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2-ethyl hexyl acetate
2-ethyl hexyl acetate is an organic ester used mainly as a flavor and fragrance agent noted for its earthy and woody aromatic properties.
General Material Description
2-ethyl hexyl acetate is an organic ester with the molecular formula C10H20O2, known chemically as the acetate ester of 2-ethyl-1-hexanol. It appears as a clear, colorless liquid with a characteristic earthy and woody odor profile. In sensory domains, it imparts notes resembling cypress, pine, fern, and subtle herbaceous undertones, making it valuable in fragrance compositions. Synonyms include acetic acid 2-ethylhexyl ester and 2-ethyl-1-hexyl acetate among others. As a compound, it is listed under a controlled vocabulary in ChEBI. Industrially, it is synthesized typically by esterification of 2-ethyl-1-hexanol and acetic acid and is recovered for use primarily in flavor and fragrance applications.
Occurrence, Applicability & Potential Uses
This ester naturally occurs in trace amounts in some dairy products, including milk, contributing to subtle flavor aspects. It is widely applied in the flavor and fragrance industries as a component that adds earthy, woody, and herbal notes to perfumes and flavor formulations. 2-ethyl hexyl acetate functions as a solvent and is used as a substitute for natural materials such as cypress oil and fir needle oil. Its presence enhances fragrance blends including oriental, patchouli, vetiver, and galbanum accords. The chemical sees use as a flavoring agent, where its pine and green pea-like aspects are beneficial. Regulatory standards including FEMA (US) integrate limits for its use in food flavors, reflecting its acceptance and safety profile in controlled amounts.
Physico-Chemical Properties Summary
2-ethyl hexyl acetate is a clear, colorless liquid with a boiling point between 196 and 199°C at atmospheric pressure, indicating moderate volatility suitable for fragrance evaporation and flavor release. Its specific gravity ranges from 0.87 to 0.876 at 25°C, and its refractive index varies approximately from 1.417 to 1.423 at 20°C. The compound exhibits a relatively low vapor pressure of 0.413 mmHg at 25°C, reflecting moderate volatility. Its estimated logP value around 3.686 signifies lipophilic character, supporting its solvent properties and affinity for oily phases in formulations. The flash point near 71°C (160°F) calls for measured handling precautions. It is soluble in alcohol and has low water solubility (approximately 38.59 mg/L at 25°C). These attributes influence its efficacy and handling in flavors, fragrances, and solvents.
FAQ
What is 2-ethyl hexyl acetate and how is it characterized?
2-ethyl hexyl acetate is an organic ester derived from 2-ethyl-1-hexanol and acetic acid. It is a clear, colorless liquid with a distinctive earthy and woody odor, used primarily in flavor and fragrance applications. Chemically, it is identified by the formula C10H20O2 and has synonyms such as acetic acid 2-ethylhexyl ester. Industrially sourced via esterification, it contributes aromatic notes reminiscent of pine, fern, and herbal impressions.
Where does 2-ethyl hexyl acetate occur naturally and how is it used?
This compound is found in trace quantities in natural products like milk, influencing subtle flavor components. Its applications span flavoring, where it enhances pea and pine notes, and fragrance, where it serves as a component imparting woody, earthy, and herbaceous aromas. Additionally, it acts as a solvent and can replace natural substances such as cypress and fir needle oils in perfumery. Usage levels are defined by industry and regulatory bodies to ensure product safety.
What safety and regulatory standards govern the use of 2-ethyl hexyl acetate?
2-ethyl hexyl acetate is regulated for use in flavors and fragrances under guidelines such as FEMA (US) and IFRA (Global). Its safety has been assessed with data indicating it is an irritant to eyes, respiratory system, and skin but without classification as hazardous under OSHA HCS standards. Usage limits in fragrances may reach up to 4% in concentrate, and maximum daily intake limits have been established. Safety datasheets and fragrance material safety evaluations provide guidance for proper use and exposure control.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2-ethylhexyl acetate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 103-09-3 |
| Pubchem (cid): | 7635 |
| Pubchem (sid): | 134971906 |
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 |
| CHEBI: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2915.39.9000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Formulations/Preparations: grade: technical (about 95%). | |
General Material Information
| Preferred name | 2-ethyl hexyl acetate |
| Trivial Name | 2-Ethylhexyl acetate |
| Short Description | acetic acid, 2-ethylhexyl ester |
| Formula | C10 H20 O2 |
| CAS Number | 103-09-3 |
| Deleted CAS Number | 12261-98-2 |
| Flavis Number | 9.381 |
| ECHA Number | 203-079-1 |
| FDA UNII | 2C7K8OA8SB |
| Nikkaji Number | J46.181D |
| Beilstein Number | 1758321 |
| MDL | MFCD00027249 |
| xLogP3-AA | 3.20 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 172.26780700684 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.239 to 7.289 |
| Refractive Index | 1.417 to 1.423 @ 20 °C |
| Boiling Point | 196 to 199°C @ 760 mm Hg |
| Vapor Pressure | 0.413 mmHg @ 25 °C |
| Flash Point TCC Value | 71.11 °C TCC |
| logP (o/w) | 3.686 est |
| Solubility | |
| alcohol | Yes |
| water, 38.59 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Earthy | |
| earthy, herbal, humus, dirty | |
| General comment | At 10.00 % in dipropylene glycol. earthy herbal humus undergrowth |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Cypress oil replacer , Earth , Fennel , Fern , Fir needle oil replacer , Fungus , Galbanum , Oriental , Patchouli , Pine scotch pine , Root , Rose geranium , Vetiver , Woody |
| Flavoring purposes | Pea green pea , Pine scotch pine |
| Other purposes | Solvents , Truffle |
| Cosmetic purposes | Perfuming agents , Solvents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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 3000 mg/kg (Smyth & Carpenter, 1944) oral-mouse LD50 > 3200 mg/kg Kodak Company Reports. Vol. 21May1971 oral-rat LD50 3000 mg/kg Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. | |
| Dermal Toxicity: | |
| skin-guinea pig LD50 > 20 ml/kg Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. skin-rabbit LD50 > 20 ml/kg Union Carbide Data Sheet. Vol. 4/21/1967 | |
| Inhalation Toxicity: | |
| inhalation-rat LC50 > 1100 ppm/6H Kodak Company Reports. Vol. 21MAY1971 | |
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 2-ethyl hexyl acetate usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.12 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3900 (μg/person/day) | ||
| Threshold of Concern: | 540 (μg/person/day) | ||
| Structure Class: | II | ||
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 7.00000 | 35.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 5.00000 | 25.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 10.00000 | 50.00000 | |
| Processed fruit (04.1): | 7.00000 | 35.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 10.00000 | 50.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 5.00000 | 25.00000 | |
| Bakery wares (07.0): | 10.00000 | 50.00000 | |
| Meat and meat products, including poultry and game (08.0): | 2.00000 | 10.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 10.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 25.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 10.00000 | 50.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 5.00000 | 25.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 10.00000 | 50.00000 | |
| Ready-to-eat savouries (15.0): | 20.00000 | 100.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 5.00000 | 25.00000 | |
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 04 - 2-Ethylhexyl derivatives from chemical group 2 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):103-09-3 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7635 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| 2-ethylhexyl acetate |
| Chemidplus:0000103093 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:AH5600000 for cas# 103-09-3 |