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
Identification
| Name | cubebol |
| 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 Number | 23445-02-5 |
| FDA UNII | 9C9ZTS2B3U |
| Molecular Formula | C15 H26 O |
| Molecular Weight | 222.37142000 |
| Nikkaji Number | J16.596D |
Regulatory
| JECFA Food Flavoring | 2028 cubebol |
| FEMA Number | 4497 |
| FDA | No 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 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 | flavoring agents |
| Recommendation for cubebol usage levels up to | not for fragrance use. |
| Structure Class | I |
| baked goods | 1.00000 |
| beverages(nonalcoholic) | 1.00000 |
| beverages(alcoholic) | 1.00000 |
| breakfast cereal | 1.00000 |
| cheese | - |
| chewing gum | 1.00000 |
| condiments / relishes | - |
| confectionery froastings | 1.00000 |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 1.00000 |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | 1.00000 |
| gravies | - |
| hard candy | 1.00000 |
| imitation dairy | - |
| instant coffee / tea | 1.00000 |
| jams / jellies | 1.00000 |
| meat products | - |
| milk products | 1.00000 |
| nut products | 1.00000 |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | 1.00000 |
| soups | - |
| sugar substitutes | 1.00000 |
| sweet sauces | 1.00000 |
Chemical sources Association Inc
Exchange of knowledge
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Potential Uses
Natural Occurrence
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.