(-)-alpha-fenchol
 
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(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (Click)
CAS Number: 512-13-0
ECHA EC Number:208-135-9
FDA UNII:UJ108AQX3M
Beilstein Number:2038083
FEMA Number:2480
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
FEMA Number:2480  L-alpha-fenchyl alcohol
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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
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Organoleptic Properties:
Odor Type:earthy
Odor Strength:medium
Odor Description:
at 100.00 %. 
earthy woody
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)
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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Suppliers:
BOC Sciences
(1S,2S,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol
For experimental / research use only.
Parchem
(-)-alpha-Fenchol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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Safety Information:
Most important hazard(s):
Xi - Irritant
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:
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
 (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Chemidplus:0000512130
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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
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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
CHEBI:View
Export Tariff Code:2906.19.0000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
2-acetoxy-1,8-cineoleFL
dextro-borneolFL/FR
isobornyl formateFL/FR
isobornyl isovalerateFL/FR
isobornyl propionateFL/FR
isobutyl heptanoateFL/FR
isobutyl methyl ketoneFL/FR
2-sec-butyl thiazoleFL/FR
4-butyl thiazoleFL
 cajuput leaf oilFL/FR
 cajuput oilFL/FR
 cardamom seed oilFL/FR
4-carvomenthenolFL/FR
1,8-cineoleFL/FR
 cinnamyl formateFL/FR
ortho-cresyl salicylateFL/FR
 cuminaldehydeFL/FR
isocyclocitralFL/FR
 cyperus root oil (cyperus scariosus)FR
 cypress oilFR
 dihydro-alpha-iononeFL/FR
 dihydro-beta-iononeFL/FR
 dihydrorose oxideFR
 dimethyl benzyl carbinyl butyrateFL/FR
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetateFL/FR
 estragoleFL/FR
 ethyl 4-pentenoateFL/FR
dextro-fenchoneFL/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
(E,E)-2,4-hexadien-1-olFL/FR
(E)-4-hexen-1-ol 
(Z)-4-hexen-1-olFL/FR
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
para-menthane-3,8-diolFL/FR
(E)-6-methyl-3-hepten-2-oneFL/FR
 niaouli oilFR
 nonisyl formateFR
 oakmoss absoluteFL/FR
(E)-2-octenalFL/FR
1-octen-3-yl acetateFL/FR
 origanum oil greeceFL/FR
 origanum oilFL/FR
 orris hexanoneFR
2-pentyl cyclopentanoneFR
 perillaldehydeFL/FR
 petitgrain combava oilFR
 pinacolFR
 pine hexanolFR
alpha-pineneFL/FR
2-propyl thiazoleFL
(-)-isopulegolFL/FR
 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
beta-terpineolFL/FR
alpha-thujene 
 verdoxanFR
 tropical indeneFR
 turmeric oleoresinFL
 vetiver oil haitiFL/FR
 viridiflorolFL/FR
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Potential Uses:
 blueberryFR
 citrusFR
 earth humusFR
 herbalFR
 limeFR
 spiceFR
 strawberryFR
 woodyFR
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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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Synonyms:
 bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)-
2-norbornanol, 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
1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
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Articles:
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:
 alcohol
 water, 461.4 mg/L @ 25 °C (est)
Insoluble in:
 water
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