beta-bisabolol
(1S)-1-((1S)-1,5-dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol
 
Notes:
Constit. of Gossypium hirsutum (cotton) oil and other essential oils
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4-methyl-1-(6-methylhept-5-en-2-yl)cyclohex-3-en-1-ol (Click)
CAS Number: 15352-77-9Picture of molecule
FDA UNII: LP618AV2EA
Nikkaji Web: J37.989A
XlogP3-AA: 4.00 (est)
Molecular Weight: 222.37142000
Formula: C15 H26 O
NMR Predictor: Predict (works with chrome or firefox)
Category: flavor and fragrance agents
 
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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
 water, 1.688 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Type: citrus
Odor Strength: medium
 citrus  floral  tart  lemon  fresh  sweet  herbal  
Odor Description:
at 100.00 %. 
citrus floral tangy lemon fresh sweet herbal
 citrus  lemon  grapefruit  
Taste Description:
citrus lemon grapefruit
  
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Cosmetic Information:
None found
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Suppliers:
 None found
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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
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Safety in Use Information:
Category: flavor and fragrance agents
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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Safety References:
EPI System: View
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
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): HMDB36111
FooDB: FDB014957
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
For Odor
aldehydic
aldehydic
 decanal (aldehyde C-10)FL/FR
 mandarine undecenalFL/FR
 TMH aldehydeFR
balsamic
isobornyl acetateFL/FR
isobornyl phenyl acetateFL/FR
 fenchyl acetateFL/FR
citronella
4,8-dimethyl-7-nonen-2-olFR
citrus
 acetaldehyde citronellyl methyl acetalFR
 bergamot oilFL/FR
 bergamot oil bergaptene reduced italyFL/FR
 bergamot oil turkeyFL/FR
 citral diethyl acetalFL/FR
 citral dimethyl acetalFL/FR
 citrus floral green fragranceFR
 citrus ocimenolFR
 citrus specialtyFR
 dihydromyrcenolFL/FR
2,4-dimethyl-3-cyclohexene-1-methanyl acetateFR
2-dodecanoneFL/FR
2-ethyl-1-hexanolFL/FR
citrus floral fragranceFR
 grapefruit oil terpenesFL/FR
2-heptanolFL/FR
 lemon oil terpenesFL/FR
 lemongrass oilFL/FR
 lemongrass oil terpenesFL/FR
 lime octadienalFR
 lime oil distilled mexicoFL/FR
 lime oil terpenesFL/FR
 mandarin oilFL/FR
 mandarin oil (citrus reticulata nova var. mandarin) uruguayFL/FR
 mandarin oil italyFL/FR
 melissa oil slovak republic 
3-methyl-4-(2-methyl butyl oxy) butyraldehydeFR
 nonanal dimethyl acetalFL/FR
(+)-nootkatoneFL/FR
 petitgrain combava oilFR
(±)-2,4,8-trimethyl-7-nonen-2-olFL/FR
10-undecen-1-olFL/FR
 verbena absolute franceFL/FR
 verbena fragranceFR
 verbena oil terpenelessFL/FR
earthy
(Z)-4-octen-1-olFL/FR
floral
isoamyl salicylateFL/FR
 bois de rose oil brazilFL/FR
 butyl tiglateFR
 citronellalFL/FR
2,4-dimethyl-3-cyclohexene-1-methanolFR
 ethyl linaloolFR
 ethyl linalyl acetalFR
 gardenia acetalFR
 herbal pyranFR
 karo karounde absoluteFR
abrialis lavandin oilFL/FR
 lavandula angustifolia flower oilFL/FR
 lavender oilFL/FR
 lavender oil franceFL/FR
 lavender oil greeceFL/FR
 linaloolFL/FR
para-methyl benzyl acetateFL/FR
 methyl benzyl acetate (mixed ortho-,meta-,para-)FL/FR
(Z)-methyl epi-jasmonateFL/FR
 muguet nitrileFR
 muguet octadienolFR
 nerolFL/FR
 neroli oil tunisiaFL/FR
 nerolidyl acetateFL/FR
(R)-ocean propanal 
(Z)-beta-ocimeneFL/FR
 palmarosa oilFL/FR
 peony acetonitrileFR
 petitgrain concreteFR
 petitgrain grapefruit oilFL/FR
 petitgrain lemon oilFL/FR
 petitgrain oil moroccoFL/FR
 petitgrain oil terpenelessFL/FR
isophytolFL/FR
 prenyl salicylateFL/FR
 rose undeceneFR
 terpinyl isobutyrateFL/FR
 tetrahydrolinalyl acetateFR
(S)-2,5,6-trimethyl-2-heptanol 
 undecanal dimethyl acetalFR
fresh
 fresh & clean fragranceFR
fruity
 ethyl 3-hydroxyhexanoateFL/FR
 eucalyptus staigeriana oilFR
sesquiphellandrene 
fungal
 hydroxymethyl hexyl ethyl ketoneFL/FR
green
isobutyl benzyl carbinolFL/FR
 heptyl formateFL/FR
herbal
 arnica flower oilFR
 carrot seed oil (daucus carota ssp. gummifer hook. fil.) spainFR
 chamomile isobutyrateFR
 chrysanthemum ketoneFR
 freesia heptanolFL/FR
 lavender absolute bulgariaFL/FR
 lavender absolute franceFL/FR
 lavender concreteFL/FR
 lavender oil terpenelessFL/FR
 lavender oil terpenesFL/FR
 lavender stem oil lithuaniaFR
 matricaria chamomilla flower oilFL/FR
 myrtle oilFL/FR
 tea leaf absoluteFL/FR
alpha-terpinyl acetateFL/FR
 caraway seed oleoresinFL/FR
 gingergrass oilFR
sulfurous
4-tropical oxathianeFL/FR
terpenic
(E,E)-2,6-alloocimeneFL/FR
alpha-terpineolFL/FR
tobacco
2,6,6-trimethyl-2-hydroxycyclohexanoneFL/FR
waxy
 decanal dimethyl acetalFL/FR
1,8-octane dinitrile 
1-undecanolFL/FR
woody
cis-3-tert-butyl cyclohexyl acetate 
2-decalinyl acetateFR
alpha-terpineneFL/FR
 zdravetz oilFL/FR
 
For Flavor
 
No flavor group found for these
isobornyl phenyl acetateFL/FR
cis-3-tert-butyl cyclohexyl acetate 
 capsicum oleoresin CO2 extractFL
 decanal dimethyl acetalFL/FR
8,9-dehydrotheaspironeFL
 fenchyl acetateFL/FR
 hydroxymethyl hexyl ethyl ketoneFL/FR
pseudoiononeFL
 lavender oil terpenesFL/FR
 mandarine undecenalFL/FR
 melissa oil slovak republic 
para-methyl benzyl acetateFL/FR
 methyl benzyl acetate (mixed ortho-,meta-,para-)FL/FR
 nerolidyl acetateFL/FR
 nonanal dimethyl acetalFL/FR
(R)-ocean propanal 
(E,E)-2,6-alloocimeneFL/FR
1,8-octane dinitrile 
(Z)-4-octen-1-olFL/FR
sesquiphellandrene 
 tea leaf absoluteFL/FR
 terpinyl isobutyrateFL/FR
(S)-2,5,6-trimethyl-2-heptanol 
2,6,6-trimethyl-2-hydroxycyclohexanoneFL/FR
10-undecen-1-olFL/FR
 zdravetz oilFL/FR
acidic
(E)-2-hexenoic acidFL
aldehydic
1-undecanolFL/FR
amber
isobutyl benzyl carbinolFL/FR
citrus
 bergamot oilFL/FR
 bergamot oil bergaptene reduced italyFL/FR
 bergamot oil turkeyFL/FR
 citral diethyl acetalFL/FR
 citral dimethyl acetalFL/FR
 freesia heptanolFL/FR
 grapefruit oil terpenesFL/FR
 lemon oil terpenesFL/FR
 lemongrass oilFL/FR
 lemongrass oil terpenesFL/FR
 lime oil distilled mexicoFL/FR
 lime oil terpenesFL/FR
 linaloolFL/FR
 mandarin oilFL/FR
 mandarin oil (citrus reticulata nova var. mandarin) uruguayFL/FR
 mandarin oil italyFL/FR
 nerolFL/FR
 neroli oil tunisiaFL/FR
(+)-nootkatoneFL/FR
 petitgrain grapefruit oilFL/FR
 petitgrain lemon oilFL/FR
 petitgrain oil moroccoFL/FR
 petitgrain oil terpenelessFL/FR
alpha-terpineolFL/FR
(±)-2,4,8-trimethyl-7-nonen-2-olFL/FR
 verbena absolute franceFL/FR
 verbena oil terpenelessFL/FR
fatty
2-dodecanoneFL/FR
2-ethyl-1-hexanolFL/FR
 heptyl formateFL/FR
floral
 bois de rose oil brazilFL/FR
 citronellalFL/FR
(Z)-methyl epi-jasmonateFL/FR
 palmarosa oilFL/FR
fruity
 ethyl 3-hydroxyhexanoateFL/FR
2-heptanolFL/FR
4-tropical oxathianeFL/FR
green
isoamyl salicylateFL/FR
 dihydromyrcenolFL/FR
(E,E)-2,4-hexadienalFL
(Z)-beta-ocimeneFL/FR
herbal
abrialis lavandin oilFL/FR
 lavandula angustifolia flower oilFL/FR
 lavender absolute bulgariaFL/FR
 lavender absolute franceFL/FR
 lavender concreteFL/FR
 lavender oilFL/FR
 lavender oil franceFL/FR
 lavender oil greeceFL/FR
 lavender oil terpenelessFL/FR
 matricaria chamomilla flower oilFL/FR
 prenyl salicylateFL/FR
oily
isophytolFL/FR
spicy
 caraway seed oleoresinFL/FR
 myrtle oilFL/FR
terpenic
alpha-terpineneFL/FR
waxy
 decanal (aldehyde C-10)FL/FR
woody
isobornyl acetateFL/FR
alpha-terpinyl acetateFL/FR
 
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Potential Uses:
 fixer 
 gingerFR
 grapefruitFR
 lemonFR
 limeFR
 orangeFR
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Occurrence (nature, food, other): note
 ayou wood oil @ 8.30%
Data  GC  Search Trop  Picture
 bergamot oil @ trace%
Data  GC  Search  Picture
 bombycilaena erecta oil greece @ 0.30%
Data  GC  Search Trop  Picture
 cascarilla bark oil @ trace%
Data  GC  Search Trop  Picture
 cedrela wood oil @ 0.53%
Data  GC  Search Trop  Picture
 cotton levant cotton buds
Search Trop  Picture
 curcuma amada roxb. rhizome oil india @ 0.50%
Data  GC  Search Trop  Picture
 ginger rhizome
Search Trop  Picture
 ginger rhizome oil
Search Trop  Picture
 guava leaf oil cuba @ 3.20%
Data  GC  Search Trop  Picture
 lavandin oil abrialis @ 0.24%
Data  GC  Search Trop  Picture
 lavandin oil grosso @ 0.40%
Data  GC  Search Trop  Picture
 lavender oil spike france @ 0.02%
Data  GC  Search Trop  Picture
 lemon
Search Trop  Picture
 lemongrass oil @ 0.37%
Data  GC  Search Trop  Picture
 pepper black pepper fruit oil
Search Trop  Picture
 pepper oil black india @ 0.20%
Data  GC  Search Trop  Picture
 phlomis fruticosa l. flower oil greece @ 3.50%
Data  GC  Search Trop  Picture
 phoebe oil brazil @ 2.50%
Data  GC  Search Trop  Picture
 sandalwood oil east indian @ 0.64%
Data  GC  Search Trop  Picture
Synonyms   Articles   Notes   Search   Top
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
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Articles:
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.
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