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alpha-cedrene

Chemical Structure

General Material Information

Preferred name alpha-cedrene
Trivial Name (-)-Cedrene
Short Description (1S,2R,5S)-2,6,6,8-tetramethyl tricyclo(5.3.1.01.5)undec-8-ene
Formula C15 H24
CAS Number 469-61-4
Deleted CAS Number 1224161-35-6
ECHA Number 207-418-4
FDA UNII 50D4A81G8T
Beilstein Number 3196861
MDL MFCD00063003
COE Number 10985
xLogP3-AA 4.60 (est)
NMR Predictor External link
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
  • (3R-(3a,3ab,7b,8aa))-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)-
  • Cedr-8-ene
  • α-Cedrene
  • 1H-3a,7-Methanoazulene, 2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-, [3R-(3α,3aβ,7β,8aα)]-
  • (3R,3aS,7S,8aS)-2,3,4,7,8,8a-Hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene
  • Levo-α-cedrene
  • (-)-α-Cedrene
  • (-)-Cedrene
  • [3R-(3α,3aβ,7β,8αa)]-2,3,4,7,8,8a-Hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(3R-(3a,3ab,7b,8aa))-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:469-61-4
Pubchem (cid):10099
Pubchem (sid):134975160
Pherobase:View
Publications by PubMed
[Analysis of Volatile Oils from Different Processed Products of Zingiber officinale Rhizome by GC-MS].
Metabolite Profiling and Comparison of Bioactivity in Antrodia cinnamomea and Antrodia salmonea Fruiting Bodies.
Terpenoids Preserved in Fossils from Miocene-aged Japanese Conifer Wood.
Complete (1)H NMR assignment of cedranolides.
Role of the reaction of stabilized Criegee intermediates with peroxy radicals in particle formation and growth in air.
Gas-phase rate coefficients of the reaction of ozone with four sesquiterpenes at 295 ± 2 K.
In vivo absorption and disposition of α-cedrene, a sesquiterpene constituent of cedarwood oil, in female and male rats.
Coriander (Coriandrum sativum L.) and its bioactive constituents.
Constituents of essential oils from the leaf and flower of Plumeria alba grown in Nigeria.
Role of sterically demanding chiral dirhodium catalysts in site-selective C-H functionalization of activated primary C-H bonds.
Essential oils and crude extracts from Chrysanthemum trifurcatum leaves, stems and roots: chemical composition and antibacterial activity.
Sesquiterpene acids from Shellac and their bioactivities evaluation.
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
GC-MS/MS method for the quantification of α-cedrene in rat plasma and its pharmacokinetic application.
Identification of insecticidal constituents of the essential oil of Acorus calamus rhizomes against Liposcelis bostrychophila Badonnel.
Composition, anticancer, and antimicrobial activities in vitro of the heartwood essential oil of Cunninghamia lanceolata var. konishii from Taiwan.
Pyrolytic formation of polycyclic aromatic hydrocarbons from sesquiterpenes.
Phytochemical analysis of the essential oils of 10 endemic Cephalaria species from Turkey.
Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza.
Determination of gas-phase ozonolysis rate coefficients of a number of sesquiterpenes at elevated temperatures using the relative rate method.
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.
Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill.
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
Acaricidal activity against Tetranychus urticae and essential oil composition of four Croton species from Caatinga biome in northeastern Brazil.
Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides.
Chemical composition of the essential oil of Croton gossypiifolius from Venezuela.
Persistency assessment and aerobic biodegradation of selected cyclic sesquiterpenes present in essential oils.
An oxidative dearomatization-induced [5 + 2] cascade enabling the syntheses of α-cedrene, α-pipitzol, and sec-cedrenol.
Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.
[Studies on the chemical constituents of Coleus forskohlii].
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.
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
Essential Oil Composition and Antibacterial Studies of Vitex negundo Linn. Extracts.
Contribution to the analysis of the essential oil of Helichrysum italicum (Roth) G. Don. Determination of ester bonded acids and phenols.
Remote position substituents as modulators of conformational and reactive properties of quinones. Relevance of the pi/pi intramolecular interaction.
From alpha-cedrene to crinipellin B and onward: 25 years of the alkene-arene meta-photocycloaddition reaction in natural product synthesis.
New woody and ambery notes from cedarwood and turpentine oil.
Analysis of atmospheric sesquiterpenes: sampling losses and mitigation of ozone interferences.
Aroma evaluation of an aquatic herb, Changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME.
Orientation and feeding responses of the pollen beetle, Meligethes aeneus, to candytuft, Iberis amara.
Volatile sesquiterpene hydrocarbons characteristic for Penicillium roqueforti strains producing PR toxin.
Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes alpha- and beta-cedrene.
Selective oviposition by Aedes aegypti (Diptera: culicidae) in response to Mesocyclops longisetus (Copepoda: Cyclopoidea) under laboratory and field conditions.
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.
Analysis of the essential oil of Juniperus procera Endl. growing in Kenya.
Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain.
The Essential Oil of Perilla ocimoides: A Rich Source of Rosefuran.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C09630
HMDB (The Human Metabolome Database):Search
FooDB:FDB003904
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 204.35627746582
Specific gravity @ 25 °C
Pounds per Gallon 7.705 to 7.797
Refractive Index 1.5 to 1.503 @ 20 °C
Boiling Point 261 to 262°C @ 760 mm Hg
Vapor Pressure 0.018 mmHg @ 25 °C
Flash Point TCC Value 103.89 °C TCC
logP (o/w) 6.308 est
Solubility
alcohol Yes
water, 0.1504 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Woody
woody, cedar, sweet, fresh
Odor strength medium
Substantivity 112 hour(s) at 100.00 %
Luebke, William tgsc, (1987) At 100.00 %. woody cedar sweet fresh

Occurrences

Potential Uses

Applications
Odor purposes Balsam, Cedar, Cedarwood, Clary sage oil replacer, Costus, Herbal, Juniper, Lavender, Sandalwood, Sassafras, Woody
Other purposes Topnotes
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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.
Human Experience:
5 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Dermal sensitization
View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.27 %
Category 2: Products applied to the axillae
0.080 %
Category 3: Products applied to the face/body using fingertips
1.60 %
Category 4: Products related to fine fragrance
1.50 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.38 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.38 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.38 %
Category 5D: Baby Creams, baby Oils and baby talc
0.38 %
Category 6: Products with oral and lip exposure
0.88 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
3.10 %
Category 7B: Leave-on products applied to the hair with some hand contact
3.10 %
Category 8: Products with significant anogenital exposure
0.16 %
Category 9: Products with body and hand exposure, primarily rinse off
2.90 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
11.00 %
Category 10B: Household aerosol/spray products
11.00 %
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
5.80 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
5.80 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
No Restriction
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

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
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 25, (FGE.25)[1] - Aliphatic and aromatic hydrocarbons from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the Panel on Food Additives,Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Scientific opinion on Flavouring Group Evaluation 25, Revision 3 (FGE.25Rev3): Aliphatic hydrocarbons from chemical group 31
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):469-61-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10099
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3082
WGK Germany:2
(3R-(3a,3ab,7b,8aa))-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene
Chemidplus:0000469614
RTECS:PB7725000 for cas# 469-61-4