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(±)-1,2,5,6-tetrahydrocuminic acid
(±)-1,2,5,6-tetrahydrocuminic acid is a cyclohexene carboxylic acid used as a flavor and fragrance agent with a spicy, animalic sensory profile.
General Material Description
(±)-1,2,5,6-tetrahydrocuminic acid belongs to the chemical class of cyclohexene carboxylic acids characterized by the molecular formula C10H16O2. This compound typically appears as a colorless to pale liquid or solid, with a distinctive spicy and slightly animalic odor profile reminiscent of cumin. It is known also under several synonyms such as 4-(1-methylethyl)-3-cyclohexene-1-carboxylic acid and 4-isopropyl-3-cyclohexene-1-carboxylic acid. The compound is available commercially and can be synthetically derived for use in flavor and fragrance applications. A controlled vocabulary reference for this compound can be found in PubChem CID 62117. Its sensory and chemical traits make it relevant in creating complex aroma profiles.
Occurrence, Applicability & Potential Uses
(±)-1,2,5,6-tetrahydrocuminic acid occurs primarily as a synthetic flavor and fragrance ingredient. It imparts spicy, animalic, and mildly sweaty notes and is found in perfuming agents and flavor formulations to replicate or replace natural cumin and costus aromas. The compound's flavoring applications align with FEMA (US) regulation number 3731, under which it is recognized and evaluated for safe use levels. It serves as a cost-effective substitute for natural cumin oil in various food and cosmetic products, enhancing sensory complexity without the biological variability of natural extracts.
Physico-Chemical Properties Summary
(±)-1,2,5,6-tetrahydrocuminic acid exhibits physicochemical properties important for fragrance and flavor formulation. It has a molecular weight of approximately 168.24 g/mol and a moderate estimated logP of 2.586, indicating moderate lipophilicity and compatibility with organic solvents. The compound boils between 275 and 276°C at standard atmospheric pressure, suggesting stability under common thermal processing. It shows low vapor pressure at 25°C (0.001 mmHg), reflecting low volatility beneficial for sustained aroma release. Solubility tests indicate slight solubility in water (approximately 131.8 mg/L at 25°C) and good solubility in alcohols, which aids formulation versatility. The flash point is around 130°C (267°F), indicating a relatively safe handling profile in manufacturing environments.
FAQ
What is (±)-1,2,5,6-tetrahydrocuminic acid and what are its synonyms?
(±)-1,2,5,6-tetrahydrocuminic acid is a cyclohexene carboxylic acid compound used primarily as a flavor and fragrance ingredient. It has several synonyms including 4-(1-methylethyl)-3-cyclohexene-1-carboxylic acid and 4-isopropyl-3-cyclohexene-1-carboxylic acid. Its molecular formula is C10H16O2, and it is recognized under various chemical identifiers such as CAS number 71298-42-5 and FEMA number 3731.
Where is (±)-1,2,5,6-tetrahydrocuminic acid commonly used and what are its sensory characteristics?
(±)-1,2,5,6-tetrahydrocuminic acid is primarily used in flavor and fragrance formulations. It imparts a spicy, animalic scent with nuances reminiscent of cumin and costus. These sensory characteristics make it suitable as a flavoring agent and a perfume ingredient, often used to replace or augment natural cumin oil. Its physicochemical properties support its incorporation in various product matrices including baked goods, seasonings, and personal care products.
How is (±)-1,2,5,6-tetrahydrocuminic acid regulated and sourced for commercial use?
(±)-1,2,5,6-tetrahydrocuminic acid is recognized by FEMA (US) under the number 3731 and by JECFA with the group number 976 for food flavoring use. It is generally synthetically produced for commercial applications. Regulatory assessments indicate no significant hazards under OSHA HCS classifications, with negligible toxicity observed in studies. Usage levels in foods and fragrances conform to standards governed by IFRA (Global) and other international regulatory bodies, ensuring consumer safety in permitted concentrations.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 4-propan-2-ylcyclohex-3-ene-1-carboxylic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 71298-42-5 |
| Pubchem (cid): | 62117 |
| Pubchem (sid): | 135019542 |
| Publications by US Patents | |
| 4,606,925 - Flavoring with alkyl-substituted cyclohexyl and cyclohexenyl carboxylic acids | |
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): | Search |
| FooDB: | FDB016171 |
| ChemSpider: | View |
General Material Information
| Preferred name | (±)-1,2,5,6-tetrahydrocuminic acid |
| Trivial Name | 4-(1-Methylethyl)-3-cyclohexene-1-carboxylic acid |
| Short Description | 3-cyclohexene-1-carboxylic acid, 4-isopropyl- |
| Formula | C10 H16 O2 |
| CAS Number | 71298-42-5 |
| Deleted CAS Number | 56424-87-4 |
| FEMA Number | 3731 |
| Flavis Number | 8.067 |
| FDA UNII | JP3KX91NB0 |
| Nikkaji Number | J1.539.910D |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 976 1,2,5,6-tetrahydrocuminic acid |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 56424-87-4 ; 1,2,5,6-TETRAHYDROCUMINIC ACID |
| Synonyms |
|
Suppliers
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.2359161377 |
| Boiling Point | 275 to 276°C @ 760 mm Hg |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 130.56 °C TCC |
| logP (o/w) | 2.586 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 131.8 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| animal, cumin, sweaty | |
| General comment | At 100.00 %. animalic cumin sweaty |
Potential Uses
| Applications | |
| Odor purposes | Costus , Cumin oil replacer |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| 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: | |
| gavage-rat LD50 > 2500 mg/kg Study inadequate for derivation of LD50. Also only code name given for substance. (Levenstein, 1981a) | |
| Dermal Toxicity: | |
| Not determined | |
| 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 | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | ND (μg/capita/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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.50000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | 1.00000 | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 5.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | 2.50000 | |
| fats / oils: | - | - | |
| fish products: | - | 5.00000 | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 5.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | 0.50000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 5.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | 5.00000 | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | 200.00000 | |
| snack foods: | - | 5.00000 | |
| soft candy: | - | - | |
| soups: | - | 2.50000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
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): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 12 (FGE.12); Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 - Flavouring Group Evaluation 12, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 73, (FGE.73)[1] - Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde and esters evaluated by EFSA in FGE.12 (2005) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 1 (FGE.73Rev1): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters evaluated by EFSA in FGE.12Rev2 (2011) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 2 (FGE.73Rev2): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev3 (2012) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 3 (FGE.73Rev3): Consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev4 (2013) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 4 (FGE.73Rev4): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev5 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 5 (FGE.73Rev5): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th, 63rd and 86th meeting) and structurally related to substances evaluated in FGE.12Rev5 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):71298-42-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :62117 |
| National Institute of Allergy and Infectious Diseases:Data |
| 4-propan-2-ylcyclohex-3-ene-1-carboxylic acid |
| Chemidplus:0071298425 |