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methyl (E)-2-butenoate
Methyl (E)-2-butenoate is an ester known for its green, sharp fruity odor, found naturally in several tropical fruits and used in flavor applications.
General Material Description
Methyl (E)-2-butenoate, also known as methyl E-crotonate or trans-methyl crotonate, is an organic ester with the molecular formula C5H8O2. This colorless liquid exhibits a sharp, green fruity odor, characteristic of some naturally derived esters. It is widely recognized within flavor and fragrance chemistry for its distinctive sensory profile. Structurally classified as a simple α,β-unsaturated ester, methyl (E)-2-butenoate occurs naturally in various edible tropical fruits, including pineapple, lulo fruit, mangaba, and soursop. Due to its natural origins and aromatic attributes, this compound is utilized predominantly as a flavoring agent. Reliable chemical information is accessible through databases such as PubChem. It is generally produced by esterification of (E)-crotonic acid or by extraction from natural sources rich in such esters.
Occurrence, Applicability & Potential Uses
Methyl (E)-2-butenoate is found naturally in a variety of tropical fruits, notably pineapple, lulo fruit, mangaba, and soursop. These occurrences contribute directly to the natural flavor profiles of these fruits. Its primary application is as a flavoring agent, where it imparts a green and sharp fruity note suited for enhancing food products. The compound’s usage is recognized under the FEMA (US) standard for flavoring substances, with established guidelines regulating its concentration levels to ensure sensory effectiveness and safety. Although it once saw use in cosmetic formulations, current standards prohibit methyl (E)-2-butenoate in fragrances due to dermal sensitization concerns indicated by IFRA (Global). Its employment in flavors extends across categories such as dairy products, edible ices, processed fruits, and confectionery, where controlled dosing ensures compliance with regulatory thresholds.
Physico-Chemical Properties Summary
Methyl (E)-2-butenoate is a low molecular weight ester with a molecular weight of approximately 100.12 g/mol and a chemical formula of C5H8O2. It appears as a colorless liquid exhibiting a vapor density higher than air, approximately 3.46 times at standard conditions. The compound’s boiling point ranges from 118 to 120 °C at atmospheric pressure, indicating moderate volatility suitable for flavor release in food formulations. Its specific gravity lies between 0.977 and 0.983 at 25 °C, and it has a refractive index between 1.424 and 1.427 at 20 °C. Methyl (E)-2-butenoate displays slight solubility in water, with estimated values around 1.241 × 104 mg/L at 25 °C, and is readily soluble in alcohol. The flash point is low, at 39 °C, suggesting flammability precautions during handling. An estimated logP of 1.316 indicates moderate lipophilicity, relevant to its distribution in flavors and biological environments. These properties influence formulation decisions, volatility, and application compatibilities.
FAQ
What is methyl (E)-2-butenoate and what are its primary characteristics?
Methyl (E)-2-butenoate is an organic ester commonly known as methyl E-crotonate. It is a colorless liquid with a distinctive sharp, green fruity odor. The compound is characterized by its molecular formula C5H8O2 and moderate volatility, boiling near 118 to 120 °C. It naturally occurs in various tropical fruits and is utilized mainly as a flavoring agent to impart fruity and green notes.
Where does methyl (E)-2-butenoate naturally occur and how is it applied?
This ester is naturally present in fruits such as pineapple, lulo fruit, mangaba, and soursop, contributing to their characteristic aromas. Its principal application is as a flavoring substance in food products. Regulatory frameworks, including FEMA (US), guide safe usage levels. Although previously incorporated in cosmetic products, methyl (E)-2-butenoate is no longer used for fragrance purposes due to allergens concerns identified by IFRA (Global). Its controlled use across food categories enhances fruit- and green-related flavor profiles.
What are the regulatory considerations and safety aspects for methyl (E)-2-butenoate?
Methyl (E)-2-butenoate is evaluated under multiple safety standards such as FEMA (US) for flavorings and IFRA (Global) for fragrance usage. While permitted as a flavoring agent within specific concentration limits, it is prohibited in perfumes owing to dermal sensitization risks. Its hazard classification indicates irritancy and high flammability, requiring standard precautionary measures during handling and formulation. Toxicological data show relatively low acute toxicity levels, but exposure controls and adherence to established thresholds ensure consumer safety.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| methyl (E)-but-2-enoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 623-43-8 |
| Pubchem (cid): | 638132 |
| Pubchem (sid): | 134977110 |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2916.19.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | methyl (E)-2-butenoate |
| Trivial Name | Methyl E-crotonate |
| Short Description | trans-methyl crotonate |
| Formula | C5 H8 O2 |
| CAS Number | 623-43-8 |
| Flavis Number | 9.636 |
| ECHA Number | 210-793-7 |
| FDA UNII | 3T02JIH93S |
| Nikkaji Number | J43.555D |
| Beilstein Number | 1720292 |
| MDL | MFCD00009287 |
| xLogP3-AA | 0.90 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 100.11715698242 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.13 to 8.18 |
| Refractive Index | 1.424 to 1.427 @ 20 °C |
| Boiling Point | 118 to 120°C @ 760 mm Hg |
| Vapor Pressure | 14.869 mmHg @ 25 °C |
| Vapor Density | 3.46 |
| Flash Point TCC Value | 3.89 °C TCC |
| logP (o/w) | 1.316 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 1.241e+004 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| sharp, green, fruity | |
| General comment | At 1.00 % in dipropylene glycol. sharp green fruity |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 11 - Highly flammable. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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 36/37/39 - Wear suitable clothing, 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 > 3200 mg/kg (MFRM, 1979) oral-mouse LD50 1600 mg/kg (MFRM, 1979) oral-mouse LD50 1600 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 865, 1979. oral-rat LD50 > 3200 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 865, 1979. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 865, 1979. skin-guinea pig LD50 10 ml/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 865, 1979. | |
| Inhalation Toxicity: | |
| inhalation-rat LC > 19000 ppm/6H Food and Cosmetics Toxicology. Vol. 17, Pg. 865, 1979. | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| IFRA Critical Effect: | |||
| Dermal sensitization | |||
| View the IFRA Standard | |||
| Recommendation for methyl (E)-2-butenoate usage levels up to: | |||
| PROHIBITED: Should not be used as a fragrance ingredient. | |||
| 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: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| 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): |
| Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to Flavouring Group Evaluation 5: Esters of 23 branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and 24 branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 View page or View pdf |
| Flavouring Group Evaluation 5, Revision 1 (FGE.05Rev1):Esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 62 (FGE.62) Consideration of linear and branched-chain aliphatic unsaturated, unconjugated alcohols, aldehydes, acids, and related esters evaluated by JECFA (61st meeting) structurally related to esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids evaluated by EFSA in FGE.05 (2005) and to straight- and branched-chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters evaluated by EFSA in FGE.06 (2004) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 71: Consideration of aliphatic, linear, alpha,beta-unsaturated carboxylic acids and related esters View page or View pdf |
| Flavouring Group Evaluation 72 (FGE.72): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids. Esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010) View page or View pdf |
| Flavouring Group Evaluation 5, Revision 2 (FGE.05Rev2): Branched- and straight-chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols from chemical groups 1, 2, 3 and 5 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 95 (FGE.95): Consideration of aliphatic, linear or branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (69th meeting) structurally related to esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids evaluated by EFSA in FGE.05Rev1 (2008) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):623-43-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :638132 |
| National Institute of Allergy and Infectious Diseases:Data |
| SCCNFP:opinion |
| WISER:UN 3272 |
| WGK Germany:2 |
| methyl (E)-but-2-enoate |
| Chemidplus:0000623438 |
| RTECS:GQ5710000 for cas# 623-43-8 |