L-alpha-fenchyl alcohol
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(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (Click)
CAS Number: 512-13-0
ECHA EINECS - REACH Pre-Reg: 208-135-9
Nikkaji Web: J156.725J
Beilstein Number: 2038083
XlogP3-AA: 2.50 (est)
Molecular Weight: 154.25266000
Formula: C10 H18 O
NMR Predictor: Predict
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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IBM Patents: Obtain
Pubchem Patents: Search
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Physical Properties:
Appearance: white powder (est)
Assay: 98.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.94300 @  25.00 °C.
Refractive Index: 1.46500 @  20.00 °C.
Melting Point: 37.00 to  39.00 °C. @ 760.00 mm Hg
Boiling Point: 202.00 to  203.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.069000 mm/Hg @ 25.00 °C. (est)
Vapor Density: 5.3 ( Air = 1 )
Flash Point: 167.00 °F. TCC ( 75.00 °C. )
logP (o/w): 2.550 (est)
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Organoleptic Properties:
Odor Type: earthy
Odor Strength: medium
 earthy  woody  
Odor Description:
at 100.00 %. 
earthy woody
 clean  cooling  camphoreous  pine  woody  eucalyptus  green  herbal  minty  
Odor Description:
at 1.00 %.  
Clean cooling camphoraceous, piney with a woody eucalyptol and slight green herbal minty nuances
Mosciano, Gerard P&F 25, No. 6, 26, (2000)
 camphoreous  cooling  pine  earthy  minty  citrus  lime  spicy  
Taste Description:
at 1.00 - 5.00 ppm. 
Intense camphoraceous, cooling, piney with an earthy nuance. It has minty-citrus lime and spicy notes
Mosciano, Gerard P&F 25, No. 6, 26, (2000)
Substantivity: 12 Hour(s)
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: perfuming agents
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BOC Sciences
For experimental / research use only.
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavor and fragrance agents
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.
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Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients.View pdf
EPI System: View
Chemicalize.org: Calculate predicted properties
EPA Substance Registry Services (TSCA): 512-13-0
EPA ACToR: Toxicology Data
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0000512130
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NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 512-13-0
Pubchem (cid): 439711
Pubchem (sid): 135267261
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C02344
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2906.19.0000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
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Potential Blenders and core components note
isobornyl formateFL/FR
isobornyl isovalerateFL/FR
isobornyl propionateFL/FR
isobutyl heptanoateFL/FR
isobutyl methyl ketoneFL/FR
2-sec-butyl thiazoleFL/FR
4-butyl thiazoleFL
 melaleuca leucadendron var. cajuputi leaf oilFL/FR
 melaleuca leucadendron cajaputi oilFL/FR
 elettaria cardamomum seed oilFL/FR
 cinnamyl formateFL/FR
ortho-cresyl salicylateFL/FR
 cyperus root oil (cyperus scariosus)FR
 cypress leaf oilFR
 dihydrorose oxideFR
 dimethyl benzyl carbinyl butyrateFL/FR
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetateFL/FR
 ethyl 4-pentenoateFL/FR
 fern absolute 
 fig leaf absoluteFL
 fir needle oil siberiaFL/FR
 galbanum oilFL/FR
 geranium oil africaFL/FR
 geranium oil egyptFL/FR
 germacrene B 
 heptanal (aldehyde C-7)FL/FR
cis-herbal cyclohexaneFR
 herbal dioxaneFR
 herbal norbornaneFR
 herbal undecaneFR
3-hexenyl 2-methyl butyrateFL/FR
 hinoki leaf oilFR
6-hydroxydihydrotheaspirane (mixture of isomers)FL/FR
 hyssop oilFL/FR
english ivy leaf absoluteFR
spike lavender oilFL/FR
spike lavender oil spainFL/FR
 linalool oxideFL/FR
 linalyl formateFL/FR
 marjoram oil (thymus mastichina) spainFL/FR
 niaouli oilFR
 nonisyl formateFR
 oakmoss absoluteFL/FR
1-octen-3-yl acetateFL/FR
 origanum oil greeceFL/FR
 origanum oilFL/FR
 orris hexanoneFR
2-pentyl cyclopentanoneFR
 petitgrain combava oilFR
 pine hexanolFR
2-propyl thiazoleFL
 rose pyranFR
 sabinene hydrateFL/FR
 sage oil dalmatianFL/FR
 seaweed absolute (fucus vesiculosus et serratus)FL/FR
 tagete oil CO2 extractFL/FR
 tagete oil rwandaFL/FR
 tagete oil south africaFL/FR
 tropical indeneFR
 turmeric oleoresinFL
 vetiver oil haitiFL/FR
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Potential Uses:
 earth humusFR
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Natural Occurrence in: note
 boldo leaf oil italy @ 0.40%
Data  GC  GRIN Trop Picture
 boldus leaf oil chile @ 0.22%
Data  GC  GRIN Trop Picture
 carrot weed oil @ 0.76%
Data  GC  GRIN Trop Picture
 cascarilla bark oil @ 0.01%
Data  GC  GRIN Trop Picture
 cypress cone oil egypt @ 0.2%
Data  GC  GRIN Trop Picture
 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 0.20%
Data  GC  GRIN Trop Picture
 eucalyptus dalrympleana maiden leaf oil ethiopia @ 3.10%
Data  GC  GRIN Trop Picture
 eucalyptus delegatensis r. baker leaf oil ethiopia @ 0.80%
Data  GC  GRIN Trop Picture
 eucalyptus globulus maidenii f. muell oil @ 0.07%
Data  GC  GRIN Trop Picture
 eucalyptus globulus pseudoglobulus oil @ 0.10%
Data  GC  GRIN Trop Picture
 eucalyptus grandis w. hill ex maiden leaf oil ethiopia @ 0.60%
Data  GC  GRIN Trop Picture
 eucalyptus urophylla s.t. blake leaf oil ethiopia @ 0.70%
Data  GC  GRIN Trop Picture
 hinoki leaf oil @ 2.09%
Data  GC  GRIN Trop Picture
 hinoki root oil @ 0.71%
Data  GC  GRIN Trop Picture
 hinoki wood oil @ 0.42%
Data  GC  GRIN Trop Picture
 hypericum dogonbadanicum assadi oil iran @ 0.70%
Data  GC  GRIN Trop Picture
 lemongrass oil morocco @ 0.10%
Data  GC  GRIN Trop Picture
 lime oil distilled mexico @ 0.79%
Data  GC  GRIN Trop Picture
 lime oil distilled peru @ 0.82%
Data  GC  GRIN Trop Picture
 marjoram oil sweet morocco @ 1.68%
Data  GC  GRIN Trop Picture
 mastic fruit oil @ 0.58%
Data  GC  GRIN Trop Picture
 mastic leaf oil @ 0.14%
Data  GC  GRIN Trop Picture
 pine needle oil scotch siberia @ 0.1-0.2%
Data  GC  GRIN Trop Picture
 plectranthus glandulosus hook f. leaf oil cameroon @ 1.50%
Data  GC  GRIN Trop Picture
 pteronia oil @ 0.10%
Data  GC  GRIN Trop Picture
 thyme oil wild or creeping pakistan @ 0.91%
Data  GC  GRIN Trop Picture
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 bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)-
2-norbornanol, 1,3,3-trimethyl-, (-)-endo-
(-)-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
1,3,3-trimethyl-2-norbornanol, (1S-endo)-
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PubMed: Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl).
PubMed: Fragrance material review on fenchyl alcohol.
PubMed: Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes.
PubMed: Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol.
PubMed: Biosynthesis of monoterpenes. Stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (-)-endo-fenchol.
PubMed: Monoterpene biosynthesis: mechanistic evaluation of the geranyl pyrophosphate:(-)-endo-fenchol cyclase from fennel (Foeniculum vulgare).
PubMed: Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil.
PubMed: Chemical analysis and biological activity of the essential oils of two endemic Soqotri Commiphora species.
PubMed: Inhibitory effects of monoterpenes on human TRPA1 and the structural basis of their activity.
PubMed: 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).
PubMed: 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.
PubMed: A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.
PubMed: Antioxidant and antimicrobial properties of the essential oil and extracts of Zanthoxylum alatum grown in north-western Himalaya.
PubMed: Phosphinofenchol or metastable phosphorane? Phosphorus derivatives of fenchol.
PubMed: [GC-MS analysis of chemical components in seeds oil from Croton tiglium].
PubMed: Distillation time effect on lavender essential oil yield and composition.
PubMed: Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
PubMed: GC and GC/MS analysis of essential oil composition of the endemic Soqotraen Leucas virgata Balf.f. and its antimicrobial and antioxidant activities.
PubMed: Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults.
PubMed: Fumigant toxicity and oviposition deterrency of the essential oil from cardamom, Elettaria cardamomum, against three stored–product insects.
PubMed: Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris.
PubMed: Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.
PubMed: Effects of the origins of Botrytis cinerea on earthy aromas from grape broth media further inoculated with Penicillium expansum.
PubMed: Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia).
PubMed: Microextraction and Gas Chromatography/Mass Spectrometry for improved analysis of geosmin and other fungal "off" volatiles in grape juice.
PubMed: Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India.
PubMed: Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity.
PubMed: Compositional variability in essential oil from different parts of Alpinia speciosa from India.
PubMed: NIR-VCD, vibrational circular dichroism in the near-infrared: experiments, theory and calculations.
PubMed: Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics.
PubMed: Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus Brevicomis LeConte (Coleoptera: Scolytidae).
PubMed: Odor thresholds of microbially induced off-flavor compounds in apple juice.
PubMed: Phytochemical investigation and evaluation of anti-inflammatory and anti-arthritic activities of essential oil of Strobilanthus ixiocephala Benth.
PubMed: Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.
PubMed: Monoterpenes as drug shuttles: cytotoxic (6-aminomethylnicotinate)dichloridoplatinum(II) complexes with potential to overcome cisplatin resistance.
PubMed: Determination of essential oil components of Artemisia haussknechtii Boiss. using simultaneous hydrodistillation-static headspace liquid phase microextraction-gas chromatography mass spectrometry.
PubMed: Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia.
PubMed: Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
PubMed: Olfactory discrimination of structurally related molecules: receptor cell responses to camphoraceous odorants.
PubMed: Sensitive indoor air monitoring of monoterpenes using different adsorbents and thermal desorption gas chromatography with mass-selective detection.
PubMed: Rationalization of enantioselectivities in dialkylzinc additions to benzaldehyde catalyzed by fenchone derivatives.
PubMed: Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
PubMed: [GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].
PubMed: 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.
PubMed: A dispensable methoxy group? Phenyl fencholate as a chiral modifier of n-butyllithium.
PubMed: Relationships between odor-elicited oscillations in the salamander olfactory epithelium and olfactory bulb.
PubMed: Characterisation of volatile organic compounds in stemwood using solid-phase microextraction.
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Soluble in:
 water, 461.4 mg/L @ 25 °C (est)
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