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

(-)-isopulegol
1R,2S,5R-isopulegol

Sponsors

Fragrance Demo Formulas
Name:(1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
CAS Number: 89-79-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-940-6
FDA UNII:3TH92O3BXN
Nikkaji Web:J1.523.142D
Beilstein Number:1906573
MDL:MFCD00134655
CoE Number:2033
XlogP3-AA:3.00 (est)
Molecular Weight:154.25266000
Formula:C10 H18 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Register name to be changed to 1R,2S,5R-isopulegone. According to the JECFA: Min. assay value is "95 % (total of isomers; <1 % citronellal)". Composition of mixture not specified.
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
JECFA Food Flavoring:755 isopulegol
FLAVIS Number:02.067 (Old)
DG SANTE Food Flavourings:02.067 1R,2S,5R-isopulegol
FEMA Number:2962 isopulegol
FDA:No longer provide for the use of these seven synthetic flavoring substances
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: 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 mm/Hg @ 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
Odor sample from: Sigma-Aldrich
Flavor Type: minty
">minty cooling mentholic peppermint grassy herbal tropical
Taste Description: minty cooling mentholic peppermint grassy herbal tropical
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:
CosIng:cosmetic data
Cosmetic Uses: masking agents
 
Suppliers:
Aurochemicals
isoPULEGOL, Natural
BOC Sciences
For experimental / research use only.
isoPULEGOL 95%
CG Herbals
isoPulegol
Odor: Comphoraceous Minty
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 85%
Nagar Haveli Perfumes & Aromatics
Iso Pulegol
Natural
Odor: Minty cooling medicinal woody
Natural Advantage
Isopulegol Nat
Natural Advantage
levo-Isopulegol Nat
OQEMA
isoPulegol
Penta International
DL-isoPULEGOL, Kosher
Reincke & Fichtner
isoPulegol
Riverside Aromatics
isoPULEGOL, NATURAL
Sigma-Aldrich
(-)-Isopulegol, ≥98%
Odor: minty
Certified Food Grade Products
Symrise
Isopulegol
Flavor: minty, cooling, slightly fruity
Useful in: mint, fruity citrus, fruity red, sweet others.
Synerzine
isoPulegol
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
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
 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: --
 
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/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 12.0000015.00000
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): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 50.00000100.00000
Bakery wares (07.0): 5.0000020.00000
Meat and meat products, including poultry and game (08.0): 14.0000019.00000
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:
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

EPI System: View
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:
Leffingwell:Chirality or Article
 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:89-79-2
Pubchem (cid):7057942
Pubchem (sid):135019731
 
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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB36078
FooDB:FDB014912
Export Tariff Code:2906.19.0000
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
1,4-
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
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
(±)-
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
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
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
spike
lavender oil
FL/FR
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
iso
menthol
FL
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
(±)-
menthol
FL/FR
dextro-neo
menthol
FL/FR
peppermint cyclohexanone
FL/FR
minty
cornmint oil china
FL/FR
cornmint oil japan
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
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:
FRapricot
FLcaramel
FRcherry
FRcitronella
FReucalyptus oil replacer
FRgeranium
FRherbal
FRlemongrass
FRmandarin
FRmint
 oral care agents
FRpeach
FL/FRpennyroyal
FRpeppermint
FRplum
FRraspberry
FL/FRrose leaf
FRspearmint
FRtuberose
 
Occurrence (nature, food, other):note
 cornmint oil
Search Trop Picture
 eucalyptus citriodora
Search Trop Picture
 hesperozygis rhododon
Search Trop Picture
 hesperozygis ringens
Search Trop Picture
 lemon balm shoot
Search Trop Picture
 lemon leaf oil
Search Trop Picture
 lemongrass plant
Search Trop Picture
 mandarin fruit
Search Trop Picture
 oregano shoot
Search Trop Picture
 pepper black pepper fruit
Search Trop Picture
 pepper black pepper seed
Search Trop Picture
 petitgrain lemon oil
Search Trop Picture
 rosemary plant
Search Trop Picture
 
Synonyms:
 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-isopropenyl-5-methyl cyclohexanol
(-)-L-isopulegol
(-)-laevo-isopulegol
1R,2S,5R-isopulegol
L-isopulegol
laevo-isopulegol
isopulegol 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.
 
Notes:
isolated from mentha cardiaca. Isol. from Mentha pulegium (European pennyroyal) and other essential oils
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