isopulegone
p-menth-8-en-3-one
Identification
| Name | isopulegone |
| IUPAC | 5-methyl-2-prop-1-en-2-ylcyclohexan-1-one |
| CAS Number | 29606-79-9 |
| EINECS | 249-725-6 |
| FDA UNII | 681XD66YSR |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| Nikkaji Number | J2.365.190D |
| CoE Number | 2051 |
Regulatory
| JECFA Food Flavoring | 754 isopulegone |
| DG SANTE Food Flavourings | 07.067 2R,5S-isopulegone |
| FEMA Number | 2964 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 29606-79-9 ; ISOPULEGONE |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92500 to 0.93200 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.697 to 7.755 |
| Refractive Index | 1.46500 to 1.47300 @ 20.00 °C. |
| Boiling Point | 101.00 to 102.00 °C. @ 17.00 mm Hg, 208.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.140000 mmHg @ 25.00 °C. (est) |
| Flash Point | 175.00 °F. TCC ( 79.44 °C. ) |
| logP (o/w) | 2.408 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Oral/Parenteral Toxicity | intravenous-dog LDLo 450 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nCARDIAC: CHANGE IN RATE']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for isopulegone usage levels up to | 1.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.012 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.01 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 2500 (μg/person/day) |
| Threshold of Concern | 540 (μg/person/day) |
| Structure Class | II |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| 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 | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
| Dairy products, excluding products of category 02.0 (01.0) | 6.40000 |
| 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) | 9.50000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | - |
| Bakery wares (07.0) | 6.10000 |
| Meat and meat products, including poultry and game (08.0) | 11.00000 |
| 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) | - |
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Potential Uses
Natural Occurrence
Synonyms
cyclohexanone, 2-isopropylideno-5-methyl-
cyclohexanone, 5-methyl-2-(1-methylethenyl)-
p-
menth-8-en-3-one
para-
menth-8-en-3-one
delta-8,9-p-
menthen-3-one
delta-8,9-para-
menthen-3-one
8(9)-p-
menthen-3-one, d-
trans-5-
methyl-2-(1-methyl vinyl) cyclohexan-1-one
trans-5-
methyl-2-(1-methylethenyl)cyclohexanone
trans-5-
methyl-2-(1-methylvinyl)cyclohexan-1-one
5-
methyl-2-(prop-1-en-2-yl)cyclohexan-1-one
5-
methyl-2-(prop-1-en-2-yl)cyclohexanone
5-
methyl-2-prop-1-en-2-ylcyclohexan-1-one
1-
methyl-4-isopropenyl-3-cyclohexanone
1-iso
propyl-4-methyl-2-cyclohexanone
iso
pulegon
(+)-cis-iso
pulegone
2R,5S-iso
pulegone
PubMed:
Effect of different growth stages of Ziziphora clinopodioides Lam. on its chemical composition.
PubMed:
Is differential use of Juniperus monosperma by small ruminants driven by terpenoid concentration?
PubMed:
Chemical composition of the essential oils of variegated pink-fleshed lemon (Citrus x limon L. Burm. f.) and their anti-inflammatory and antimicrobial activities.
PubMed:
Chemical composition and biological evaluation of essential oils of Pulicaria jaubertii.
PubMed:
[A new monoterpenoid glucoside from the twigs of Chamaecyparis obtusa var. breviramea f. crippsii].
PubMed:
Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham.
PubMed:
Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
PubMed:
Chemical composition, antimicrobial and antioxidant activities of the essential oil of Tibetan herbal medicine Dracocephalum heterophyllum Benth.
PubMed:
Genetic variability in Hesperozygis ringens Benth. (Lamiaceae), an endangered aromatic and medicinal plant of southern Brazil.
PubMed:
Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran.
PubMed:
New monoterpenes from Mentha microphylla.
PubMed:
Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint.
PubMed:
Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed:
Metabolic fate of S-(-)-pulegone in rat.
PubMed:
Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
PubMed:
The Essential Oil of Poliomintha incana.
PubMed:
Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita).
PubMed:
Microbial transformations of some monoterpenoids and sesquiterpenoids.