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: | Yes |
Specific Gravity: | 0.90400 to 0.91300 @ 25.00 °C.
|
Pounds per Gallon - (est).: | 7.522 to 7.597
|
Refractive Index: | 1.46800 to 1.47700 @ 20.00 °C.
|
Melting Point: | 78.00 °C. @ 760.00 mm Hg
|
Boiling Point: | 216.00 to 218.00 °C. @ 760.00 mm Hg
|
Boiling Point: | 91.00 °C. @ 12.00 mm Hg
|
Acid Value: | 1.00 max. KOH/g
|
Vapor Pressure: | 0.099000 mmHg @ 25.00 °C. (est) |
Flash Point: | 195.00 °F. TCC ( 90.56 °C. )
|
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 |
Odor Description: at 10.00 % in dipropylene glycol. | minty cooling medicinal woody Luebke, William tgsc, (2017) |
|
|
Flavor Type: minty |
|
| minty cooling mentholic peppermint grassy herbal tropical |
Taste Description:
| minty cooling mentholic peppermint grassy herbal tropical Luebke, William tgsc, (2017) |
|
Odor and/or flavor descriptions from others (if found). |
|
Symrise |
Isopulegol |
Taste Description: | minty, cooling, slightly fruity Useful in: mint, fruity citrus, fruity red, sweet others. |
|
|
Cosmetic Information:
Suppliers:
Augustus Oils |
Iso Pulegol
|
Services |
Aurochemicals |
isoPULEGOL, Natural
|
BOC Sciences |
For experimental / research use only. |
isoPULEGOL 95%
|
Ernesto Ventós |
ISOPULEGOL
Odor: MINTHY, HERBAL, SWEET-BITTER |
ExtraSynthese |
For experimental / research use only. |
(-)-isoPulegol (GC) ≥99%
|
Indukern F&F |
ISOPULEGOL
Odor: HERBAL, LICORICE |
Lipo Chemicals |
Coolact® P
Odor: characteristic Use: Coolact® P is a sensory agent that provides a cooling effect to the skin. The product functions by directly stimulating the receptors at the nerve endings of the skin to produce a cooling sensation. Coolact® P provides a similar cooling effect to Menthol but without the Menthol odor. |
Lluch Essence |
ISOPULEGOL NATURAL EX- EUCALYPTUS CIT.
|
Nagar Haveli Perfumes & Aromatics |
Iso Pulegol
Natural Odor: Minty cooling medicinal woody |
Natural Advantage |
Isopulegol Nat
Flavor: cooling, fresh, herbaceous, minty |
Riverside Aromatics LTD.is the exclusive distributor for Europe in UK for any non-US based inquiries |
Natural Advantage |
Isopulegol, laevo- Nat
Flavor: cooling, fresh, herbaceous, minty |
OQEMA |
isoPulegol
|
Penta International |
DL-ISOPULEGOL
|
Penta International |
ISOPULEGOL NATURAL
|
Reincke & Fichtner |
isoPulegol
|
Riverside Aromatics |
isoPULEGOL, NATURAL
|
Sigma-Aldrich |
(-)-Isopulegol, ≥98%
Odor: minty |
Certified Food Grade Products |
Synerzine |
isoPulegol
|
Takasago |
Coolact® P
|
The Fragrance Museum |
Vigon International |
Isopulegol Purified
Odor: RATHER HARSH, CAMPHORACEOUS AND MINTY ODOR, WITH A ROSELEAF AND GERANIUM BACKGROUND |
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. |
Human Experience: |
8 % solution: no irritation or sensitization. |
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 |
Recommendation for (-)-isopulegol usage levels up to: | | 6.0000 % in the fragrance concentrate.
|
|
Maximised Survey-derived Daily Intakes (MSDI-EU): | 850.00 (μg/capita/day) |
Maximised Survey-derived Daily Intakes (MSDI-USA): | 3300.00 (μg/capita/day) |
Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3900 (μg/person/day) |
Threshold of Concern: | 1800 (μg/person/day) |
Structure Class: | I |
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: | - | - |
|
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). |
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. |
| average usage mg/kg | maximum usage mg/kg |
Dairy products, excluding products of category 02.0 (01.0): | 12.00000 | 15.00000 |
Fats and oils, and fat emulsions (type water-in-oil) (02.0): | - | - |
Edible ices, including sherbet and sorbet (03.0): | - | - |
Processed fruit (04.1): | - | - |
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - |
Confectionery (05.0): | 10.00000 | 50.00000 |
Chewing gum (05.0): | - | - |
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 50.00000 | 100.00000 |
Bakery wares (07.0): | 5.00000 | 20.00000 |
Meat and meat products, including poultry and game (08.0): | 14.00000 | 19.00000 |
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | - | - |
Eggs and egg products (10.0): | - | - |
Sweeteners, including honey (11.0): | - | - |
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | - | - |
Foodstuffs intended for particular nutritional uses (13.0): | - | - |
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | - | - |
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | - | - |
Ready-to-eat savouries (15.0): | - | - |
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | - | - |
Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s): |
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients. View pdf |
European Food Safety Athority(EFSA): | Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
European Food Safety Authority (EFSA) reference(s): |
Flavouring Group Evaluation 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting) View page or View pdf |
Statement on List of Representative Substances for Testing.
The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000). View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 57, Revision 1 (FGE.57Rev1): consideration of isopulegone and three flavouring substances evaluated by JECFA (55th meeting) View page or View pdf |
Safety and efficacy of oct-1-en-3-ol, pent-1-en-3-ol, oct-1-en-3-one, oct-1-en-3-yl acetate, isopulegol and 5-methylhept-2-en-4-one, belonging to chemical group 5 and of isopulegone and a-damascone belonging to chemical group 8 when used as flavourings for all animal species View page or View pdf |
EPI System: | View |
AIDS Citations: | Search |
Cancer Citations: | Search |
Toxicology Citations: | Search |
EPA Substance Registry Services (TSCA): | 89-79-2 |
EPA ACToR: | Toxicology Data |
EPA Substance Registry Services (SRS): | Registry |
Laboratory Chemical Safety Summary : | 7057942 |
National Institute of Allergy and Infectious Diseases: | Data |
WGK Germany: | 2 |
| (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol |
Chemidplus: | 0000089792 |
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 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 |
| 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 |
| 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 |
| 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 |
| canarium luzonicum oil | FL/FR |
1,4- | cineole | FL/FR |
| clary sage resin america | FR |
iso | dihydrolavandulal | FL/FR |
6- | hydroxydihydrotheaspirane (mixture of isomers) | FL/FR |
spike | lavender 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 |
medicinal |
meta- | dimethyl hydroquinone | FL/FR |
mentholic |
| cornmint oil china | FL/FR |
| cornmint oil terpeneless | FL/FR |
(±)- | menthol | FL/FR |
laevo- | menthol | FL/FR |
dextro,laevo- | menthol | FL/FR |
dextro-neo | menthol | FL/FR |
(±)-iso | menthone | FL/FR |
laevo- | menthyl acetate | FL/FR |
| menthyl acetate racemic | FL/FR |
| peppermint cyclohexanone | FL/FR |
dextro- | piperitone | FL/FR |
iso | pulegyl acetate | FL/FR |
minty |
| cornmint oil japan | FL/FR |
dextro- | dihydrocarvone | FL/FR |
| diosphenol | FL/FR |
homo | menthol | FL/FR |
(±)- | menthone | 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 |
(R)-(+)- | pulegone | FR |
iso | 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 |
3-(2- | furyl) acrolein | FL/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 |
| furfuryl thenyl ether | |
| humulus lupulus extract | FL/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 | |
| furfuryl thenyl ether | |
3-(2- | furyl) acrolein | FL/FR |
(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 |
alpha- | thujene | |
| tricyclene-9-butenone | |
2,2,4- | trimethyl-1,3-oxathiane | |
2,4,4- | trimethyl-1,3-oxathiane | FL |
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 |
spike | lavender oil | FL/FR |
dextro,laevo- | menthol | FL/FR |
iso | menthol | FL |
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 2-methyl butyrate | FL/FR |
| 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 |
| thiogeraniol | FL/FR |
3,5,5- | trimethyl hexanol | FL/FR |
herbal |
iso | dihydrolavandulal | FL/FR |
mentholic |
| cornmint oil terpeneless | FL/FR |
dextro-neo | menthol | FL/FR |
(±)- | menthol | FL/FR |
| peppermint cyclohexanone | FL/FR |
minty |
| cornmint oil china | FL/FR |
| cornmint oil japan | FL/FR |
| diosphenol | FL/FR |
homo | menthol | FL/FR |
(±)- | menthone | FL/FR |
(±)-iso | menthone | FL/FR |
(-)- | menthone | FL/FR |
laevo- | menthyl acetate | 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 |
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 |
| humulus lupulus extract | FL/FR |
| longifolene | FL/FR |
iso | pulegyl acetate | FL/FR |
|
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| coolact P (Takasago) | | koolada-OBMA synthetic | (1R,3R,4S)-p- | menth-8-en-3-ol | (1R,3R,4S)-para- | menth-8-en-3-ol | p-8,9- | menthen-3-ol | p-8(9)- | menthen-3-ol | para-8,9- | menthen-3-ol | para-8(9)- | menthen-3-ol | (1R-(1alpha,2beta,5alpha))-5- | methyl-2-(1-methyl ethenyl) cyclohexanol | (1R,2S,5R)-5- | methyl-2-(1-methyl ethenyl) cyclohexanol | (1R-(1alpha,2beta,5alpha))-5- | methyl-2-(1-methylethenyl)cyclohexanol | (1R,2S,5R)-5- | methyl-2-(1-methylethenyl)cyclohexanol | (1R,2R,5S)-5- | methyl-2-prop-1-en-2-ylcyclohexan-1-ol | (1R,2R,5S)-2-iso | propenyl-5-methyl cyclohexanol | (-)-L-iso | pulegol | (-)-laevo-iso | pulegol | 1R,2S,5R-iso | pulegol | L-iso | pulegol | laevo-iso | pulegol | iso | pulegol purified |
Articles:
PubMed: | Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants. |
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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