beta-cedrene
(1S,2R,5S)-8-methylene-2,6,6-trimethyl tricyclo(5.3.1.01.5)undecane
Identification
| Name | beta-cedrene |
| IUPAC | (3R-(3alpha, 3abeta,7beta,8aalpha))-octahydro-3,8,8-trimethyl-6-methylene-1H-3a,7-methanoazulene |
| CAS Number | 546-28-1 |
| EINECS | 208-898-8 |
| FDA UNII | 6QL7ERD5Q1 |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| MDL Number | MFCD00270433 |
| Beilstein | 2244722 |
Regulatory
Physical Properties
| Appearance | colorless to yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.93000 to 0.93600 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.739 to 7.788 |
| Refractive Index | 1.49800 to 1.50400 @ 20.00 °C. |
| Boiling Point | 263.00 to 264.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.017000 mmHg @ 25.00 °C. (est) |
| Flash Point | 230.00 °F. TCC ( 110.00 °C. ) |
| logP (o/w) | 6.226 (est) |
| Shelf Life | 6.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| 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 |
| IFRA Critical Effect | Dermal sensitization |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.012 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 7.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 5.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 10.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 20.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
cedr-8(15)-ene
(+)-beta-
cedrene
1H-3a,7-
methanoazulene, octahydro-3,8,8-trimethyl-6-methylene-, (3R-(3a,3ab,7b,8aa))-
1H-3a,7-
methanoazulene, octahydro-3,8,8-trimethyl-6-methylene-, (3R,3aS,7S,8aS)-
1H-3a,7-
methanoazulene, octahydro-3,8,8-trimethyl-6-methylene-, [3R-(3a,3ab,7b,8aa)]-
(1S,2R,5S)-8-
methylene-2,6,6-trimethyl tricyclo(5.3.1.01.5)undecane
(3R-(3a,3Ab,7b,8aa))-
octahydro-3,8,8-trimethyl-6-methylene-1H-3a,7-methanoazulene
(3R-(3alpha, 3abeta,7beta, 8aalpha))-
octahydro-3,8,8-trimethyl-6-methylene-1H-3a,7-methanoazulene
PubMed:
Chemical Constituents from Sinningia canescens and S. warmingii.
PubMed:
Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh, India.
PubMed:
Inhibitory effects of cedrol, β-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes.
PubMed:
Effect of gibberellic acid (GA), indole acetic acid (IAA) and benzylaminopurine (BAP) on the synthesis of essential oils and the isomerization of methyl chavicol and trans-anethole in Ocimum gratissimum L.
PubMed:
Reprogramming the chemodiversity of terpenoid cyclization by remolding the active site contour of epi-isozizaene synthase.
PubMed:
Identification of volatile compounds emitted by Artemisia ordosica (Artemisia, Asteraceae) and changes due to mechanical damage and weevil infestation.
PubMed:
Comparative study of the volatiles' composition of healthy and larvae-infested Artemisia ordosica.
PubMed:
Composition, anticancer, and antimicrobial activities in vitro of the heartwood essential oil of Cunninghamia lanceolata var. konishii from Taiwan.
PubMed:
Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza.
PubMed:
Essential oil composition and antibacterial activity of Monticalia greenmaniana (Asteraceae).
PubMed:
Degradation of terpenes and terpenoids from Mediterranean rangelands by mixed rumen bacteria in vitro.
PubMed:
Essential oils of Cupressus funebris, Juniperus communis, and J. chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes.
PubMed:
Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides.
PubMed:
Comparative analysis of essential oils of six Anthemis taxa from Serbia and Montenegro.
PubMed:
Chemical compositions and antioxidant/antimicrobial activities of various samples prepared from Schinus terebinthifolius leaves cultivated in Egypt.
PubMed:
[Analysis of essential oil from different organs of Caryopteris tangutica].
PubMed:
Antimicrobial activity of extractable conifer heartwood compounds toward Phytophthora ramorum.
PubMed:
Changes in terpene content in milk from pasture-fed cows.
PubMed:
Antimicrobial activity of some Pacific Northwest woods against anaerobic bacteria and yeast.
PubMed:
Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes alpha- and beta-cedrene.
PubMed:
Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.
PubMed:
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.