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4-isopropyl-2-cyclohexenone
4-isopropyl-2-cyclohexenone is a flavor and fragrance compound known for its spicy, cumin-like aroma used in essential oils and food flavorings.
General Material Description
4-isopropyl-2-cyclohexenone, commonly known as (±)-Cryptone, is a cyclic ketone with the molecular formula C9H14O. It appears as a clear liquid and exhibits a distinctive spicy aroma characterized by cumin, caraway, woody, and herbal notes. This compound is a member of the alicyclic ketones chemical family and is often utilized in flavor and fragrance applications. It features in essential oils derived from various botanicals such as cumin seed, eucalyptus, and lavender. As detailed in the PubChem database, 4-isopropyl-2-cyclohexenone is structurally defined as 4-(1-methylethyl)-2-cyclohexen-1-one. Its presence in natural sources and ability to impart warm, spicy olfactory impressions make it of interest for both flavorists and perfumers.
Occurrence, Applicability & Potential Uses
4-isopropyl-2-cyclohexenone naturally occurs in diverse plant-derived oils including cumin seed, various species of eucalyptus leaf and fruit oils, lavender, peppermint, and parsley leaf. Its distribution spans several aromatic herbs and spices where it contributes to the complex scent profiles. The compound is widely applied as a flavor and fragrance agent to impart spicy, herbal, woody, lavender, mint, and peppery notes. Regulatory evaluation under FEMA (US) identifies it by the number 3939, confirming its recognized use in flavor formulations. Additionally, IFRA (Global) guidelines recommend usage limits, typically up to 1.0% concentration in fragrance concentrates, aligning with safety assessments for consumer products.
Physico-Chemical Properties Summary
4-isopropyl-2-cyclohexenone is a moderately lipophilic molecule, with an estimated logP of 1.589 indicating affinity for organic phases. At 25 °C its specific gravity ranges from 0.93 to 0.95, and its refractive index falls between 1.481 and 1.49 measured at 20 °C. The compound exhibits low vapor pressure (0.213 mmHg at 25 °C), reflecting moderate volatility relevant to evaporation and scent release. Solubility characteristics include good solubility in alcohol and limited but measurable solubility in water. The flash point is approximately 87 °C (189 °F, tag closed cup), indicating moderate flammability under ambient conditions. These properties influence formulation decisions in flavor and fragrance systems requiring balancing volatility, stability, and miscibility.
FAQ
What is 4-isopropyl-2-cyclohexenone and what are its key characteristics?
4-isopropyl-2-cyclohexenone, also called (±)-Cryptone, is a cyclic ketone compound with formula C9H14O. It is recognized for its spicy, cumin-like aroma and is commonly found in essential oils such as cumin, eucalyptus, and lavender. The compound is a clear liquid with moderate volatility and solubility in alcohol. It serves mainly as a flavor and fragrance ingredient in various consumer products.
Where does 4-isopropyl-2-cyclohexenone occur naturally and how is it used?
This compound occurs naturally in multiple plant oils, including cumin seed, eucalyptus leaf and fruit oils from several species, lavender, peppermint, and parsley leaf. It is used primarily as a flavoring and fragrance agent to convey spicy, herbal, woody, lavender, mint, and pepper notes in formulations. Its sensory profile makes it valuable for perfumery and flavor applications requiring warm and complex odor nuances.
What regulations and safety evaluations apply to 4-isopropyl-2-cyclohexenone in flavor and fragrance use?
4-isopropyl-2-cyclohexenone is listed under FEMA (US) as substance number 3939 and has been assessed for safety in flavor applications, including usage limits generally up to 1.0% in fragrance concentrates per the IFRA (Global) code of practice. Safety assessments have not identified specific hazard classifications by OSHA (US), and it is recognized by the FEMA Expert Panel as generally safe when used within recommended limits. Extensive evaluations by EFSA (EU) and other authorities provide supporting toxicological data accessible through public databases.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
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: | FDB014728 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 4-isopropyl-2-cyclohexenone |
| Trivial Name | (±)-Cryptone |
| Short Description | 4-propan-2-ylcyclohex-2-en-1-one |
| Formula | C9 H14 O |
| CAS Number | 500-02-7 |
| Deleted CAS Number | 21293-23-2 |
| FEMA Number | 3939 |
| Flavis Number | 7.172 |
| ECHA Number | 207-898-5 |
| FDA UNII | 0U8E4W4GBB |
| Nikkaji Number | J11.669F |
| COE Number | 11127 |
| xLogP3-AA | 2.00 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1110 4-isopropyl-2-cyclohexenone |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 500-02-7 ; ISOPROPYL-2-CYCLOHEXENONE |
| Synonyms |
|
Suppliers
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.20977783203 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.739 to 7.905 |
| Refractive Index | 1.481 to 1.49 @ 20 °C |
| Vapor Pressure | 0.213 mmHg @ 25 °C |
| Flash Point TCC Value | 87.22 °C TCC |
| logP (o/w) | 1.589 est |
| Solubility | |
| alcohol | Yes |
| water, 593.4 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| spicy, cumin, caraway, woody, herbal | |
| General comment | At 100.00 %. spice cumin caraway woody herbal |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Costus , Herbal , Lavender , Mint , Pepper , Spice , Woody |
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: | |
| Not determined | |
| 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 | |||
| Recommendation for 4-isopropyl-2-cyclohexenone usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.0012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.001 (μg/capita/day) | ||
| Structure Class: | II | ||
| 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: 19 | |||
| Click here to view publication 19 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.15000 | 0.30000 | |
| beverages(nonalcoholic): | 0.05000 | 0.10000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.05000 | 0.10000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 0.05000 | 0.10000 | |
| 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: | 0.10000 | 0.20000 | |
| soups: | - | - | |
| 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): |
| Flavouring Group Evaluation 212: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 212 Revision 1 (FGE.212Rev1): alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19. View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 51, Revision 1 (FGE.51Rev1): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by the JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev3 (2011) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 212 Revision 3 (FGE.212Rev3): a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19 View page or View pdf |
| Flavouring Group Evaluation 51, Revision 2 (FGE.51Rev2): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev6 (2015) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):500-02-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :92780 |
| National Institute of Allergy and Infectious Diseases:Data |
| 4-propan-2-ylcyclohex-2-en-1-one |
| Chemidplus:0000500027 |