cubebol
(3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
 
Notes:
None found
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(3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol (Click)
CAS Number: 23445-02-5Picture of molecule
FDA UNII: 9C9ZTS2B3U
Nikkaji Web: J16.596D
XlogP3-AA: 3.90 (est)
Molecular Weight: 222.37142000
Formula: C15 H26 O
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 2028  cubebol
FEMA Number: 4497  cubebol
FDA Mainterm: CUBEBOL
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Physical Properties:
Appearance: white crystalline solid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 64.00 to  65.00 °C. @ 760.00 mm Hg
Boiling Point: 279.00 to  280.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.000480 mm/Hg @ 25.00 °C. (est)
Flash Point: 242.00 °F. TCC ( 116.67 °C. )
logP (o/w): 4.592 (est)
Soluble in:
 alcohol
 water, slightly
 water, 3.12 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Description:
spicy minty
  
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Cosmetic Information:
None found
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Suppliers:
Axsyn
For experimental / research use only.
1H-Cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol,octahydro-3,7-dimethyl-4-(1-methylethyl)-, (3S,3aR,3bR,4S,7R,7aR)-
Parchem
cubebol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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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: flavoring agents
Recommendation for cubebol usage levels up to:
 not for fragrance use.
 
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 24
Click here to view publication 24
 average usual ppmaverage maximum ppm
baked goods: 1.0000030.00000
beverages(nonalcoholic): 1.0000030.00000
beverages(alcoholic): 1.0000030.00000
breakfast cereal: 1.0000030.00000
cheese: --
chewing gum: 1.0000030.00000
condiments / relishes: --
confectionery froastings: 1.0000030.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 1.0000020.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: 1.0000020.00000
gravies: --
hard candy: 1.0000020.00000
imitation dairy: --
instant coffee / tea: 1.0000020.00000
jams / jellies: 1.0000010.00000
meat products: --
milk products: 1.0000010.00000
nut products: 1.0000010.00000
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 1.0000030.00000
soups: --
sugar substitutes: 1.0000030.00000
sweet sauces: 1.0000030.00000
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Safety References:
EPI System: View
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11276107
National Institute of Allergy and Infectious Diseases: Data
 (3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
Chemidplus: 0023445025
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References:
 (3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11276107
Pubchem (sid): 42355570
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
FDA Everything Added to Food in the United States (EAFUS): View
CHEBI: View
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
FAO: Cubebol
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cedarwood oil virginia @ 0.10%
Data  GC  Search Trop  Picture
 cubeb oil @ 15.18%
Data  GC  Search Trop  Picture
 false cubebs oil
Search Trop  Picture
 geranium rose-scented oil (pelargonium spp.) cuba @ 0.60%
Data  GC  Search Trop  Picture
 lavandin oil abrialis @ trace%
Data  GC  Search Trop  Picture
 mandarin oil uruguay @ trace%
Data  GC  Search Trop  Picture
 mikania cordata (burm. f.) b.l. robinson var. cordata leaf oil france @ 0.20%
Data  GC  Search Trop  Picture
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Synonyms:
 cubeb camphor
1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol,octahydro-3,7-dimethyl-4-(1-methylethyl)-, (3S,3aR,3bR,4S,7R,7aR)-
(3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
(3S,3aR,3bR, 4S,7R,7aR)-octahydro-3,7-dimethyl-4-(1-methyl ethyl)-1H-cyclopenta(1,3)cyclopropa(1,2)benzen-3-ol
(-)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol
(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol
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Articles:
Google Patents: Use of cubebol as a flavoring ingredient
PubMed: Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations.
PubMed: Identification of cryptic species within liverwort Conocephalum conicum based on the volatile components.
PubMed: [Sesquiterpenes from stem of Schisandra glaucescens].
PubMed: Inter-population variability of terpenoid composition in leaves of Pistacia lentiscus L. from Algeria: a chemoecological approach.
PubMed: Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers.
PubMed: Enhancement of farnesyl diphosphate pool as direct precursor of sesquiterpenes through metabolic engineering of the mevalonate pathway in Saccharomyces cerevisiae.
PubMed: Stereocontrolled syntheses of (-)-cubebol and (-)-10-epicubebol involving intramolecular cyclopropanation of alpha-lithiated epoxides.
PubMed: Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: evidence of chirality transfer and mechanistic insights.
PubMed: Enhancing sesquiterpene production in Saccharomyces cerevisiae through in silico driven metabolic engineering.
PubMed: Mosquito larvicidal activities of extractives from black heartwood-type Cryptomeria japonica.
PubMed: Antifeedants against Locusta migratoria from the Japanese Cedar, Cryptomeria japonica II.
PubMed: Production of plant sesquiterpenes in Saccharomyces cerevisiae: effect of ERG9 repression on sesquiterpene biosynthesis.
PubMed: Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: evidence for chirality transfer.
PubMed: Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates: total syntheses of (-)-alpha-cubebene, (-)-cubebol, sesquicarene and related terpenes.
PubMed: [Isolation and preparation of sesquiterpenols from the Japanese cedar, Cryptomeria japonica D. Don, by preparative reversed-phase high performance liquid chromatography and its characterization].
PubMed: Antifeedants against Acusta despesta from the Japanese cedar, Cryptomeria japonica II.
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