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(-)-alpha-fenchol

Chemical Structure

General Material Information

Preferred name (-)-alpha-fenchol
Trivial Name (-)-α-Fenchol
Short Description L-alpha-fenchyl alcohol
Formula C10 H18 O
CAS Number 512-13-0
ECHA Number 208-135-9
FDA UNII UJ108AQX3M
Nikkaji Number J156.725J
Beilstein Number 2038083
xLogP3-AA 2.50 (est)
NMR Predictor External link
Synonyms
  • bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)-
  • 2-nor bornanol, 1,3,3-trimethyl-, (-)-endo-
  • (-)-alpha- fenchol
  • (-)-alpha- fenchyl alcohol
  • L-alpha- fenchyl alcohol
  • laevo-alpha- fenchyl alcohol
  • trimethyl bicyclo-2-heptanol
  • (1S-endo)-1,3,3-trimethyl bicyclo(2.2.1)heptan-2-ol
  • (1S,2S,4R)-1,3,3-trimethyl bicyclo(2.2.1)heptan-2-ol
  • (1S-endo)-1,3,3-trimethyl-2-norbornanol
  • 1,3,3-trimethyl-2-norbornanol, (1S-endo)-
  • (1S-endo)-1,3,3-trimethylbicyclo(2.2.1)heptan-2-ol
  • (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  • (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  • Bicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethyl-, (1S,2S,4R)-
  • Bicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)-
  • (-)-endo-Fenchol
  • (-)-α-Fenchol
  • l-α-Fenchyl alcohol
  • (1S-endo)-Fenchol
  • (1S,2S,4R)-endo-Fenchol
  • (1R)-endo-(+)-Fenchyl alcohol

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Literature & References

(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:512-13-0
Pubchem (cid):439711
Pubchem (sid):135267261
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).
Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil.
Chemical analysis and biological activity of the essential oils of two endemic Soqotri Commiphora species.
Inhibitory effects of monoterpenes on human TRPA1 and the structural basis of their activity.
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.
[GC-MS analysis of chemical components in seeds oil from Croton tiglium].
Distillation time effect on lavender essential oil yield and composition.
Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
GC and GC/MS analysis of essential oil composition of the endemic Soqotraen Leucas virgata Balf.f. and its antimicrobial and antioxidant activities.
Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults.
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.
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.
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.
Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity.
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.
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.
Phytochemical investigation and evaluation of anti-inflammatory and anti-arthritic activities of essential oil of Strobilanthus ixiocephala Benth.
Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.
Monoterpenes as drug shuttles: cytotoxic (6-aminomethylnicotinate)dichloridoplatinum(II) complexes with potential to overcome cisplatin resistance.
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.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
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.
Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
[GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].
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.

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
CHEBI:View
KEGG (GenomeNet):C02344
HMDB (The Human Metabolome Database):Search
FooDB:FDB005916
Export Tariff Code:2906.19.0000
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 154.2526550293
Specific gravity @ 25 °C
Pounds per Gallon
Melting Point 37 to 39°C @ 760 mm Hg
Boiling Point 202 to 203°C @ 760 mm Hg
Vapor Pressure 0.069 mmHg @ 25 °C
Vapor Density 5.3
Flash Point TCC Value 75 °C TCC
logP (o/w) 2.55 est
Solubility
alcohol Yes
water, 461.4 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Earthy
earthy, woody, clean, cooling, camphoreous, pine, eucalyptus, green, herbal, minty
Odor strength medium
Substantivity 12 hour(s) at 100.00 %
General comment At 100.00 %. earthy woody
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 1.00 %. Clean cooling camphoraceous, piney with a woody eucalyptol and slight green herbal minty nuances
Flavor Type: Camphoreous
camphoreous, cooling, pine, earthy, minty, citrus, lime, spicy
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 1.00 - 5.00 ppm. Intense camphoraceous, cooling, piney with an earthy nuance. It has minty-citrus lime and spicy notes

Occurrences

Potential Uses

Applications
Odor purposes Blueberry, Citrus, Earth, Herbal, Lime, Spice, Strawberry, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 38 - Irritating to skin.
S 02 - Keep out of the reach of children.
S 24 - Avoid contact with skin.
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.
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
Recommendation for (-)-alpha-fenchol usage levels up to:
8.0000 % in the fragrance concentrate.
Recommendation for (-)-alpha-fenchol flavor usage levels up to:
5.0000 ppm in the finished product.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):512-13-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :439711
National Institute of Allergy and Infectious Diseases:Data
(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Chemidplus:0000512130