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dihydrocarvyl acetate
Dihydrocarvyl acetate is a floral and minty flavor and fragrance compound derived from natural plant sources, with CAS number 20777-49-5.
General Material Description
Dihydrocarvyl acetate is an organic ester compound with the molecular formula C12H20O2. It appears as a colorless to pale yellow liquid exhibiting a floral and medium-strength odor profile with minty and sweet nuances. Known also by synonyms such as L-p-menth-8(9)-en-2-yl acetate and carhydrine (IFF), this compound is commonly derived from or identified in essential oils of plants like spearmint and caraway. It functions as a flavor and fragrance agent notable for its floral, green, and fruity aroma characteristics. This material is indexed in chemical databases such as PubChem and plays a role in both synthetic flavorings and perfuming applications.
Occurrence, Applicability & Potential Uses
Dihydrocarvyl acetate naturally occurs in several plant sources including anise, caraway, celery, and spearmint plants, as well as in spearmint oils with concentrations ranging approximately 0.35–0.43%. Due to its sensory profile exhibiting floral, minty, and seedy notes, it is utilized extensively as a flavoring agent in tropical and fruity food products. Additionally, its fragrance attributes contribute to its application in perfuming agents for cosmetics and personal care items. Regulatory assessments such as the FEMA (US) GRAS classification support its use within monitored usage limits in various consumables and fragrances, adhering to safety guidelines under IFRA (Global) standards.
Physico-Chemical Properties Summary
This compound has a molecular weight of approximately 196.29 g/mol and a moderate estimated logP of 3.724, indicating appreciable lipophilicity relevant to formulation stability and volatility. It exhibits a boiling point range between 232 and 234°C at atmospheric pressure, with a relatively low vapor pressure of 0.057 mmHg at 25°C, contributing to its substantive aroma profile. The specific gravity ranges from about 0.941 to 0.949 at 25°C, marking it denser than water with slight solubility demonstrated. Dihydrocarvyl acetate is soluble in alcohol and slightly soluble in water, aligning with its ester chemical nature. Its flash point is measured near 90°C (194°F), reflective of moderate flammability under specific conditions.
FAQ
What is dihydrocarvyl acetate and where is it found naturally?
Dihydrocarvyl acetate is an organic ester used primarily in flavor and fragrance applications. It occurs naturally in plants such as anise, caraway, celery, horsemint, and spearmint, often contributing to their characteristic aromas. It is identified notably in spearmint oils and caraway seed extracts, where it plays a role in the floral, minty, and green notes typical to these botanicals.
How is dihydrocarvyl acetate used in commercial products?
The compound is employed as a flavoring agent in food and beverage products to impart tropical and floral characteristics, especially in formulations aiming for mint and berry notes. Additionally, its scent profile makes it suitable as a perfuming ingredient in cosmetic and personal care products. Usage levels are regulated to ensure safety and consistency in finished goods, with recognized standards guiding its application.
What regulations govern the use of dihydrocarvyl acetate and how is its safety assessed?
Dihydrocarvyl acetate is recognized by FEMA (US) as generally safe for use in flavorings within specified concentration limits. It is also assessed under IFRA (Global) guidelines for fragrance usage levels to prevent adverse effects. Toxicological data indicate low acute toxicity, and safety assessments have found no significant irritation or sensitization at relevant exposure levels, supporting its controlled application in consumer products.
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
| (2-methyl-5-prop-1-en-2-ylcyclohexyl) acetate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 20777-49-5 |
| Pubchem (cid): | 30248 |
| Pubchem (sid): | 135046103 |
| Flavornet: | 20777-49-5 |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB41469 |
| FooDB: | FDB021427 |
| Export Tariff Code: | 2915.39.9050 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | dihydrocarvyl acetate |
| Trivial Name | (±)-Dihydrocarvyl acetate |
| Short Description | L-p-menth-8(9)-en-2-yl acetate |
| Formula | C12 H20 O2 |
| CAS Number | 20777-49-5 |
| FEMA Number | 2380 |
| Flavis Number | 9.216 |
| ECHA Number | 244-029-9 |
| FDA UNII | XC721O44HW |
| Nikkaji Number | J160.107E |
| Beilstein Number | 2443836 |
| MDL | MFCD00001501 |
| COE Number | 10859 |
| xLogP3-AA | 3.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 379 dihydrocarvyl acetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 20777-49-5 ; DIHYDROCARVYL ACETATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 196.28979492188 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.83 to 7.897 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.848 to 7.914 |
| Refractive Index | 1.458 to 1.463 @ 20 °C |
| Boiling Point | 232 to 234°C @ 760 mm Hg |
| Vapor Pressure | 0.057 mmHg @ 25 °C |
| Flash Point TCC Value | 90 °C TCC |
| logP (o/w) | 3.724 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 8.307 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Floral | |
| floral, rose, cumin, sweet, minty, green, fruity, vegetable, camphoreous, pine, beany | |
| Odor strength | medium |
| Substantivity | 32 hour(s) at 100.00 % |
| Luebke, William tgsc, (1989) | At 100.00 %. floral rose cuminseed sweet minty |
| Mosciano, Gerard P&F 21, No. 6, 49, (1996) | Floral, green, fruity, vegetative, camphoreous and piney with bean nuances |
| Flavor Type: Floral | |
| floral, vegetable, minty, cooling, rose, beany | |
| Mosciano, Gerard P&F 21, No. 6, 49, (1996) | At 25.00 ppm. Floral, vegetative and minty with cooling, rose and bean nuances |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Berry , Mint , Spearmint , Tuberose |
| Flavoring purposes | Tropical |
| Other purposes | Seedy |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. | |
| 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. | |
| Human Experience: | |
| 4 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 > 5000 mg/kg (Moreno, 1980f) oral-rat LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 21, Pg. 843, 1983. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 21, Pg. 843, 1983. | |
| 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 dihydrocarvyl acetate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 9.70 (μg/capita/day) | ||
| 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 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 22.00000 | |
| beverages(nonalcoholic): | 2.00000 | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 10.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 20.00000 | |
| fruit ices: | - | 20.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 22.00000 | |
| 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: | - | - | |
| 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 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25 View page or View pdf |
| Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):20777-49-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :30248 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| (2-methyl-5-prop-1-en-2-ylcyclohexyl) acetate |
| Chemidplus:0020777495 |
| RTECS:OT0210000 for cas# 20777-49-5 |