Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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 mmHg @ 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). |
|
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Cosmetic Information:
Suppliers:
Berjé |
isoPulegol
|
Media |
BOC Sciences |
For experimental / research use only. |
p-Menth-8-en-3-ol
|
Citrus and Allied Essences |
isoPulegol Extra FCC
|
Market Report |
CJ Latta & Associates |
ISOPULEGOL
|
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
|
Penta International |
L-ISOPULEGOL
|
Santa Cruz Biotechnology |
For experimental / research use only. |
isoPulegol
|
Seqens |
isoPulegol, Kosher
|
Som Extracts |
ISO PULEGOL
|
Synerzine |
ISOPULEGOL, SUM OF ISOMERS
|
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 |
RIFM Fragrance Material Safety Assessment: Search |
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
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 |
Click here to view publication 3 |
| average usual ppm | average maximum ppm |
baked goods: | 14.00000 | 19.00000 |
beverages(nonalcoholic): | 50.00000 | 200.00000 |
beverages(alcoholic): | 50.00000 | 200.00000 |
breakfast cereal: | - | - |
cheese: | - | - |
chewing gum: | 500.00000 | 1000.00000 |
condiments / relishes: | - | - |
confectionery froastings: | 100.00000 | 500.00000 |
egg products: | - | - |
fats / oils: | - | - |
fish products: | - | - |
frozen dairy: | 12.00000 | 15.00000 |
fruit ices: | - | - |
gelatins / puddings: | 50.00000 | 200.00000 |
granulated sugar: | - | - |
gravies: | - | - |
hard candy: | 100.00000 | 500.00000 |
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: | 100.00000 | 500.00000 |
soups: | - | - |
sugar substitutes: | - | - |
sweet sauces: | - | - |
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 |
AIDS Citations: | Search |
Cancer Citations: | Search |
Toxicology Citations: | Search |
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:
Other Information:
Potential Blenders and core components note
|
For Odor |
No odor group found for these |
(-)-gamma- | elemene | |
alliaceous |
| dibutyl sulfide | FL/FR |
balsamic |
| betula pubescens bud oil | FL/FR |
| fir balsam absolute | FR |
| fir balsam absolute replacer | FL/FR |
| fir balsam concrete | FR |
camphoreous |
| camphor tree bark oil | FL/FR |
| eucalyptus polybractea oil | FR |
citrus |
| bergamot acetoacetate | FR |
| elemi oil replacer | FR |
| lemon balm fragrance | FR |
| lemongrass fragrance | FR |
| lemongrass oil | FL/FR |
| lemongrass oil replacer | FR |
| lime oil fractions | FR |
| litsea cubeba fruit oil | FL/FR |
| melissa oil replacer | FR |
alpha- | methylene citronellal | FR |
| neroli ketone | FR |
dry |
| autumn specialty | FR |
floral |
| coriander seed oil terpeneless | FL/FR |
| dihydrocarvyl acetate | FL/FR |
| glycoacetal | FR |
| karo karounde absolute | FR |
| karo karounde absolute replacer | 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 |
| mimosa absolute replacer | FR |
| mimosa fragrance | FR |
| mimosa specialty | FR |
| orange leaf absolute | FL/FR |
| orris rhizome absolute (iris germanica) | FL/FR |
fruity |
| butyl 2-methyl butyrate | FL/FR |
| 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 |
1,2- | dimethyl propyl 2-butenoate | |
| grapefruit acetal | FR |
(Z)-3- | hexen-1-yl isobutyrate | FL/FR |
2- | methyl-2-pentenal | FL/FR |
| prenyl ethyl ether | FL/FR |
| alfalfa absolute | FR |
| alfalfa oil | FL/FR |
| alfalfa resinoid | FL/FR |
| bark carbaldehyde | FR |
| bergoxane | FR |
| bicyclogermacrene | |
| 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 |
| elemi specialty | FR |
alpha- | elemol | FL/FR |
| forest fragrance | FR |
| fresh nitrile | FR |
| galbanum oleoresin | FL/FR |
| galbanum resinoid | FL/FR |
| galbanum resinoid replacer | FR |
| green fragrance | FR |
| green specialty | FR |
(Z)-3- | hepten-1-ol | FL/FR |
3- | hepten-2-one | FL/FR |
(Z)-3- | hexen-1-ol | FL/FR |
(Z)-3- | hexen-1-yl (E)-2-hexenoate | FL/FR |
| hexyl butyrate | FL/FR |
| hexyl hexanoate | FL/FR |
| thiogeraniol | FL/FR |
| tricyclene-9-butenone | |
3,5,5- | trimethyl hexanol | FL/FR |
2,2,4- | trimethyl-1,3-oxathiane | |
herbal |
| buchu oxime | FR |
(+)-alpha- | campholenic aldehyde | FL/FR |
| camphor wood oil decamphorised | 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 |
| laurus nobilis leaf oil | 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 |
leafy |
| autumn fragrance | FR |
medicinal |
meta- | dimethyl hydroquinone | FL/FR |
mentholic |
| cornmint oil | FL/FR |
| cornmint oil china | FL/FR |
| cornmint oil terpeneless | FL/FR |
laevo- | menthol | FL/FR |
dextro,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 |
homo | menthyl acetate | FL/FR |
laevo- | menthyl lactate | FL/FR |
| mint fragrance | FR |
| mint specialty | FR |
| pennyroyal oil | FL/FR |
| pennyroyal oil fractions | FL/FR |
| peppermint absolute | FL/FR |
| peppermint distillates | FL/FR |
| peppermint fragrance | FR |
| peppermint oil america | FL/FR |
| peppermint oil idaho | FL/FR |
| peppermint oil special fractions | FL/FR |
| peppermint oil terpeneless | FL/FR |
| peppermint oil willamette | FL/FR |
laevo- | piperitone | FL/FR |
iso | propyl tiglate | FL/FR |
(-)-iso | pulegol | FL/FR |
iso | pulegone | FL/FR |
(R)-(+)- | pulegone | 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 |
3-(2- | furyl) acrolein | FL/FR |
| laurel leaf oil replacer | FR |
2- | octanol | FL/FR |
black | pepper oil CO2 extract | FL/FR |
| tea tree oil | 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 |
| costus specialty | FR |
alpha- | farnesene | FL/FR |
alpha- | farnesene isomer | FL/FR |
| furfuryl thenyl ether | |
| humulus lupulus extract | FL/FR |
| juniper fragrance | FR |
| longifolene | FL/FR |
| moss naphthaleneol | FR |
(±)- | tetrahydronootkatone | FL/FR |
alpha- | thujene | |
| 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 |
| bicyclogermacrene | |
sec- | butyl-3-methyl but-2-ene thioate | FL/FR |
(+)- | camphene | FL/FR |
1,2- | dimethyl propyl 2-butenoate | |
(-)-gamma- | elemene | |
alpha- | elemol | FL/FR |
| furfuryl thenyl ether | |
3-(2- | furyl) acrolein | 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 |
alpha- | thujene | |
| tricyclene-9-butenone | |
2,4,4- | trimethyl-1,3-oxathiane | FL |
2,2,4- | trimethyl-1,3-oxathiane | |
balsamic |
| fir balsam absolute replacer | FL/FR |
camphoreous |
| camphene | FL/FR |
| camphor tree bark oil | 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 |
homo | menthyl acetate | 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 2-methyl butyrate | FL/FR |
| butyl heptanoate | FL/FR |
(Z)-3- | hexen-1-yl (E)-2-hexenoate | 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- | hepten-1-ol | FL/FR |
(Z)-3- | hexen-1-ol | FL/FR |
| hexyl butyrate | FL/FR |
4- | methyl-2-pentenal | FL |
iso | propyl tiglate | FL/FR |
| thiogeraniol | FL/FR |
3,5,5- | trimethyl hexanol | FL/FR |
herbal |
| coriander seed oil terpeneless | FL/FR |
iso | dihydrolavandulal | FL/FR |
| laurus nobilis leaf oil | FL/FR |
mentholic |
| cornmint oil | FL/FR |
| cornmint oil terpeneless | FL/FR |
| peppermint cyclohexanone | FL/FR |
minty |
1,8- | cineole | FL/FR |
| cornmint oil china | FL/FR |
| diosphenol | FL/FR |
homo | menthol | FL/FR |
(±)-iso | menthone | FL/FR |
(-)- | menthone | FL/FR |
| mint flavor | FL |
| myrtenol | FL/FR |
| pennyroyal oil | FL/FR |
| pennyroyal oil fractions | FL/FR |
| peppermint absolute | FL/FR |
| peppermint distillates | FL/FR |
| peppermint flavor | FL |
| peppermint oil idaho | FL/FR |
| peppermint oil special fractions | FL/FR |
| peppermint oil terpeneless | FL/FR |
| peppermint oil willamette | FL/FR |
laevo- | piperitone | FL/FR |
| piperitone | FL/FR |
dextro- | piperitone | FL/FR |
(-)-iso | pulegol | 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 |
sweet |
| orris rhizome absolute (iris germanica) | 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 |
| humulus lupulus extract | FL/FR |
| longifolene | FL/FR |
iso | pulegyl acetate | FL/FR |
|
Potential Uses:
Occurrence (nature, food, other): note
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 | iso | pulegol 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. |
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