(3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol

CAS: 23445-02-5 C15 H26 O MW: 222.37142000

Identification

Namecubebol
IUPAC(3S,3aR,3bR,4S,7R,7aR)-3,7-dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
CAS Number23445-02-5
FDA UNII9C9ZTS2B3U
Molecular FormulaC15 H26 O
Molecular Weight222.37142000
Nikkaji NumberJ16.596D

Regulatory

JECFA Food Flavoring2028 cubebol
FEMA Number4497
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)23445-02-5 ; CUBEBOL

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 mmHg @ 25.00 °C. (est)
Flash Point 242.00 °F. TCC ( 116.67 °C. )
logP (o/w) 4.592 (est)
Soluble in alcohol
Insoluble in water

Organoleptic Properties

Odor Description spicy minty

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for cubebol usage levels up tonot for fragrance use.
Structure ClassI
baked goods1.00000
beverages(nonalcoholic)1.00000
beverages(alcoholic)1.00000
breakfast cereal1.00000
cheese-
chewing gum1.00000
condiments / relishes-
confectionery froastings1.00000
egg products-
fats / oils-
fish products-
frozen dairy1.00000
fruit ices-
gelatins / puddings-
granulated sugar1.00000
gravies-
hard candy1.00000
imitation dairy-
instant coffee / tea1.00000
jams / jellies1.00000
meat products-
milk products1.00000
nut products1.00000
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy1.00000
soups-
sugar substitutes1.00000
sweet sauces1.00000

Chemical sources Association Inc

Exchange of knowledge

Need This Item for Flavor? You can contact the Chemical Sources Association.

Potential Uses

None Found

Natural Occurrence

cedarwood oil virginia @ 0.10% Data cubeb oil @ 15.18% Data false cubebs oil geranium rose-scented oil (pelargonium spp.) cuba @ 0.60% Data lavandin oil abrialis @ trace% Data mandarin oil uruguay @ trace% Data mikania cordata (burm. f.) b.l. robinson var. cordata leaf oil france @ 0.20% Data

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-iso propyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol (1R,4S,5R,6R,7S,10R)-7-iso propyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol 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.