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General Material Information

Preferred name fenchol
Trivial Name Fenchol
Short Description fenchyl alcohol
Formula C10 H18 O
CAS Number 1632-73-1
Deleted CAS Number 10378-33-3
FEMA Number 2480
Flavis Number 2.038
ECHA Number 216-639-5
FDA UNII 410Q2GK1HF
Nikkaji Number J7.537J
MDL MFCD00003760
COE Number 87
xLogP3-AA 2.50 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1397 fenchyl alcohol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 1632-73-1 ; FENCHYL ALCOHOL
Synonyms
  • bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-
  • bicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethyl-
  • 2-nor bornanol, 1,3,3-trimethyl-
  • 3,3-dimethyl-8,9-dinorbornan-2-ol
  • 2-fenchanol
  • fenchyl alcohol
  • alpha- fenchyl alcohol
  • fenchyl alcohol natural
  • 1,3,3-trimethyl bicyclo(2.2.1)heptan-2-ol
  • 1,3,3-trimethyl-2-norbornanol
  • 1,3,3-trimethyl-bicyclo(2.2.1)heptan-2-ol
  • 1,3,3-trimethylbicyclo(2.2.1)heptan-2-ol
  • 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  • 1,5,5-trimethylbicyclo[2.2.1]heptan-6-ol
  • 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  • 2-Norbornanol, 1,3,3-trimethyl-
  • 2-Fenchanol
  • 1,3,3-Trimethyl-2-norbornanol
  • 2,2,4-Trimethylbicyclo[2.2.1]heptan-3-ol

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

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Literature & References

1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1632-73-1
Pubchem (cid):15406
Pubchem (sid):135020028
Flavornet:1632-73-1
Pherobase:View
Publications by PubMed
Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl).
Fragrance material review on fenchyl alcohol.
Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes.
Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol.
Biosynthesis of monoterpenes. Stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (-)-endo-fenchol.
Monoterpene biosynthesis: mechanistic evaluation of the geranyl pyrophosphate:(-)-endo-fenchol cyclase from fennel (Foeniculum vulgare).
Biosynthesis of monoterpenes: conversion of the acyclic precursors geranyl pyrophosphate and neryl pyrophosphate to the rearranged monoterpenes fenchol and fenchone by a soluble enzyme preparation from fennel (Foeniculum vulgare).
Biosynthesis of monoterpenes: preliminary characterization of i-endo-fenchol synthetase from fennel (Foeniculum vulgare) and evidence that no free intermediate is involved in the cyclization of geranyl pyrophosphate to the rearranged product.
A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.
Antioxidant and antimicrobial properties of the essential oil and extracts of Zanthoxylum alatum grown in north-western Himalaya.
Phosphinofenchol or metastable phosphorane? Phosphorus derivatives of fenchol.
Distillation time effect on lavender essential oil yield and composition.
Inhibitory effects of monoterpenes on human TRPA1 and the structural basis of their activity.
GC and GC/MS analysis of essential oil composition of the endemic Soqotraen Leucas virgata Balf.f. and its antimicrobial and antioxidant activities.
Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil.
Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults.
[GC-MS analysis of chemical components in seeds oil from Croton tiglium].
Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.
Effects of the origins of Botrytis cinerea on earthy aromas from grape broth media further inoculated with Penicillium expansum.
Fumigant toxicity and oviposition deterrency of the essential oil from cardamom, Elettaria cardamomum, against three stored–product insects.
Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris.
Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia).
Microextraction and Gas Chromatography/Mass Spectrometry for improved analysis of geosmin and other fungal "off" volatiles in grape juice.
Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India.
Chemical analysis and biological activity of the essential oils of two endemic Soqotri Commiphora species.
Compositional variability in essential oil from different parts of Alpinia speciosa from India.
NIR-VCD, vibrational circular dichroism in the near-infrared: experiments, theory and calculations.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics.
Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus Brevicomis LeConte (Coleoptera: Scolytidae).
Odor thresholds of microbially induced off-flavor compounds in apple juice.
Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
Determination of essential oil components of Artemisia haussknechtii Boiss. using simultaneous hydrodistillation-static headspace liquid phase microextraction-gas chromatography mass spectrometry.
Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia.
Olfactory discrimination of structurally related molecules: receptor cell responses to camphoraceous odorants.
Sensitive indoor air monitoring of monoterpenes using different adsorbents and thermal desorption gas chromatography with mass-selective detection.
Rationalization of enantioselectivities in dialkylzinc additions to benzaldehyde catalyzed by fenchone derivatives.
Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity.
Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine.
A dispensable methoxy group? Phenyl fencholate as a chiral modifier of n-butyllithium.
Relationships between odor-elicited oscillations in the salamander olfactory epithelium and olfactory bulb.
Characterisation of volatile organic compounds in stemwood using solid-phase microextraction.
[GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].

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
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C02344
HMDB (The Human Metabolome Database):HMDB34932
FooDB:FDB013522
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 154.2526550293
Melting Point 35 to 40°C @ 760 mm Hg
Boiling Point 201 to 202°C @ 760 mm Hg
Boiling Point 122 to 123°C @ 50 mm Hg
Vapor Pressure 0.069 mmHg @ 25 °C
Flash Point TCC Value 73.89 °C TCC
logP (o/w) 2.55 est
Solubility
alcohol Yes
water, 461.4 mg/L @ 25 °C (est) Yes
water No
Stability
alcoholic fine fragrance Good
fabric softener Good
liquid detergent Good
perborate powder detergent Good
soap Good
toiletry application Good
antiperspirant Fair
hypochlorite bleach Fair

Organoleptic Properties

Odor Type: Camphoreous
camphoreous, pine, woody, dry, rooty, sweet, lemon
Odor strength medium
Substantivity 12 hour(s) at 100.00 %
Luebke, William tgsc, (1989) At 100.00 %. camphor borneol pine woody dry sweet lemon
Flavor Type: Camphoreous
camphoreous, cooling, medicinal, minty, earthy, humus
Luebke, William tgsc, (1989) Camphoreous cooling medicinal minty earthy humus
General comment Fresh, pine

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
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:
4 % 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
maximum skin levels for fine fragrances:
0.0600 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2004)
Recommendation for fenchol usage levels up to:
4.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.0500 %
Dermal Systemic Exposure in Cosmetic Products:
0.0013 mg/kg/day (IFRA, 2004)
Maximised Survey-derived Daily Intakes (MSDI-EU): 55.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 17.00 (μg/capita/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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -0.25000
beverages(nonalcoholic): -1.80000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.25000
fruit ices: -0.25000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -4.70000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

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 47, (FGE.47)[1] - Bicyclic secondary alcohols, ketones and related esters from chemical group 8 - 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 87, (FGE.87)[1] - Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47 (2008) - 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 43: Thujyl alcohol from chemical group 8
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87 Revision 1 (FGE.87Rev1): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008)
View page or View pdf

Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species
View page or View pdf

EPI System: View
EPA Substance Registry Services (TSCA):1632-73-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :15406
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1325
WGK Germany:2
1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Chemidplus:0001632731