beta-bisabolol
(1S)-1-((1S)-1,5-dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol
Identification
| Name | beta-bisabolol |
| IUPAC | 4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol |
| CAS Number | 15352-77-9 |
| FDA UNII | LP618AV2EA |
| Molecular Formula | C15 H26 O |
| Molecular Weight | 222.37142000 |
| Nikkaji Number | J37.989A |
Regulatory
Physical Properties
| Appearance | colorless clear viscous liquid (est) |
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92110 @ 25.00 °C. |
| Refractive Index | 1.49630 @ 20.00 °C. |
| Boiling Point | 305.00 to 307.00 °C. @ 760.00 mm Hg |
| Flash Point | 267.00 °F. TCC ( 130.56 °C. ) |
| logP (o/w) | 4.639 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 100.00 %. |
| Taste Description | citrus lemon grapefruit |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| 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. |
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Potential Uses
Natural Occurrence
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
PubMed:
Essential oils composition of croton species from the Amazon.
PubMed:
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
PubMed:
Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla.
PubMed:
Antihyperalgesic and antiedematous activities of bisabolol-oxides-rich matricaria oil in a rat model of inflammation.
PubMed:
Chemotaxonomic importance of the essential-oil composition in two subspecies of Teucrium stocksianum Boiss. from Iran.
PubMed:
Essential oil of flowers of Anaphalis contorta, an aromatic and medicinal plant from India.
PubMed:
α-bisabolol is an effective proapoptotic agent against BCR-ABL(+) cells in synergism with Imatinib and Nilotinib.
PubMed:
Fast quality assessment of German chamomile (Matricaria chamomilla L.) by headspace solid-phase microextraction: influence of flower development stage.
PubMed:
STAT-3 inhibitory bisabolanes from Carthamus glaucus.
PubMed:
Psychopharmacological profile of Chamomile (Matricaria recutita L.) essential oil in mice.
PubMed:
Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas.
PubMed:
Inhibitory effects of (-)-α-bisabolol on LPS-induced inflammatory response in RAW264.7 macrophages.
PubMed:
Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.
PubMed:
Pro-apoptotic activity of α-bisabolol in preclinical models of primary human acute leukemia cells.
PubMed:
Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases.
PubMed:
Effect of topical heparin and levomenol on atopic dermatitis: a randomized four-arm, placebo-controlled, double-blind clinical study.
PubMed:
Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon.
PubMed:
In vivo effect of alpha-bisabolol, a nontoxic sesquiterpene alcohol, on the induction of spontaneous mammary tumors in HER-2/neu transgenic mice.
PubMed:
Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions.
PubMed:
alpha-Bisabolol induces dose- and time-dependent apoptosis in HepG2 cells via a Fas- and mitochondrial-related pathway, involves p53 and NFkappaB.
PubMed:
Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.
PubMed:
Validation of a high-performance liquid chromatography method for the determination of (-)-alpha-bisabolol from particulate systems.
PubMed:
Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.
PubMed:
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia.
PubMed:
Analysis of leaf volatiles of Zanthoxylum gillettii used in folk medicine of Cameroon.
PubMed:
Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.
PubMed:
Synthesis of beta-bisabolol by ring-closing olefin metathesis reaction.
PubMed:
Evaluation of mutagenic and antimutagenic activities of alpha-bisabolol in the Salmonella/microsome assay.
PubMed:
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
PubMed:
Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods.
PubMed:
New terpenoids in cultivated and wild chamomile (in vivo and in vitro).
PubMed:
Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone.
PubMed:
The ability of Bipolaris sorokiniana to modify geraniol and (-)-alpha-bisabolol as exogenous substrates.
PubMed:
Phase solubility studies of pure (-)-alpha-bisabolol and camomile essential oil with beta-cyclodextrin.
PubMed:
Anthocyanin, bisabolol and phenylammonialyase activity in cell cultures of Populus deltoides.
PubMed:
[Study of tolerance and efficacy of cosmetic preparations with lenitive action in atopic dermatitis in children].
PubMed:
Antennal olfactory responsiveness ofMicroplitis croceipes (Hymenoptera: Braconidae) to cotton plant volatiles.
PubMed:
Determination of alpha-bisabolol and d-panthenol in cosmetic products by gas chromatography.
PubMed:
Orientation of boll weevil,Anthonomus grandis boh. (Coleoptera: Curculionidae), to pheromone and volatile host compound in the laboratory.
PubMed:
Electroantennogram responses ofTrirhabda bacharides (weber) (Coleoptera: Chrysomelidae) to plant volatiles.
PubMed:
Olfaction in the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae): Electroantennogram studies.
PubMed:
Isolation and identification of cotton synomones mediating searching behavior by parasitoidCampoletis sonorensis.
PubMed:
Identification and quantitative analysis of the volatile substances emitted by maturing cotton in the field.