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

isopulegol
p-menth-8-en-3-ol

Sponsors

Name:5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
CAS Number: 7786-67-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:232-102-8
Nikkaji Web:J36.816D
XlogP3-AA:3.00 (est)
Molecular Weight:154.25266000
Formula:C10 H18 O
BioActivity Summary:listing
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
PubMed:Search
NCBI:Search
FEMA Number:2962 isopulegol
FDA Mainterm: ISOPULEGOL
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 197.00 to 198.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.099000 mm/Hg @ 25.00 °C. (est)
Flash Point: 173.00 °F. TCC ( 78.30 °C. ) (est)
logP (o/w): 2.724 (est)
Soluble in:
 alcohol
 water, 308.6 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
Substantivity:28 hour(s) at 100.00 %
minty cooling medicinal woody green grassy herbal
Odor Description:at 10.00 % in dipropylene glycol. minty cooling medicinal woody green grassy herbal
Luebke, William tgsc, (1985)
minty cooling medicinal woody green herbal
Odor Description:Minty, cooling, medicinal, woody with a green herbaceous undernote
Mosciano, Gerard P&F 15, No. 6, 35, (1990)
Flavor Type: minty
minty cooling herbal peppermint
Taste Description: at 30.00 ppm. Minty cooling, herbaceous peppermint nuance
Mosciano, Gerard P&F 15, No. 6, 35, (1990)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: masking agents
 
Suppliers:
Berjé
isoPulegol
Happening at Berje
BOC Sciences
For experimental / research use only.
p-Menth-8-en-3-ol
Citrus and Allied Essences
isoPulegol Extra FCC
Market Report
Coompo
For experimental / research use only.
isoPulegol from Plants ≥98%
Odor: characteristic
Use: Isopulegol is a monoterpene alcohol intermediate in the preparation of (-)-menthol and it is present in the essential oils of various plants. This work presents behavioral effects of isopulegol in animal models of open field, elevated plus maze (EPM), rota rod, hole board, barbiturate-induced sleeping time, tail suspension and forced swimming tests in mice. Isopulegol was administered intraperitoneally to male mice at single doses of 25 and 50 mg/kg, while diazepam 1 or 2 mg/kg and imipramine 10 or 30 mg/kg were used as standard drugs. The results showed that, similar to diazepam (1 mg/kg), both doses of isopulegol significantly modified all the observed parameters in the EPM test, without alter the general motor activity in the open field test. In the same way, both doses of isopulegol increased the number of head dips in the hole-board test. Forced swimming and tail suspension tests showed that isopulegol (25 and 50 mg/kg) was able to induce a significant increase in the immobility time, in opposite to imipramine, a recognized antidepressant drug. There was a decrease in the sleep latency time and prolongation of the pentobarbital-induced sleeping time with both doses of Isopulegol. Different from diazepam (2 mg/kg), isopulegol (25 e 50 mg/kg) had no effect on the motor coordination of animals in the rota rod test. These results showed that isopulegol presented depressant- and anxiolytic-like effects. The anticonvulsant and bioprotective effects of isopulegol against PTZ-induced convulsions are possibly related to positive modulation of benzodiazepine-sensitive GABAA receptors and to antioxidant properties.
Diffusions Aromatiques
isoPULEGOL
Global Essence
isoPulegol
Moellhausen
isoPULEGOL
PCAS
isoPulegol, Kosher
Penta International
L-isoPULEGOL, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
isoPulegol
TCI AMERICA
For experimental / research use only.
isoPulegol >90.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
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 37/39 - Wear suitable gloves and eye/face protection.
 
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:
oral-rat LD50 1030 ul/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 823, 1975.

Dermal Toxicity:
skin-rabbit LD50 3 ml/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 823, 1975.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
maximum skin levels for fine fragrances:
  0.0500 % 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 isopulegol usage levels up to:
  6.0000 % in the fragrance concentrate.
Dermal Systemic Exposure in Cosmetic Products:
 0.0007 mg/kg/day (IFRA, 2004)
 
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. Update in publication number(s): 22
 average usual ppmaverage maximum ppm
baked goods: 14.0000019.00000
beverages(nonalcoholic): 50.00000200.00000
beverages(alcoholic): 50.00000200.00000
breakfast cereal: --
cheese: --
chewing gum: 500.000001000.00000
condiments / relishes: --
confectionery froastings: 100.00000500.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 12.0000015.00000
fruit ices: --
gelatins / puddings: 50.00000200.00000
granulated sugar: --
gravies: --
hard candy: 100.00000500.00000
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: 100.00000500.00000
soups: --
sugar substitutes: --
sweet sauces: --
 
Safety References:
EPI System: View
EPA Substance Registry Services (TSCA):7786-67-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :24585
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
Chemidplus:0007786676
RTECS:OT0190000 for cas# 7786-67-6
 
References:
 5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:7786-67-6
Pubchem (cid):24585
Pubchem (sid):135019731
Pherobase:View
 
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
FDA Everything Added to Food in the United States (EAFUS):View
HMDB (The Human Metabolome Database):HMDB36077
FooDB:FDB014911
Export Tariff Code:2905.22.5050
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
alliaceous
dibutyl sulfide
FL/FR
balsamic
betula pubescens bud oil
FL/FR
fir balsam absolute
FR
fir balsam concrete
FR
citrus
bergamot acetoacetate
FR
lemongrass oil
FL/FR
lime oil fractions
FR
litsea cubeba fruit oil
FL/FR
alpha-
methylene citronellal
FR
neroli ketone
FR
floral
dihydrocarvyl acetate
FL/FR
glycoacetal
FR
karo karounde absolute
FR
linalool
FL/FR
melaleuca ericifolia leaf oil
FR
mimosa absolute
FL/FR
mimosa absolute france
FL/FR
mimosa absolute india
FL/FR
mimosa absolute morocco
FL/FR
orange leaf absolute
FL/FR
fruity
cyclohexyl crotonate
FR
1,4-
dibutyl-6,8-dioxabicyclo(3.2.1)octane
FR
1,4-
diisopropyl-6,8-dioxabicyclo(3.2.1)octane
FR
grapefruit acetal
FR
(Z)-3-
hexen-1-yl isobutyrate
FL/FR
2-
methyl-2-pentenal
FL/FR
prenyl ethyl ether
FL/FR
green
alfalfa absolute
FR
alfalfa oil
FL/FR
alfalfa resinoid
FL/FR
bark carbaldehyde
FR
bergoxane
FR
butyl 2-methyl butyrate
FL/FR
butyl heptanoate
FL/FR
sec-
butyl-3-methyl but-2-ene thioate
FL/FR
citral / diisotridecyl acetal
FR
3,7-
dimethyl-6-octenoic acid
FL/FR
fresh nitrile
FR
galbanum oleoresin
FL/FR
galbanum resinoid
FL/FR
green specialty
FR
(Z)-3-
hepten-1-ol
FL/FR
3-
hepten-2-one
FL/FR
(Z)-3-
hexen-1-ol
FL/FR
hexyl butyrate
FL/FR
hexyl hexanoate
FL/FR
thiogeraniol
FL/FR
3,5,5-
trimethyl hexanol
FL/FR
herbal
buchu oxime
FR
(+)-alpha-
campholenic aldehyde
FL/FR
canarium luzonicum oil
FL/FR
1,8-
cineole
FL/FR
1,4-
cineole
FL/FR
clary sage resin america
FR
iso
dihydrolavandulal
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
myrtenol
FL/FR
nonisyl formate
FR
oregano specialty
FR
piperitone
FL/FR
sabinene hydrate
FL/FR
theaspirane
FL/FR
tricyclo(5.2.1.02,6)dec-3-enyl acetate
FR
medicinal
meta-
dimethyl hydroquinone
FL/FR
mentholic
cornmint oil china
FL/FR
cornmint oil terpeneless
FL/FR
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
(±)-iso
menthone
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
dextro-
dihydrocarvone
FL/FR
diosphenol
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
laevo-
menthyl lactate
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil fractions
FL/FR
peppermint absolute
FL/FR
peppermint oil america
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
iso
propyl tiglate
FL/FR
(-)-iso
pulegol
FL/FR
iso
pulegone
FL/FR
(R)-(+)-
pulegone
FL/FR
2,4,4,6-
tetramethyl cyclohexa-2,5-diene-1-one
FR
phenolic
4-
methyl-2,6-dimethoxyphenol
FL/FR
pine
pine oil 85
FR
spicy
clove bud oil
FL/FR
2,5-
dimethyl bicyclo(3.2.1)-2-octen-3-yl acetate + 1,4-dimethyl bicyclo(3.2.1)-2-octen-3-yl acetate
FR
2-
octanol
FL/FR
black
pepper oil CO2 extract
FL/FR
sulfurous
buchu mercaptan
FL/FR
mango thiol
FL/FR
passiflora acetate
FL/FR
terpenic
juniper branch oil
FR
alpha-
phellandrene
FL/FR
woody
bruyere root absolute
FR
(+)-
camphene
FL/FR
camphene
FL/FR
alpha-
farnesene
FL/FR
alpha-
farnesene isomer
FL/FR
humulus lupulus extract
FL/FR
longifolene
FL/FR
moss naphthaleneol
FR
(±)-
tetrahydronootkatone
FL/FR
xanthoxylum alatum roxb. oil
FR
For Flavor
No flavor group found for these
2-
acetyl-4-isopropenyl pyridine
FL
2-
acetyl-4-isopropyl pyridine
FL
betula pubescens bud oil
FL/FR
butyl 2-methyl butyrate
FL/FR
sec-
butyl-3-methyl but-2-ene thioate
FL/FR
(+)-
camphene
FL/FR
diosphenol
FL/FR
3-(2-
furyl) acrolein
FL
(Z)-3-
hepten-1-ol
FL/FR
2-
heptenoic acid
FL
(Z)-3-
hexenoic acid
FL
menthyl acetate racemic
FL/FR
3-(
methyl thio) hexanal
FL
(E,E)-3,5-
octadien-2-one
FL
prenyl ethyl ether
FL/FR
iso
pulegone
FL/FR
(±)-
tetrahydronootkatone
FL/FR
2,4,4-
trimethyl-1,3-oxathiane
FL
camphoreous
camphoreous
camphene
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
chemical
meta-
dimethyl hydroquinone
FL/FR
citrus
lemongrass oil
FL/FR
linalool
FL/FR
litsea cubeba fruit oil
FL/FR
cooling
1,4-
cineole
FL/FR
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
laevo-
menthyl lactate
FL/FR
peppermint oil america
FL/FR
sabinene hydrate
FL/FR
theaspirane
FL/FR
WS-3
FL
creamy
3-
hepten-2-one
FL/FR
floral
dihydrocarvyl acetate
FL/FR
3,7-
dimethyl-6-octenoic acid
FL/FR
mimosa absolute morocco
FL/FR
orange leaf absolute
FL/FR
fruity
butyl heptanoate
FL/FR
(Z)-3-
hexen-1-yl isobutyrate
FL/FR
hexyl hexanoate
FL/FR
2-
methyl-2-pentenal
FL/FR
green
alfalfa oil
FL/FR
alfalfa resinoid
FL/FR
(+)-alpha-
campholenic aldehyde
FL/FR
canarium luzonicum oil
FL/FR
dibutyl sulfide
FL/FR
dextro-
dihydrocarvone
FL/FR
alpha-
farnesene
FL/FR
alpha-
farnesene isomer
FL/FR
galbanum oleoresin
FL/FR
galbanum resinoid
FL/FR
(Z)-3-
hexen-1-ol
FL/FR
hexyl butyrate
FL/FR
iso
propyl tiglate
FL/FR
3,5,5-
trimethyl hexanol
FL/FR
herbal
iso
dihydrolavandulal
FL/FR
mentholic
cornmint oil terpeneless
FL/FR
peppermint cyclohexanone
FL/FR
minty
1,8-
cineole
FL/FR
cornmint oil china
FL/FR
homo
menthol
FL/FR
(±)-iso
menthone
FL/FR
(-)-
menthone
FL/FR
myrtenol
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil fractions
FL/FR
peppermint absolute
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
piperitone
FL/FR
dextro-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
(R)-(+)-
pulegone
FL/FR
thiogeraniol
FL/FR
orris
costus root oil
FL
phenolic
4-
methyl-2,6-dimethoxyphenol
FL/FR
spicy
clove bud oil
FL/FR
2-
octanol
FL/FR
black
pepper oil CO2 extract
FL/FR
sulfurous
buchu mercaptan
FL/FR
mango thiol
FL/FR
terpenic
alpha-
phellandrene
FL/FR
tropical
passiflora acetate
FL/FR
vegetable
potato butyraldehyde
FL
waxy
mimosa absolute
FL/FR
mimosa absolute france
FL/FR
mimosa absolute india
FL/FR
woody
humulus lupulus extract
FL/FR
longifolene
FL/FR
iso
pulegyl acetate
FL/FR
 
Potential Uses:
 apricotFR
 caramelFL
 cherryFR
 citronellaFL/FR
 eucalyptusFL/FR
 geraniumFR
 herbalFR
 lemongrassFR
 mandarinFR
 mintFR
 oral care agents 
 peachFR
 pennyroyalFL/FR
 peppermintFR
 plumFR
 raspberryFR
 rose leafFL/FR
 spearmintFR
 tuberoseFR
 
Occurrence (nature, food, other):note
 angelica seed oil CO2 extract @ 1.40%
Data GC Search Trop Picture
 bergamot oil @ 0.000-0.004%
Data GC Search Trop Picture
 cascarilla bark oil @ 0.05%
Data GC Search Trop Picture
 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 3.80%
Data GC Search Trop Picture
 eucalyptus citriadora
Search Trop Picture
 eucalyptus citriodora oil @ 3.41%
Data GC Search Trop Picture
 eucalyptus globulus oil pakistan @ 0.20%
Data GC Search Trop Picture
 geranium
Search Trop Picture
 grapefruit oil c.p. @ 0.05%
Data GC Search Trop Picture
 grapefruit oil c.p. @ 0.06%
Data GC Search Trop Picture
 grapefruit oil c.p. italy @ 0.04%
Data GC Search Trop Picture
 laurel leaf oil turkey @ 0.10%
Data GC Search Trop Picture
 lemon verbena oil morocco @ 0.7%
Data GC Search Trop Picture
 lemongrass
Search Trop Picture
 lemongrass oil @ 0.26%
Data GC Search Trop Picture
 lemongrass oil @ 1.23%
Data GC Search Trop Picture
 lemongrass oil morocco @ 0.30%
Data GC Search Trop Picture
 lime oil distilled peru @ 0.08%
Data GC Search Trop Picture
 mandarin
Search Trop Picture
 mandarin oil @ trace%
Data GC Search Trop Picture
 mandarin oil italy @ trace%
Data GC Search Trop Picture
 mint
Search Trop Picture
 pennyroyal oil @ trace%
Data GC Search Trop Picture
 petitgrain combava oil @ 0.32%
Data GC Search Picture
 petitgrain grapefruit oil @ 0.60%
Data GC Search Trop Picture
 petitgrain lime oil @ 0.10%
Data GC Search Trop Picture
 petitgrain sweet oil @ 0.51%
Data GC Search Picture
 pseudotsuga menziesii
Search Trop Picture
 pteronia oil @ 0.10%
Data GC Search Trop Picture
 rum
Search PMC Picture
 sage oil england @ 0.10%
Data GC Search Trop Picture
 wormseed oil spain @ 3.54%
Data GC Search Trop Picture
 
Synonyms:
p-menth-8-en-3-ol
para-menth-8-en-3-ol
8(9)-p-menthen-3-ol
8(9)-para-menthen-3-ol
5-methyl-2-(1-methyl vinyl) cyclohexan-1-ol
5-methyl-2-(1-methylvinyl)cyclohexan-1-ol
5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
1-methyl-4-isopropenyl cyclohexan-3-ol
isopulegol extra FCC
 

Articles:

PubMed:Intramolecular Hydrogen Transfer Reaction: Menthon from Isopulegol.
PubMed:Airborne Antituberculosis Activity of Eucalyptus citriodora Essential Oil.
PubMed:Saturated Long-Chain Esters of Isopulegol as Novel Permeation Enhancers for Transdermal Drug Delivery.
PubMed:In Vivo Potential Anti-Inflammatory Activity of Melissa officinalis L. Essential Oil.
PubMed:GABA(A) receptor modulation by terpenoids from Sideritis extracts.
PubMed:β-Cyclodextrin as the suitable molecular container for isopulegol enantiomers.
PubMed:Effect of unsaturated menthol analogues on the in vitro penetration of 5-fluorouracil through rat skin.
PubMed:Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans.
PubMed:Olfactory discrimination ability of South African fur seals (Arctocephalus pusillus) for enantiomers.
PubMed:Revision of the stereochemistry of elisabethatriene, a putative biosynthetic intermediate of pseudopterosins.
PubMed:Prokaryotic squalene-hopene cyclases can be converted to citronellal cyclases by single amino acid exchange.
PubMed:MOFs as multifunctional catalysts: one-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst.
PubMed:Activation-independent cyclization of monoterpenoids.
PubMed:A DFT analysis of thermal decomposition reactions important to natural products.
PubMed:Bioactivity against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) of Cymbopogon citratus and Eucalyptus citriodora essential oils grown in Colombia.
PubMed:Characterization and antioxidant activity of essential oils from fresh and decaying leaves of Eucalyptus tereticornis.
PubMed:Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.
PubMed:Effects of isopulegol on pentylenetetrazol-induced convulsions in mice: possible involvement of GABAergic system and antioxidant activity.
PubMed:Gastroprotective activity of isopulegol on experimentally induced gastric lesions in mice: investigation of possible mechanisms of action.
PubMed:Reactivity in the confined spaces of zeolites: the interplay between spectroscopy and theory to develop structure-activity relationships for catalysis.
PubMed:Cyclisation of citronellal over heterogeneous inorganic fluorides--highly chemo- and diastereoselective catalysts for (+/-)-isopulegol.
PubMed:Zr-zeolite beta: a new heterogeneous catalyst system for the highly selective cascade transformation of citral to (+/-)-menthol.
PubMed:A cavitand with a fluorous rim acts as an amine receptor.
PubMed:Synthesis of a dialuminum-substituted silicotungstate and the diastereoselective cyclization of citronellal derivatives.
PubMed:Fragrance Material Review on isopulegol.
PubMed:Menthol shares general anesthetic activity and sites of action on the GABA(A) receptor with the intravenous agent, propofol.
PubMed:Sedative effect of monoterpene alcohols in mice: a preliminary screening.
PubMed:Central nervous system activity of acute administration of isopulegol in mice.
PubMed:Synthesis of +-dihydro-epi-deoxyarteannuin B.
PubMed:Probing the Lewis acidity and catalytic activity of the metal-organic framework [Cu3(btc)2] (BTC=benzene-1,3,5-tricarboxylate).
PubMed:Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
PubMed:The essential oils from Zanthoxylum schinifolium pericarp induce apoptosis of HepG2 human hepatoma cells through increased production of reactive oxygen species.
PubMed:The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.
PubMed:The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel.
PubMed:Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
PubMed:Sn-Beta zeolite as diastereoselective water-resistant heterogeneous Lewis-acid catalyst for carbon-carbon bond formation in the intramolecular carbonyl-ene reaction.
PubMed:Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations.
PubMed:About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes.
PubMed:Changes in essential oil during enzyme-assisted ensiling of lemongrass (Cymbopogon citratus Stapf.) and lemon eucalyptus (Eucalyptus citriodora Hook).
PubMed:A short route to (-)-mintlactone by thallium(III)-mediated cyclization of (-)-isopulegol.
PubMed:Ethnobotany, volatile oils and secretion tissues of werneria poposa from Argentina.
PubMed:Comparison of antimicrobial properties of monoterpenes and their carbonylated products.
PubMed:Pheromone syntheses: a tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate.
 
Notes:
Various stereoisomers occur in essential oils. Flavouring agent
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