EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(-)-alpha-fenchol
L-alpha-fenchyl alcohol

Sponsors

Name:(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
CAS Number: 512-13-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-135-9
FDA UNII:UJ108AQX3M
Nikkaji Web:J156.725J
Beilstein Number:2038083
XlogP3-AA:2.50 (est)
Molecular Weight:154.25266000
Formula:C10 H18 O
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
 
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)
Soluble in:
 alcohol
 water, 461.4 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Type: earthy
Odor Strength:medium
Substantivity:12 hour(s) at 100.00 %
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)
Flavor Type: camphoreous
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)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
(1S,2S,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol
Parchem
(-)-alpha-Fenchol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
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
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
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
 
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
 
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
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
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
amber
sports
amber fragrance
FR
anisic
estragole
FL/FR
balsamic
dextro-
borneol
FL/FR
laevo-
borneol
FL/FR
dextro,laevo-
borneol
FL/FR
iso
bornyl formate
FL/FR
iso
bornyl methyl ether
FL/FR
iso
bornyl propionate
FL/FR
cinnamyl formate
FL/FR
dextro-
fenchone
FL/FR
fir needle oil siberia
FL/FR
hexyl benzoate
FL/FR
camphoreous
2,6-
dimethyl-3-oxatricyclo(4.2.1.0*2,4*)nonane
FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
hinoki leaf oil
FR
melaleuca viridiflora leaf oil
CS
citrus
(E+Z)-4,8-
dimethyl-3,7-nonadien-2-yl acetate
FL/FR
petitgrain combava oil
FR
clean
cyclododecyl formate
FR
ethereal
ethyl 4-pentenoate
FL/FR
fatty
(E)-2-
octenal
FL/FR
floral
bois de rose oil peru
FL/FR
dihydro-alpha-ionone
FL/FR
dihydrorose oxide
FR
dimethyl benzyl carbinyl butyrate
FL/FR
geranium oil africa
FL/FR
geranium oil egypt
FL/FR
ho leaf oil
FR
lavender oil
FL/FR
linalool oxide
FL/FR
2-
pentyl cyclopentanone
FR
rose pyran
FR
fruity
3-
allyl oxy-1,4-dimethyl bicyclo(3.2.1)octane
FR
tropical indene
FR
green
iso
butyl heptanoate
FL/FR
iso
butyl methyl ketone
FL/FR
2-sec-
butyl thiazole
FL/FR
iso
cyclocitral (IFF)
FL/FR
galbanum oil
FL/FR
heptanal (aldehyde C-7)
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
3-
hexenyl 2-methyl butyrate
FL/FR
english
ivy leaf absolute
FR
seaweed absolute (fucus vesiculosus et serratus)
FL/FR
herbal
1-
allyl-2,2,7,7-tetramethyl cycloheptanol
FR
1,8-
cineole
FL/FR
1,4-
cineole
FL/FR
ortho-
cresyl salicylate
FL/FR
dimethyl cyclormol (IFF)
FR
geranic oxide
FL/FR
cis-
herbal cyclohexane
FR
herbal dioxane
FR
herbal undecane
FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
hyssop oil
FL/FR
spike
lavender oil
FL/FR
spike
lavender oil spain
FL/FR
linalyl formate
FL/FR
melaleuca leucadendron cajaputi oil
FL/FR
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
melaleuca linariifolia oil
FR
melaleuca quinquenervia water
FR
para-
menthane-3,8-diol
FL/FR
methyl cyclogeranate (Firmenich)
FR
(E)-6-
methyl-3-hepten-2-one
FL/FR
niaouli oil
FR
nonisyl formate
FR
1-
octen-3-yl acetate
FL/FR
origanum oil
FL/FR
origanum oil greece
FL/FR
perillaldehyde
FL/FR
pine hexanol
FR
alpha-
pinene
FL/FR
rosemary absolute
FL/FR
rosemary oil
FL/FR
rosemary oil africa
FL/FR
rosemary oil morocco
FL/FR
rosemary oil spain
FL/FR
rosemary oil tunisia
FL/FR
rosemary specialty
FR
sabinene hydrate
FL/FR
tagete oil CO2 extract
FL/FR
tagete oil rwanda
FL/FR
tagete oil south africa
FL/FR
terpineols (unspec.) (mixed isomers)
FL/FR
viridiflorol
FL/FR
mentholic
laevo-
menthol
FL/FR
peppermint cyclohexanone
FL/FR
minty
(-)-iso
pulegol
FL/FR
mossy
oakmoss absolute
FL/FR
musk
acetyl ethyl tetramethyl tetralin replacer
FR
naphthyl
para-
methyl anisole
FL/FR
spicy
4-
carvomenthenol
FL/FR
cuminaldehyde
FL/FR
elettaria cardamomum seed oil
FL/FR
marjoram oil (thymus mastichina) spain
FL/FR
white
sassafras oil
FL/FR
terpenic
cypress leaf oil
FR
thujonic
cedarleaf oil terpeneless
FR
sage oil (salvia lavandulifolia vahl.) spain
FL/FR
sage oil dalmatian
FL/FR
woody
iso
bornyl isovalerate
FL/FR
2-tert-
butyl cyclohexanone
FR
camphene
FL/FR
epoxidized
cedarwood oil
FR
cyperus root oil (cyperus scariosus)
FR
dihydro-beta-ionone
FL/FR
herbal norbornane
FR
hinoki root oil
FR
indisan (IFF)
FR
juniper berry oil terpenes
FR
orris hexanone
FR
pinacol
FR
sandal cyclohexanol
FR
sandela
FR
santall
FR
beta-
terpineol
FL/FR
verdoxan
FR
vetiver oil haiti
FL/FR
woody octene
FR
zedoary bark oil
FL/FR
For Flavor
No flavor group found for these
dextro-
borneol
FL/FR
dextro,laevo-
borneol
FL/FR
iso
bornyl methyl ether
FL/FR
iso
butyl heptanoate
FL/FR
4-
butyl thiazole
FL
2-sec-
butyl thiazole
FL/FR
ortho-
cresyl salicylate
FL/FR
(E+Z)-4,8-
dimethyl-3,7-nonadien-2-yl acetate
FL/FR
ethyl 4-pentenoate
FL/FR
fig leaf absolute
FL
(E,E)-2,4-
hexadien-1-ol
FL
linalyl formate
FL/FR
melaleuca leucadendron cajaputi oil
FL/FR
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
para-
menthane-3,8-diol
FL/FR
(E)-6-
methyl-3-hepten-2-one
FL/FR
2-
propyl thiazole
FL
white
sassafras oil
FL/FR
seaweed absolute (fucus vesiculosus et serratus)
FL/FR
beta-
terpineol
FL/FR
terpineols (unspec.) (mixed isomers)
FL/FR
viridiflorol
FL/FR
balsamic
balsamic
iso
bornyl propionate
FL/FR
fir needle oil siberia
FL/FR
berry
dihydro-alpha-ionone
FL/FR
camphoreous
laevo-
borneol
FL/FR
camphene
FL/FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
geranic oxide
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
rosemary oil tunisia
FL/FR
cooling
4-
carvomenthenol
FL/FR
1,4-
cineole
FL/FR
dextro-
fenchone
FL/FR
spike
lavender oil
FL/FR
iso
menthol
FL
laevo-
menthol
FL/FR
sabinene hydrate
FL/FR
fatty
(E)-2-
octenal
FL/FR
floral
bois de rose oil peru
FL/FR
dimethyl benzyl carbinyl butyrate
FL/FR
geranium oil africa
FL/FR
geranium oil egypt
FL/FR
fruity
tagete oil CO2 extract
FL/FR
tagete oil rwanda
FL/FR
tagete oil south africa
FL/FR
green
iso
butyl methyl ketone
FL/FR
iso
cyclocitral (IFF)
FL/FR
galbanum oil
FL/FR
heptanal (aldehyde C-7)
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
3-
hexenyl 2-methyl butyrate
FL/FR
hexyl benzoate
FL/FR
linalool oxide
FL/FR
oakmoss absolute
FL/FR
1-
octen-3-yl acetate
FL/FR
herbal
2-
acetoxy-1,8-cineole
FL
hyssop oil
FL/FR
lavender oil
FL/FR
spike
lavender oil spain
FL/FR
origanum oil
FL/FR
origanum oil greece
FL/FR
rosemary absolute
FL/FR
rosemary oil
FL/FR
rosemary oil africa
FL/FR
rosemary oil morocco
FL/FR
rosemary oil spain
FL/FR
sage oil (salvia lavandulifolia vahl.) spain
FL/FR
licorice
estragole
FL/FR
mentholic
peppermint cyclohexanone
FL/FR
minty
1,8-
cineole
FL/FR
(-)-iso
pulegol
FL/FR
naphthyl
para-
methyl anisole
FL/FR
spicy
cinnamyl formate
FL/FR
cuminaldehyde
FL/FR
elettaria cardamomum seed oil
FL/FR
marjoram oil (thymus mastichina) spain
FL/FR
perillaldehyde
FL/FR
turmeric oleoresin
FL
thujonic
sage oil dalmatian
FL/FR
woody
iso
bornyl formate
FL/FR
iso
bornyl isovalerate
FL/FR
dihydro-beta-ionone
FL/FR
alpha-
pinene
FL/FR
vetiver oil haiti
FL/FR
zedoary bark oil
FL/FR
 
Potential Uses:
FRblueberry
FRcitrus
FRearth
FRherbal
FRlime
FRspice
FRstrawberry
FRwoody
 
Occurrence (nature, food, other):note
 basil shoot oil
Search Trop Picture
 bergamot oil @ 0.01%
Data GC Search Trop Picture
 boldo leaf oil italy @ 0.40%
Data GC Search Trop Picture
 boldus leaf oil chile @ 0.22%
Data GC Search Trop Picture
 carrot weed oil @ 0.76%
Data GC Search Trop Picture
 cascarilla bark oil @ 0.01%
Data GC Search Trop Picture
 cypress cone oil egypt @ 0.2%
Data GC Search Trop Picture
 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 0.20%
Data GC Search Trop Picture
 eucalyptus dalrympleana maiden leaf oil ethiopia @ 3.10%
Data GC Search Trop Picture
 eucalyptus delegatensis r. baker leaf oil ethiopia @ 0.80%
Data GC Search Trop Picture
 eucalyptus globulus maidenii f. muell oil @ 0.07%
Data GC Search Trop Picture
 eucalyptus globulus pseudoglobulus oil @ 0.10%
Data GC Search Trop Picture
 eucalyptus grandis w. hill ex maiden leaf oil ethiopia @ 0.60%
Data GC Search Trop Picture
 eucalyptus urophylla s.t. blake leaf oil ethiopia @ 0.70%
Data GC Search Trop Picture
 hinoki leaf oil @ 2.09%
Data GC Search Trop Picture
 hinoki root oil @ 0.71%
Data GC Search Trop Picture
 hinoki wood oil @ 0.42%
Data GC Search Trop Picture
 hypericum dogonbadanicum assadi oil iran @ 0.70%
Data GC Search Trop Picture
 lemongrass oil morocco @ 0.10%
Data GC Search Trop Picture
 lime oil distilled mexico @ 0.79%
Data GC Search Trop Picture
 lime oil distilled peru @ 0.82%
Data GC Search Trop Picture
 lovage root
Search Trop Picture
 marjoram oil sweet morocco @ 1.68%
Data GC Search Trop Picture
 mastic fruit oil @ 0.58%
Data GC Search Trop Picture
 mastic leaf oil @ 0.14%
Data GC Search Trop Picture
 pine needle oil scotch siberia @ 0.1-0.2%
Data GC Search Trop Picture
 plectranthus glandulosus hook f. leaf oil cameroon @ 1.50%
Data GC Search Trop Picture
 pteronia oil @ 0.10%
Data GC Search Trop Picture
 rosemary leaf oil
Search Trop Picture
 rosemary plant
Search Trop Picture
 thyme oil wild or creeping pakistan @ 0.91%
Data GC Search Trop Picture
 
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
 

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.
 
Notes:
None found
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