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(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate is a citrus-scented ester widely used as a flavor and fragrance agent in food and cosmetic applications.
General Material Description
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate is a chemical ester classified by its molecular formula C13H22O2. It appears as a colorless to pale liquid and possesses a distinctive citrus odor reminiscent of lemon rind, grapefruit, and orange peel. Known under various synonyms including 3,7-nonadien-2-ol, 4,8-dimethyl-, 2-acetate, this compound is recognized for its role in flavor and fragrance applications. The compound’s stereoisomer mixture features both trans and cis forms contributing to its sensory profile. Sourced synthetically for commercial use, it is referenced in the PubChem database under CID 5365819, providing a controlled vocabulary identifier for further chemical data access. Its derivation involves esterification of an unsaturated alcohol with acetic acid, conferring volatility and a fruity aroma desirable in food flavorings and personal care products.
Occurrence, Applicability & Potential Uses
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate occurs primarily as a synthetic ester utilized in flavor and fragrance industries. It provides essential citrus and fruity notes that enhance the sensory qualities of products such as beverages, confectionery, and perfumes. The compound’s inclusion in formulations adheres to regulations including FEMA (US) standards where it is cataloged under FEMA number 4103. Additionally, IFRA (Global) guidelines set usage limits to maintain consumer safety in fragrance applications. Its applicability extends to imparting lemon, grapefruit, and orange characteristics in foods and cosmetics, underscoring its importance in both flavor enhancement and aromatic product development.
Physico-Chemical Properties Summary
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate is characterized by a moderate molecular weight of 210.32 g/mol and an estimated logP of approximately 4.45, indicating substantial lipophilicity. It has a specific gravity ranging between 0.89 and 0.90 at 25 °C, with a refractive index of 1.451 to 1.459 at 20 °C. This compound exhibits boiling points between 276 and 277 °C at standard atmospheric pressure and lower boiling ranges under reduced pressure (75 to 83 °C at 2 mm Hg). Its vapor pressure at 25 °C is very low (around 0.005 mmHg), suggesting low volatility relative to lighter esters. Solubility is confirmed in alcohol and marginally in water (~2.565 mg/L at 25 °C), whereas it is generally insoluble in water alone. These properties influence formulation performance, particularly volatility and solubility in flavor and fragrance matrices.
FAQ
What is (E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate?
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate is a chemical ester known for its citrus-like odor attributes. It is commonly used as a flavor and fragrance ingredient imparting lemon, grapefruit, and orange notes. This compound exists as a mixture of cis and trans isomers and is synthesized for commercial use in various industries.
How is (E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate typically used and where is it found?
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate is mainly employed as a flavoring agent in beverages, confectionery, and other food products, as well as in fragrance formulations for personal care items. It is not naturally abundant but produced synthetically to provide characteristic citrus aromas. Regulatory bodies such as FEMA (US) and IFRA (Global) govern its usage levels to ensure safety and quality in consumer products.
What regulatory standards apply to the use of (E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate?
This compound is subject to safety assessments and guidelines established by organizations including FEMA (US) and IFRA (Global). According to FEMA, it is listed under FEMA number 4103 with defined maximum usage levels in various food categories. IFRA provides recommended concentration limits in fragrances, typically up to 3% in fragrance concentrates. These standards ensure the compound’s safe use in food flavorings and cosmetic formulations without posing health risks.
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 |
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: | FDB009325 |
| ChemSpider: | View |
General Material Information
| Preferred name | (E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate |
| Trivial Name | 3,7-Nonadien-2-ol, 4,8-dimethyl-, 2-acetate |
| Short Description | (+/-)-trans- and cis-4,8-dimethyl-3,7-nonadien-2-yl acetate |
| Formula | C13 H22 O2 |
| CAS Number | 91418-25-6 |
| FEMA Number | 4103 |
| Flavis Number | 9.936 |
| FDA UNII | 7W4J428G2M |
| Nikkaji Number | J3.153.022I |
| xLogP3-AA | 3.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1847 (+/-)-cis and trans-4,8-dimethyl-3,7-nonadien-2-yl acetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 91418-25-6 ; (+/-)-TRANS- AND CIS-4,8-DIMETHYL-3,7-NONADIEN-2-YL ACETATE |
| Synonyms |
|
Suppliers
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 210.31674194336 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.406 to 7.489 |
| Refractive Index | 1.451 to 1.459 @ 20 °C |
| Boiling Point | 276 to 277°C @ 760 mm Hg |
| Boiling Point | 75 to 83°C @ 2 mm Hg |
| Vapor Pressure | 0.005 mmHg @ 25 °C |
| Flash Point TCC Value | 93.89 °C TCC |
| logP (o/w) | 4.452 est |
| Solubility | |
| alcohol | Yes |
| water, 2.565 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Citrus | |
| lemon peel, citrus, earthy, woody | |
| General comment | At 100.00 %. lemon rind citrus earthy woody |
Potential Uses
| Applications | |
| Flavoring purposes | Citrus , Grapefruit , Lemon , Orange |
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 (E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetate usage levels up to: | |||
| 3.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.20 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 19 (μg/person/day) | ||
| Threshold of Concern: | 540 (μg/person/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: 22 | |||
| Click here to view publication 22 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | 2.00000 | 10.00000 | |
| beverages(alcoholic): | 5.00000 | 50.00000 | |
| breakfast cereal: | 5.00000 | 25.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 5.00000 | 20.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | 2.00000 | 10.00000 | |
| gelatins / puddings: | 5.00000 | 20.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 5.00000 | 25.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | 2.00000 | 20.00000 | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 5.00000 | 25.00000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
| 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): | 0.00050 | 0.02500 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.00050 | 0.02500 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.00500 | 0.25000 | |
| Processed fruit (04.1): | 0.00050 | 0.02500 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 0.00050 | 0.02500 | |
| Confectionery (05.0): | 0.05000 | 2.50000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | - | - | |
| Bakery wares (07.0): | 0.00500 | 0.25000 | |
| Meat and meat products, including poultry and game (08.0): | 0.00050 | 0.02500 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.00050 | 0.02500 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.00050 | 0.02500 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.05000 | 2.50000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.05000 | 2.50000 | |
| Ready-to-eat savouries (15.0): | 0.00050 | 0.02500 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.00050 | 0.02500 | |
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): |
| Scientific Opinion on Flavouring Group Evaluation 206 (FGE.206): Consideration of genotoxicity data on representatives for 12 alpha,beta-unsaturated ketones and precursors from chemical subgroup 1.2.3 of FGE.19 by EFSA View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 63, Revision 1 (FGE.63Rev1): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07Rev4 (2012) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 63, Revision 2 (FGE.63Rev2): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07Rev4 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5365819 |
| National Institute of Allergy and Infectious Diseases:Data |
| [(3E)-4,8-dimethylnona-3,7-dien-2-yl] acetate |
| Chemidplus:0091418256 |