chamomile (in vivo and in vitro).
Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone.
The ability of Bipolaris sorokiniana to modify geraniol and (-)-alpha-bisabolol as exogenous substrates.
Phase solubility studies of pure (-)-alpha-bisabolol and camomile essential oil with beta-cyclodextrin.
Anthocyanin, bisabolol and phenylammonialyase activity in cell cultures of Populus deltoides.
[Study of tolerance and efficacy of cosmetic preparations with lenitive action in atopic dermatitis in children].
Antennal olfactory responsiveness ofMicroplitis croceipes (Hymenoptera: Braconidae) to cotton plant volatiles.
Determination of alpha-bisabolol and d-panthenol in cosmetic products by gas chromatography.
Orientation of boll weevil,Anthonomus grandis boh. (Coleoptera: Curculionidae), to pheromone and volatile host compound in the laboratory.
Electroantennogram responses ofTrirhabda bacharides (weber) (Coleoptera: Chrysomelidae) to plant volatiles.
Olfaction in the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae): Electroantennogram studies.
Isolation and identification of cotton synomones mediating searching behavior by parasitoidCampoletis sonorensis.
Identification and quantitative analysis of the volatile substances emitted by maturing cotton in the field.

Suppliers

BOC Sciences

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Specific gravity @ 25 °C
Pounds per Gallon
Boiling Point 305 to 307°C @ 760 mm Hg
Flash Point TCC Value 130.56 °C TCC
logP (o/w) 4.639 est
Solubility
alcohol Yes
water, 1.688 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Citrus
citrus, floral, tart, lemon, fresh, sweet, herbal
General comment At 100.00 %. citrus floral tangy lemon fresh sweet herbal
Flavor Type: Citrus
citrus, lemon, grapefruit
General comment Citrus lemon grapefruit

Occurrences

Potential Uses

Applications
Odor purposes Ginger, Grapefruit, Lemon, Lime, Orange
Other purposes Fixer

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for beta-bisabolol usage levels up to:
4.0000 % in the fragrance concentrate.
Recommendation for beta-bisabolol flavor usage levels up to:
30.0000 ppm in the finished product.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :27208
National Institute of Allergy and Infectious Diseases:Data
4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol
Chemidplus:0015352779