alpha-cedrene
(1S,2R,5S)-2,6,6,8-tetramethyl tricyclo(5.3.1.01.5)undec-8-ene
Identification
| Name | alpha-cedrene |
| IUPAC | (3R-(3a,3ab,7b,8aa))-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene |
| CAS Number | 469-61-4 |
| EINECS | 207-418-4 |
| FDA UNII | 50D4A81G8T |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| MDL Number | MFCD00063003 |
| Beilstein | 3196861 |
| CoE Number | 10985 |
Regulatory
Physical Properties
| Appearance | colorless clear oily liquid (est) |
| Assay | 95.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92600 to 0.93700 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.705 to 7.797 |
| Refractive Index | 1.50000 to 1.50300 @ 20.00 °C. |
| Boiling Point | 261.00 to 262.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.018000 mmHg @ 25.00 °C. (est) |
| Flash Point | 219.00 °F. TCC ( 103.89 °C. ) |
| logP (o/w) | 6.308 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | 112 hour(s) at 100.00 % |
| Odor Description | at 100.00 %. |
| Odor sample from | Elan Inc. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Human Experience | 5 % solution: no irritation or sensitization. |
| 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
(-)-a-
cedrene
(-)-alpha-
cedrene
L-alpha-
cedrene
laevo-alpha-
cedrene
levo-a-
cedrene
alpha-
cedrene 60% natural
(3R- (3alpha,3abeta, 7beta,8aalpha))- 2,3,4,7,8,8a-
hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene
1H-3a,7-
methanoazulene, 2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-, (3R,3aS,7S,8aS)-
(1S,2R,5S)-2,6,6,8-
tetramethyl tricyclo(5.3.1.01.5)undec-8-ene
PubMed:
[Analysis of Volatile Oils from Different Processed Products of Zingiber officinale Rhizome by GC-MS].
PubMed:
Metabolite Profiling and Comparison of Bioactivity in Antrodia cinnamomea and Antrodia salmonea Fruiting Bodies.
PubMed:
Terpenoids Preserved in Fossils from Miocene-aged Japanese Conifer Wood.
PubMed:
Complete (1)H NMR assignment of cedranolides.
PubMed:
Role of the reaction of stabilized Criegee intermediates with peroxy radicals in particle formation and growth in air.
PubMed:
Gas-phase rate coefficients of the reaction of ozone with four sesquiterpenes at 295 ± 2 K.
PubMed:
In vivo absorption and disposition of α-cedrene, a sesquiterpene constituent of cedarwood oil, in female and male rats.
PubMed:
Coriander (Coriandrum sativum L.) and its bioactive constituents.
PubMed:
Constituents of essential oils from the leaf and flower of Plumeria alba grown in Nigeria.
PubMed:
Role of sterically demanding chiral dirhodium catalysts in site-selective C-H functionalization of activated primary C-H bonds.
PubMed:
Essential oils and crude extracts from Chrysanthemum trifurcatum leaves, stems and roots: chemical composition and antibacterial activity.
PubMed:
Sesquiterpene acids from Shellac and their bioactivities evaluation.
PubMed:
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
PubMed:
GC-MS/MS method for the quantification of α-cedrene in rat plasma and its pharmacokinetic application.
PubMed:
Identification of insecticidal constituents of the essential oil of Acorus calamus rhizomes against Liposcelis bostrychophila Badonnel.
PubMed:
Composition, anticancer, and antimicrobial activities in vitro of the heartwood essential oil of Cunninghamia lanceolata var. konishii from Taiwan.
PubMed:
Pyrolytic formation of polycyclic aromatic hydrocarbons from sesquiterpenes.
PubMed:
Phytochemical analysis of the essential oils of 10 endemic Cephalaria species from Turkey.
PubMed:
Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza.
PubMed:
Determination of gas-phase ozonolysis rate coefficients of a number of sesquiterpenes at elevated temperatures using the relative rate method.
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:
Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill.
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Acaricidal activity against Tetranychus urticae and essential oil composition of four Croton species from Caatinga biome in northeastern Brazil.
PubMed:
Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides.
PubMed:
Chemical composition of the essential oil of Croton gossypiifolius from Venezuela.
PubMed:
Persistency assessment and aerobic biodegradation of selected cyclic sesquiterpenes present in essential oils.
PubMed:
An oxidative dearomatization-induced [5 + 2] cascade enabling the syntheses of α-cedrene, α-pipitzol, and sec-cedrenol.
PubMed:
Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.
PubMed:
[Studies on the chemical constituents of Coleus forskohlii].
PubMed:
Identification of organic hydroperoxides and hydroperoxy acids in secondary organic aerosol formed during the ozonolysis of different monoterpenes and sesquiterpenes by on-line analysis using atmospheric pressure chemical ionization ion trap mass spectrometry.
PubMed:
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
PubMed:
Essential Oil Composition and Antibacterial Studies of Vitex negundo Linn. Extracts.
PubMed:
Contribution to the analysis of the essential oil of Helichrysum italicum (Roth) G. Don. Determination of ester bonded acids and phenols.
PubMed:
Remote position substituents as modulators of conformational and reactive properties of quinones. Relevance of the pi/pi intramolecular interaction.
PubMed:
From alpha-cedrene to crinipellin B and onward: 25 years of the alkene-arene meta-photocycloaddition reaction in natural product synthesis.
PubMed:
New woody and ambery notes from cedarwood and turpentine oil.
PubMed:
Analysis of atmospheric sesquiterpenes: sampling losses and mitigation of ozone interferences.
PubMed:
Aroma evaluation of an aquatic herb, Changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME.
PubMed:
Orientation and feeding responses of the pollen beetle, Meligethes aeneus, to candytuft, Iberis amara.
PubMed:
Volatile sesquiterpene hydrocarbons characteristic for Penicillium roqueforti strains producing PR toxin.
PubMed:
Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes alpha- and beta-cedrene.
PubMed:
Selective oviposition by Aedes aegypti (Diptera: culicidae) in response to Mesocyclops longisetus (Copepoda: Cyclopoidea) under laboratory and field conditions.
PubMed:
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.
PubMed:
Analysis of the essential oil of Juniperus procera Endl. growing in Kenya.
PubMed:
Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain.
PubMed:
The Essential Oil of Perilla ocimoides: A Rich Source of Rosefuran.