isopulegol
p-menth-8-en-3-ol
 
Notes:
Various stereoisomers occur in essential oils. Flavouring agent
  • Berjé
    • Berje Inc.
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      Where the world comes to its senses - Berjé is a global distributor of Essential Oils and Aromatic Chemicals.
      Berjé is a family-owned business that has been in operation for six decades. The company's origins and strength lie in a profound understanding of the supply and the quality of the diverse raw materials consumed by the flavor and fragrance industries. This base was expanded upon more than two decades ago to include fragrance production. The company's unparalleled raw material expertise is focused on the supply of essential oils and aromatic chemicals. This is supported by our long-standing relationships with a worldwide fabric of producers ensuring the greatest prospects for uninterrupted supply in markets that are often volatile and unpredictable.
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  • CJ Latta & Associates
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  • Global Essence
    • Global Essence Inc.
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      Accommodate each customers unique needs.
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    • Penta International Corporation
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  • Synerzine
    • Synerzine, Inc.
      Innovation. Customization. Aroma Ingredients.
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      Synerzine expresses what we have grown to embody as an organization - the synergy and connection between raw ingredients, science, technology, and the final product. Our experienced team is passionate about bringing our customers high-quality innovative ingredients that they can trust.
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  • TCI AMERICA
    • TCI AMERICA
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      M0320 isoPulegol >90.0%(GC)
      SDS
       
Synonyms   Articles   Notes   Search
CAS Number: 7786-67-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 232-102-8
FDA UNII: Search
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, Edge 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:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):89-79-2 ; 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.
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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
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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:
CosIng: cosmetic data
Cosmetic Uses: fragrance
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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)
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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
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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 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: --
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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
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Substances Added to Food (formerly 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
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Potential Blenders and core components note
 
For Odor
No odor group found for these
(-)-gamma-elemene 
alliaceous
 dibutyl sulfideFL/FR
balsamic
 betula pubescens bud oilFL/FR
 fir balsam absoluteFR
 fir balsam absolute replacerFL/FR
 fir balsam concreteFR
camphoreous
 camphor tree bark oilFL/FR
 eucalyptus polybractea oilFR
citrus
 bergamot acetoacetateFR
 elemi oil replacerFR
 lemon balm fragranceFR
 lemongrass fragranceFR
 lemongrass oilFL/FR
 lemongrass oil replacerFR
 lime oil fractionsFR
 litsea cubeba fruit oilFL/FR
 melissa oil replacerFR
alpha-methylene citronellalFR
 neroli ketoneFR
dry
 autumn specialtyFR
floral
 coriander seed oil terpenelessFL/FR
 dihydrocarvyl acetateFL/FR
 glycoacetalFR
 karo karounde absoluteFR
 karo karounde absolute replacerFR
 linaloolFL/FR
 melaleuca ericifolia leaf oilFR
 mimosa absoluteFL/FR
 mimosa absolute franceFL/FR
 mimosa absolute indiaFL/FR
 mimosa absolute moroccoFL/FR
 mimosa absolute replacerFR
 mimosa fragranceFR
 mimosa specialtyFR
 orange leaf absoluteFL/FR
 orris rhizome absolute (iris germanica)FL/FR
fruity
 butyl 2-methyl butyrateFL/FR
 cyclohexyl crotonateFR
1,4-dibutyl-6,8-dioxabicyclo(3.2.1)octaneFR
1,4-diisopropyl-6,8-dioxabicyclo(3.2.1)octaneFR
1,2-dimethyl propyl 2-butenoate 
 grapefruit acetalFR
(Z)-3-hexen-1-yl isobutyrateFL/FR
2-methyl-2-pentenalFL/FR
 prenyl ethyl etherFL/FR
 alfalfa absoluteFR
 alfalfa oilFL/FR
 alfalfa resinoidFL/FR
 bark carbaldehydeFR
 bergoxaneFR
 bicyclogermacrene 
 butyl heptanoateFL/FR
sec-butyl-3-methyl but-2-ene thioateFL/FR
 citral / diisotridecyl acetalFR
3,7-dimethyl-6-octenoic acidFL/FR
 elemi specialtyFR
alpha-elemolFL/FR
 forest fragranceFR
 fresh nitrileFR
 galbanum oleoresinFL/FR
 galbanum resinoidFL/FR
 galbanum resinoid replacerFR
 green fragranceFR
 green specialtyFR
(Z)-3-hepten-1-olFL/FR
3-hepten-2-oneFL/FR
(Z)-3-hexen-1-olFL/FR
(Z)-3-hexen-1-yl (E)-2-hexenoateFL/FR
 hexyl butyrateFL/FR
 hexyl hexanoateFL/FR
 thiogeraniolFL/FR
 tricyclene-9-butenone 
3,5,5-trimethyl hexanolFL/FR
2,2,4-trimethyl-1,3-oxathiane 
herbal
 buchu oximeFR
(+)-alpha-campholenic aldehydeFL/FR
 camphor wood oil decamphorisedFR
 canarium luzonicum oilFL/FR
1,8-cineoleFL/FR
1,4-cineoleFL/FR
 clary sage resin americaFR
isodihydrolavandulalFL/FR
6-hydroxydihydrotheaspirane (mixture of isomers)FL/FR
 laurus nobilis leaf oilFL/FR
 myrtenolFL/FR
 nonisyl formateFR
 oregano specialtyFR
 piperitoneFL/FR
 sabinene hydrateFL/FR
 theaspiraneFL/FR
 tricyclo(5.2.1.02,6)dec-3-enyl acetateFR
leafy
 autumn fragranceFR
medicinal
meta-dimethyl hydroquinoneFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil chinaFL/FR
 cornmint oil terpenelessFL/FR
laevo-mentholFL/FR
dextro,laevo-mentholFL/FR
(±)-isomenthoneFL/FR
 menthyl acetate racemicFL/FR
 peppermint cyclohexanoneFL/FR
dextro-piperitoneFL/FR
isopulegyl acetateFL/FR
minty
dextro-dihydrocarvoneFL/FR
 diosphenolFL/FR
homomentholFL/FR
(-)-menthoneFL/FR
homomenthyl acetateFL/FR
laevo-menthyl lactateFL/FR
 mint fragranceFR
 mint specialtyFR
 pennyroyal oilFL/FR
 pennyroyal oil fractionsFL/FR
 peppermint absoluteFL/FR
 peppermint distillatesFL/FR
 peppermint fragranceFR
 peppermint oil americaFL/FR
 peppermint oil idahoFL/FR
 peppermint oil special fractionsFL/FR
 peppermint oil terpenelessFL/FR
 peppermint oil willametteFL/FR
laevo-piperitoneFL/FR
isopropyl tiglateFL/FR
(-)-isopulegolFL/FR
isopulegoneFL/FR
(R)-(+)-pulegoneFR
2,4,4,6-tetramethyl cyclohexa-2,5-diene-1-oneFR
phenolic
4-methyl-2,6-dimethoxyphenolFL/FR
pine
 pine oil 85FR
spicy
 clove bud oilFL/FR
2,5-dimethyl bicyclo(3.2.1)-2-octen-3-yl acetate + 1,4-dimethyl bicyclo(3.2.1)-2-octen-3-yl acetateFR
3-(2-furyl) acroleinFL/FR
 laurel leaf oil replacerFR
2-octanolFL/FR
black pepper oil CO2 extractFL/FR
 tea tree oilFR
sulfurous
 buchu mercaptanFL/FR
 mango thiolFL/FR
 passiflora acetateFL/FR
terpenic
 juniper branch oilFR
alpha-phellandreneFL/FR
woody
 bruyere root absoluteFR
(+)-campheneFL/FR
 campheneFL/FR
 costus specialtyFR
alpha-farneseneFL/FR
alpha-farnesene isomerFL/FR
 furfuryl thenyl ether 
 humulus lupulus extractFL/FR
 juniper fragranceFR
 longifoleneFL/FR
 moss naphthaleneolFR
(±)-tetrahydronootkatoneFL/FR
alpha-thujene 
 xanthoxylum alatum roxb. oilFR
 
For Flavor
 
No flavor group found for these
2-acetyl-4-isopropenyl pyridineFL
2-acetyl-4-isopropyl pyridineFL
 betula pubescens bud oilFL/FR
 bicyclogermacrene 
sec-butyl-3-methyl but-2-ene thioateFL/FR
(+)-campheneFL/FR
1,2-dimethyl propyl 2-butenoate 
(-)-gamma-elemene 
alpha-elemolFL/FR
 furfuryl thenyl ether 
3-(2-furyl) acroleinFL/FR
2-heptenoic acidFL
(Z)-3-hexenoic acidFL
 menthyl acetate racemicFL/FR
3-(methyl thio) hexanalFL
(E,E)-3,5-octadien-2-oneFL
 prenyl ethyl etherFL/FR
isopulegoneFL/FR
(±)-tetrahydronootkatoneFL/FR
alpha-thujene 
 tricyclene-9-butenone 
2,4,4-trimethyl-1,3-oxathianeFL
2,2,4-trimethyl-1,3-oxathiane 
balsamic
 fir balsam absolute replacerFL/FR
camphoreous
 campheneFL/FR
 camphor tree bark oilFL/FR
6-hydroxydihydrotheaspirane (mixture of isomers)FL/FR
chemical
meta-dimethyl hydroquinoneFL/FR
citrus
 lemongrass oilFL/FR
 linaloolFL/FR
 litsea cubeba fruit oilFL/FR
cooling
1,4-cineoleFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
homomenthyl acetateFL/FR
laevo-menthyl lactateFL/FR
 peppermint oil americaFL/FR
 sabinene hydrateFL/FR
 theaspiraneFL/FR
 WS-3FL
creamy
3-hepten-2-oneFL/FR
floral
 dihydrocarvyl acetateFL/FR
3,7-dimethyl-6-octenoic acidFL/FR
 mimosa absolute moroccoFL/FR
 orange leaf absoluteFL/FR
fruity
 butyl 2-methyl butyrateFL/FR
 butyl heptanoateFL/FR
(Z)-3-hexen-1-yl (E)-2-hexenoateFL/FR
(Z)-3-hexen-1-yl isobutyrateFL/FR
 hexyl hexanoateFL/FR
2-methyl-2-pentenalFL/FR
green
 alfalfa oilFL/FR
 alfalfa resinoidFL/FR
(+)-alpha-campholenic aldehydeFL/FR
 canarium luzonicum oilFL/FR
 dibutyl sulfideFL/FR
dextro-dihydrocarvoneFL/FR
alpha-farneseneFL/FR
alpha-farnesene isomerFL/FR
 galbanum oleoresinFL/FR
 galbanum resinoidFL/FR
(Z)-3-hepten-1-olFL/FR
(Z)-3-hexen-1-olFL/FR
 hexyl butyrateFL/FR
4-methyl-2-pentenalFL
isopropyl tiglateFL/FR
 thiogeraniolFL/FR
3,5,5-trimethyl hexanolFL/FR
herbal
 coriander seed oil terpenelessFL/FR
isodihydrolavandulalFL/FR
 laurus nobilis leaf oilFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil terpenelessFL/FR
 peppermint cyclohexanoneFL/FR
minty
1,8-cineoleFL/FR
 cornmint oil chinaFL/FR
 diosphenolFL/FR
homomentholFL/FR
(±)-isomenthoneFL/FR
(-)-menthoneFL/FR
 mint flavorFL
 myrtenolFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil fractionsFL/FR
 peppermint absoluteFL/FR
 peppermint distillatesFL/FR
 peppermint flavorFL
 peppermint oil idahoFL/FR
 peppermint oil special fractionsFL/FR
 peppermint oil terpenelessFL/FR
 peppermint oil willametteFL/FR
laevo-piperitoneFL/FR
 piperitoneFL/FR
dextro-piperitoneFL/FR
(-)-isopulegolFL/FR
orris
 costus root oilFL
phenolic
4-methyl-2,6-dimethoxyphenolFL/FR
spicy
 clove bud oilFL/FR
2-octanolFL/FR
black pepper oil CO2 extractFL/FR
sulfurous
 buchu mercaptanFL/FR
 mango thiolFL/FR
sweet
 orris rhizome absolute (iris germanica)FL/FR
terpenic
alpha-phellandreneFL/FR
tropical
 passiflora acetateFL/FR
vegetable
 potato butyraldehydeFL
waxy
 mimosa absoluteFL/FR
 mimosa absolute franceFL/FR
 mimosa absolute indiaFL/FR
 humulus lupulus extractFL/FR
 longifoleneFL/FR
isopulegyl acetateFL/FR
 
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Potential Uses:
 apricotFR
 caramelFL
 cherryFR
 citronellaFR
 eucalyptus oil replacerFR
 geraniumFR
 herbalFR
 lemongrassFR
 mandarinFR
 mintFR
 oral care agents 
 peachFR
 pennyroyalFL/FR
 peppermintFR
 plumFR
 raspberryFR
 rose leafFL/FR
 spearmintFR
 tuberoseFR
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Occurrence (nature, food, other): note
 angelica seed oil CO2 extract @ 1.40%
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 bergamot oil @ 0.000-0.004%
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 cascarilla bark oil @ 0.05%
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 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 3.80%
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 eucalyptus citriadora
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 eucalyptus citriodora oil @ 3.41%
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 eucalyptus globulus oil pakistan @ 0.20%
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 geranium
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 grapefruit oil c.p. @ 0.05%
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 grapefruit oil c.p. @ 0.06%
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 grapefruit oil c.p. italy @ 0.04%
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 laurel leaf oil turkey @ 0.10%
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 lemon verbena oil morocco @ 0.7%
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 lemongrass
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 lemongrass oil @ 0.26%
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 lemongrass oil @ 1.23%
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 lemongrass oil morocco @ 0.30%
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 lime oil distilled peru @ 0.08%
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 mandarin
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 mandarin oil @ trace%
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 mandarin oil italy @ trace%
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 mint
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 pennyroyal oil @ trace%
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 petitgrain combava oil @ 0.32%
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 petitgrain grapefruit oil @ 0.60%
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 petitgrain lime oil @ 0.10%
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 petitgrain sweet oil @ 0.51%
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 pseudotsuga menziesii
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 pteronia oil @ 0.10%
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 rum
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 sage oil england @ 0.10%
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 wormseed oil spain @ 3.54%
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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
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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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