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cedrol

Chemical Structure

General Material Information

Preferred name cedrol
Trivial Name (+)-Cedrol
Short Description (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol
Formula C15 H26 O
CAS Number 77-53-2
Deleted CAS Number 13567-37-8
FEMA Number 4503
Flavis Number 2.12
ECHA Number 201-035-6
FDA UNII 63ZM9703BO
Nikkaji Number J499.451E
Beilstein Number 2206347
MDL MFCD00062952
COE Number 10190
xLogP3-AA 3.90 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 2030 (+)-cedrol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 77-53-2 ; (+)-CEDROL
Synonyms
  • cedar camphor
  • (8a)- cedran-8-ol
  • (8R)- cedran-8-ol
  • 8-betaH- cedran-8-ol
  • 8betaH- cedran-8-ol
  • 8bH- cedran-8-ol
  • a- cedrol
  • cedrol 35% natural
  • cedrol 60% natural
  • cedrol crystals
  • cedrol crystals nat.
  • cedrol crystals natural
  • cedrol liquid (55-60% cedrol)
  • cedrol powder natural
  • cedrol prime (45-50% cedrol)
  • cedrol redistilled texas
  • cypress camphor
  • 1H-3a,7-methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-
  • (3R-(3alpha,3abeta, 6alpha,7beta,8aalpha))- octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • (3R,3aS, 6R,7R,8aS)- octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • [3R-(3a,3ab,6a,7b,8aa)]- octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • [3R-(3a,3aβ,6a,7β,8aa)]- octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • (1S,2R,5R,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0]undecan-8-ol
  • (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol
  • (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01.5]undecan-8-ol
  • (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol
  • 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-
  • 8βH-Cedran-8-ol
  • 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, [3R-(3α,3aβ,6α,7β,8aα)]-
  • (3R,3aS,6R,7R,8aS)-Octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • α-Cedrol
  • (+)-Cedrol
  • Cedrol Nanomedicin
  • (3R,3AS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-ol

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

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Literature & References

(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:77-53-2
Pubchem (cid):65575
Pubchem (sid):135022674
Pherobase:View
Publications by PubMed
Anticholinesterase and β-Site Amyloid Precursor Protein Cleaving Enzyme 1 Inhibitory Compounds from the Heartwood of Juniperus chinensis.
Complete (1)H NMR assignment of cedranolides.
Discovery of an oviposition attractant for gravid malaria vectors of the Anopheles gambiae species complex.
Chemical Constituents from Sinningia canescens and S. warmingii.
Essential oil from the heartwood of Taiwan fir ameliorates LPS-induced inflammatory response by inhibiting the activation of mitogen-activated protein kinase.
Inhibitory effects of cedrol, β-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes.
Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mites.
Chemical composition and antimicrobial activity of the essential oil of Juniperus excelsa M.Bieb. growing wild in Lebanon.
Bioactivity of cedarwood oil and cedrol against arthropod pests.
Differential transcriptome analysis of glandular and filamentous trichomes in Artemisia annua.
Studies on the expression of linalool synthase using a promoter-β-glucuronidase fusion in transgenic Artemisia annua.
Studies on the expression of sesquiterpene synthases using promoter-β-glucuronidase fusions in transgenic Artemisia annua L.
Essential-oil composition of the Tunisian endemic cypress (Cupressus sempervirens L. var. numidica TRAB.).
Profiling of volatile compounds of Phyllostachys pubescens shoots in Taiwan.
Chemical constituents of volatile oil from Pyrolae herba and antiproliferative activity against SW1353 human chondrosarcoma cells.
Platelet-activating factor (PAF)-antagonists of natural origin.
Composition, anticancer, and antimicrobial activities in vitro of the heartwood essential oil of Cunninghamia lanceolata var. konishii from Taiwan.
The potential of Cyathus africanus for transformation of terpene substrates.
Structure based virtual screening of novel inhibitors against multidrug resistant superbugs.
Functional expression and characterization of sesquiterpene synthases from Artemisia annua L. using transient expression system in Nicotiana benthamiana.
[Analyze on chemical compositions of Dalbergia odorifera essential oils extracted by CO2-supercritical-fluid-extraction and steam distillation extraction].
Chemical composition of volatile oils from the pericarps of Indian sandalwood (Santalum album) by different extraction methods.
[GC-MS analysis on volatile components of wild Trogopterus faeces from Laishui county of Hebei province].
Cedrol Enhances Extracellular Matrix Production in Dermal Fibroblasts in a MAPK-Dependent Manner.
Effects of direct cedrol inhalation into the lower airway on brain hemodynamics in totally laryngectomized subjects.
In vitro Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated from Thujopsis dolabrata.
Chiral recognition of diastereomeric 6-cedrols by vibrational circular dichroism.
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.
Phytochemicals from Cunninghamia konishii Hayata act as antifungal agents.
Inhibitory effect of compounds from Goniothalamus tapis Miq. and Goniothalamus uvaroides King on platelet-activating factor receptor binding.
Chemical analysis of incense smokes used in Shaxi, Southwest China: a novel methodological approach in ethnobotany.
Volatile constituents, inorganic elements and primary screening of bioactivity of black coral cigarette holders.
Isolation, chemical, and biotransformation routes of labdane-type diterpenes.
Relative expression of genes of terpene metabolism in different tissues of Artemisia annua L.
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.
Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation.
Antiplatelet aggregation and platelet activating factor (PAF) receptor antagonistic activities of the essential oils of five Goniothalamus species.
Relation between developmental stage, sensory properties, and volatile content of organically and conventionally grown pac choi (Brassica rapa var. Mei Qing Choi).
Immunotoxicity activity of the major essential oils of Valeriana fauriei Briq against Aedes aegypti L.
Biotransformation of alpha-cedrol and caryophyllene oxide by the fungus Neurospora crassa.
[Electroantennogram responses of Maruca testulalis (Lepidoptera: Pyralidae) to plant volatiles and sex pheromone].
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.
Antiproliferative effects of essential oils and their major constituents in human renal adenocarcinoma and amelanotic melanoma cells.
A new labdane-type diterpene from the bark of Juniperus chinensis Linn.
A gold-catalyzed entry into the sesquisabinene and sesquithujene families of terpenoids and formal total syntheses of cedrene and cedrol.
Fragrance material review on cedrol.
Woody pretzels: spirocycles from vetiver to patchouli and Georgywood.
Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya.
[Advances in sesquiterpene synthases cyclases of Artemisia annua].
Effects of direct cedrol inhalation into the lower airway on autonomic nervous activity in totally laryngectomized subjects.
Antimicrobial activity of extractable conifer heartwood compounds toward Phytophthora ramorum.
Eudismic analysis of tricyclic sesquiterpenoid alcohols: lead structures for the design of potent inhibitors of the human UDP-glucuronosyltransferase 2B7.
Overseas survey of the effect of cedrol on the autonomic nervous system in three countries.
Sesquiterpenes from the wood of Juniperus lucayana.
Chemical composition, cytotoxic activity and antimicrobial activity of essential oils of leaves and berries of Juniperus phoenicea L. grown in Egypt.
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
[Chemical components and antimicrobial activity of essential oils in Cunninghamia lanceolata heartwood].
[Studies on the chemical constituents in root of Coleus forskohlii].
Reduction of infectivity of schistosome cercariae by application of cercaricidal oil to water.
[Terpenoids in root exudates of different allelopathic rice varieties].
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
Intramolecular iron-mediated diene/olefin cyclocoupling: formation of carbon spirocycles.
Pressurized fluids for extraction of cedarwood oil from Juniperus virginianna.
New terpenoids in cultivated and wild chamomile (in vivo and in vitro).
Autonomic responses during inhalation of natural fragrance of Cedrol in humans.
Stereospecific hydroxylation of (+)-cedrol by using human skin microbial flora Staphylococcus epidermidis.
The sedative effects and mechanism of action of cedrol inhalation with behavioral pharmacological evaluation.
Crystal structure of 1beta-hydroxy-beta-homopipitzolone (9-hydroxy-2,6,9-trimethyltricyclo[6,3,1,0(1,6)]dodeca-5,10,11,12-tetraone).
Metabolic engineering to produce sesquiterpenes in yeast.
Volatile constituents of the fruit and leaf oils of Thuja orientalis L. grown in Iran.
[Analysis of chemical constituents in the essential oil from Evodia fargesii by GC/MS].
Antimicrobial activity of some Pacific Northwest woods against anaerobic bacteria and yeast.
[Studies on the chemical components from Sargassum fusiform].
Antitermitic activity of essential oils and components from Taiwania (Taiwania cryptomerioides).
Biotransformation of cedrol by Curvularia lunata ATCC 12017.
Potential antitermite compounds from Juniperus procera extracts.
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.
The molecular cloning of 8-epicedrol synthase from Artemisia annua.
Analysis of the essential oil of Juniperus procera Endl. growing in Kenya.
Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis.
Phylogenetic influences in microbial hydroxylation of terpenoids.
Schistosoma mansoni: cercaricidal effects of cedarwood oil and various of its components.
GLC-mass spectrometry of Teucrium polium oil.
Exposure to an environment containing the aromatic red cedar, Juniperus virginiana: procarcinogenic, enzyme-inducing and insecticidal effects.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09631
HMDB (The Human Metabolome Database):Search
FooDB:FDB014697
Export Tariff Code:2906.19.3000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
FAO:(+)-Cedrol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Melting Point 77 to 86°C @ 760 mm Hg
Boiling Point 285 to 287°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 81.11 °C TCC
logP (o/w) 4.33
Solubility
alcohol Yes
water, 21.88 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Woody
cedarwood, woody, dry, sweet
Odor strength low
Substantivity 400 hour(s) at 20.00 % in dipropylene glycol
Luebke, William tgsc, (1993) At 100.00 %. cedarwood woody dry sweet soft
Flavor Type: Woody
woody, amber, floral, cedar, ambrette, musk, powdery
Luebke, William tgsc, (1993) Woody amber floral cedar ambrette musk powdery
General comment Soft woody, cedarwood-like

Occurrences

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 24/25 - Avoid contact with skin and eyes.
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:
8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD > 500 mg/kg
"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 8, Pg. 102, 1956.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 745, 1975.

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
Recommendation for cedrol usage levels up to:
50.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 13.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3900 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 24
Click here to view publication 24
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 5.0000025.00000
beverages(alcoholic): 5.0000025.00000
breakfast cereal: 5.0000025.00000
cheese: 7.0000035.00000
chewing gum: --
condiments / relishes: 20.00000100.00000
confectionery froastings: 10.0000050.00000
egg products: --
fats / oils: 5.0000025.00000
fish products: 2.0000010.00000
frozen dairy: 7.0000035.00000
fruit ices: 10.0000050.00000
gelatins / puddings: 10.0000050.00000
granulated sugar: --
gravies: 5.0000025.00000
hard candy: 10.0000050.00000
imitation dairy: 7.0000035.00000
instant coffee / tea: 5.0000025.00000
jams / jellies: 7.0000035.00000
meat products: 2.0000010.00000
milk products: 7.0000035.00000
nut products: 5.0000025.00000
other grains: 5.0000025.00000
poultry: 2.0000010.00000
processed fruits: 7.0000035.00000
processed vegetables: 7.0000035.00000
reconstituted vegetables: 7.0000035.00000
seasonings / flavors: 5.0000025.00000
snack foods: 10.0000050.00000
soft candy: 10.0000050.00000
soups: 5.0000025.00000
sugar substitutes: --
sweet sauces: 5.0000025.00000
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 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 90 (FGE.90): Consideration of Aliphatic, acyclic and alicyclic terpenoid tertiary alcohols and structurally related substances evaluated by JECFA (68th meeting)FGE.18Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 2 (FGE.18Rev2): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 3 (FGE.18Rev3): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):77-53-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65575
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol
Chemidplus:0000077532
RTECS:PB7728666 for cas# 77-53-2