isopulegol
p-menth-8-en-3-ol
 
Notes:
Various stereoisomers occur in essential oils. Flavouring agent
  • Berjé
    • Berje Inc.
      The solution is clear
      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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      Flavor Ingredients
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      Happening at Berje
      Product(s):
      isoPulegol
       
  • CTC Organics
    • CTC Organics
      For More Than 40 Year
      Your source for rare aroma chemicals for the flavor and fragrance industy.
      “The world is run by middle men.” The number of times I have heard Dr. Liu utter those words are innumerable. He loved reciting and recording famous quotes and had many of his own. Among his many talents, Dr. Liu had a unique genius in the area of chemistry. He had an uncanny understanding of the pulse of the chemical industry and was a superb salesman.
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      US Fax: (404) 577-1651
      Resources
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      Product(s):
      W0911 isopulegol
       
  • Moellhausen
    • Moellhausen S.P.A.
      THE CHEMISTRY OF EMOTIONS
      Innovation and commitment in the name of excellence.
      After 50 years in business, Moellhausen stands out as one of the world’s leading family-run companies in the industry of flavors and fragrances, raw materials, and specialties. My personal history is inextricably bound to that of the company, and I continue to dedicate all my energy to it along with our partners and collaborators who have supported us thus far with dedication, passion, love, and experience. Continuous investments and a professionalism aimed at achieving the highest levels of performance in service and quality, along with that same dedication, passion, love, and experience, have together enabled us to reach the absolute avant-garde level that characterizes Moellhausen today, recognized worldwide for its modernity, innovation, creativity, and respect for the environment and the safety and rights of those who work with us. As President and CEO of the company for 32 years, I offer a well-deserved thank you to all of our numerous customers, suppliers, employees, and company friends for helping to sustain our unstoppable and honorable growth. And it is with the support of all of our stakeholders that we will confidently continue to pursue our commitment to further advancing the excellence that our industry demands.
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      Product(s):
      1000055 isoPULEGOL
       
  • Penta International
    • Penta International Corporation
      Chemistry innovation
      At Penta, our products and services help businesses do business better.
      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
      US Email: Technical Services
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      Product(s):
      09-60010 L-isoPULEGOL, Kosher
       
Synonyms   Articles   Notes   Search
5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol (Click)
CAS Number: 7786-67-6Picture of molecule
ECHA EINECS - REACH Pre-Reg: 232-102-8
Nikkaji Web: J36.816D
XlogP3-AA: 3.00 (est)
Molecular Weight: 154.25266000
Formula: C10 H18 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
FEMA Number: 2962  isopulegol
FDA Mainterm: ISOPULEGOL
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
Synonyms   Articles   Notes   Search   Top
Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 197.00 to  198.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.099000 mm/Hg @ 25.00 °C. (est)
Flash Point: 173.00 °F. TCC ( 78.30 °C. ) (est)
logP (o/w): 2.724 (est)
Soluble in:
 alcohol
 water, 308.6 mg/L @ 25 °C (est)
Insoluble in:
 water
Synonyms   Articles   Notes   Search   Top
Organoleptic Properties:
Odor Type: minty
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 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)
 minty  cooling  herbal  peppermint  
Taste Description:
at 30.00 ppm.  
Minty cooling, herbaceous peppermint nuance
Mosciano, Gerard P&F 15, No. 6, 35, (1990)
Substantivity: 28 Hour(s)
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: masking agents
Synonyms   Articles   Notes   Search   Top
Suppliers:
Berjé
isoPulegol
Happening at Berje
Citrus and Allied Essences
isoPulegol Extra FCC
Market Report
Coompo
For experimental / research use only.
isoPulegol from Plants ≥98%
Odor: characteristic
Use: Isopulegol is a monoterpene alcohol intermediate in the preparation of (-)-menthol and it is present in the essential oils of various plants. This work presents behavioral effects of isopulegol in animal models of open field, elevated plus maze (EPM), rota rod, hole board, barbiturate-induced sleeping time, tail suspension and forced swimming tests in mice. Isopulegol was administered intraperitoneally to male mice at single doses of 25 and 50 mg/kg, while diazepam 1 or 2 mg/kg and imipramine 10 or 30 mg/kg were used as standard drugs. The results showed that, similar to diazepam (1 mg/kg), both doses of isopulegol significantly modified all the observed parameters in the EPM test, without alter the general motor activity in the open field test. In the same way, both doses of isopulegol increased the number of head dips in the hole-board test. Forced swimming and tail suspension tests showed that isopulegol (25 and 50 mg/kg) was able to induce a significant increase in the immobility time, in opposite to imipramine, a recognized antidepressant drug. There was a decrease in the sleep latency time and prolongation of the pentobarbital-induced sleeping time with both doses of Isopulegol. Different from diazepam (2 mg/kg), isopulegol (25 e 50 mg/kg) had no effect on the motor coordination of animals in the rota rod test. These results showed that isopulegol presented depressant- and anxiolytic-like effects. The anticonvulsant and bioprotective effects of isopulegol against PTZ-induced convulsions are possibly related to positive modulation of benzodiazepine-sensitive GABAA receptors and to antioxidant properties.
CTC Organics
isopulegol
Diffusions Aromatiques
isoPULEGOL
Global Essence
isoPulegol
Moellhausen
isoPULEGOL
PCAS
isoPulegol, Kosher
Penta International
L-isoPULEGOL, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
isoPulegol
TCI AMERICA
For experimental / research use only.
isoPulegol >90.0%(GC)
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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
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: --
Synonyms   Articles   Notes   Search   Top
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
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 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
HMDB (The Human Metabolome Database): HMDB36077
FooDB: FDB014911
Export Tariff Code: 2905.22.5050
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
For Odor
citrus
 bergamot acetoacetateFR
 thiogeraniolFL/FR
herbal
 buchu oximeFR
mentholic
 cornmint oil terpenelessFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
 peppermint cyclohexanoneFL/FR
dextro-piperitoneFL/FR
isopulegyl acetateFL/FR
minty
 diosphenolFL/FR
(-)-menthoneFL/FR
 pennyroyal oilFL/FR
 peppermint oil idahoFL/FR
 peppermint oil terpenelessFL/FR
isopulegoneFL/FR
(R)-(+)-pulegoneFL/FR
sulfurous
 buchu mercaptanFL/FR
 mango thiolFL/FR
 passiflora acetateFL/FR
 
For Flavor
 
No flavor group found for these
 diosphenolFL/FR
dextro-piperitoneFL/FR
isopulegoneFL/FR
cooling
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
green
 potato butyraldehydeFL
mentholic
 cornmint oil terpenelessFL/FR
 peppermint cyclohexanoneFL/FR
minty
(-)-menthoneFL/FR
 pennyroyal oilFL/FR
 peppermint oil idahoFL/FR
 peppermint oil terpenelessFL/FR
(R)-(+)-pulegoneFL/FR
 thiogeraniolFL/FR
sulfurous
 buchu mercaptanFL/FR
 mango thiolFL/FR
tropical
 passiflora acetateFL/FR
woody
isopulegyl acetateFL/FR
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
 apricotFR
 caramelFL
 cherryFR
 citronellaFL/FR
 eucalyptusFL/FR
 geraniumFR
 herbalFR
 lemongrassFR
 mandarinFR
 mintFR
 oral care agents 
 peachFR
 pennyroyalFL/FR
 peppermintFR
 plumFR
 raspberryFR
 rose leafFL/FR
 spearmintFR
 tuberoseFR
Synonyms   Articles   Notes   Search   Top
Occurrence (nature, food, other): note
 angelica seed oil CO2 extract @ 1.40%
Data  GC  Search Trop  Picture
 bergamot oil @ 0.000-0.004%
Data  GC  Search Trop  Picture
 cascarilla bark oil @ 0.05%
Data  GC  Search Trop  Picture
 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 3.80%
Data  GC  Search Trop  Picture
 eucalyptus citriadora
Search Trop  Picture
 eucalyptus citriodora oil @ 3.41%
Data  GC  Search Trop  Picture
 eucalyptus globulus oil pakistan @ 0.20%
Data  GC  Search Trop  Picture
 geranium
Search Trop  Picture
 grapefruit oil c.p. @ 0.05%
Data  GC  Search Trop  Picture
 grapefruit oil c.p. @ 0.06%
Data  GC  Search Trop  Picture
 grapefruit oil c.p. italy @ 0.04%
Data  GC  Search Trop  Picture
 laurel leaf oil turkey @ 0.10%
Data  GC  Search Trop  Picture
 lemon verbena oil morocco @ 0.7%
Data  GC  Search Trop  Picture
 lemongrass
Search  Picture
 lemongrass oil @ 0.26%
Data  GC  Search Trop  Picture
 lemongrass oil @ 1.23%
Data  GC  Search Trop  Picture
 lemongrass oil morocco @ 0.30%
Data  GC  Search Trop  Picture
 lime oil distilled peru @ 0.08%
Data  GC  Search Trop  Picture
 mandarin
Search Trop  Picture
 mandarin oil italy @ trace%
Data  GC  Search Trop  Picture
 mint
Search  Picture
 pennyroyal oil @ trace%
Data  GC  Search Trop  Picture
 petitgrain combava oil @ 0.32%
Data  GC  Search  Picture
 petitgrain grapefruit oil @ 0.60%
Data  GC  Search Trop  Picture
 petitgrain lime oil @ 0.10%
Data  GC  Search Trop  Picture
 petitgrain sweet oil @ 0.51%
Data  GC  Search  Picture
 pseudotsuga menziesii
Search Trop  Picture
 pteronia oil @ 0.10%
Data  GC  Search Trop  Picture
 rum
Search  Picture
 sage oil england @ 0.10%
Data  GC  Search Trop  Picture
 wormseed oil spain @ 3.54%
Data  GC  Search Trop  Picture
Synonyms   Articles   Notes   Search   Top
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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