| Name: | but-2-enoic acid |
| CAS Number: | 3724-65-0 |  3D/inchi
|
| Other(deleted CASRN): | 15105-17-6 |
| ECHA EINECS - REACH Pre-Reg: | 223-077-4 |
| FDA UNII: | Search |
| Beilstein Number: | 1098434 |
| CoE Number: | 10080 |
| XlogP3: | 0.70 (est) |
| Molecular Weight: | 86.09022000 |
| Formula: | C4 H6 O2 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
| EFSA/JECFA Comments: |
| Composition of mixture to be specified.
Composition of stereoisomeric mixture to be specifed. EU Union List chemical name to be changed to (E,Z)-But-2-enoic acid |
Category: flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | white solid (est) |
| Assay: | 99.00 to 100.00 sum of isomers
|
| Food Chemicals Codex Listed: | No |
| Melting Point: | 70.00 to 73.00 °C. @ 760.00 mm Hg
|
| Boiling Point: | 185.00 °C. @ 760.00 mm Hg
|
| Boiling Point: | 66.00 to 67.00 °C. @ 10.00 mm Hg
|
| Vapor Pressure: | 0.505000 mmHg @ 25.00 °C. (est) |
| Vapor Density: | 2.9 ( Air = 1 ) |
| Flash Point: | 186.00 °F. TCC ( 85.56 °C. )
|
| logP (o/w): | 0.720 |
| Soluble in: |
| | alcohol | | | water, 8.60E+04 mg/L @ 25 °C (exp) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor Type: milky |
| roasted burnt |
| Odor Description:at 0.10 % in propylene glycol. roasted burnt |
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| European information : |
| Most important hazard(s): | | Xn - Harmful. |
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R 34 - Causes burns.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 27 - Take off immediately all contaminated clothing.
S 28 - After contact with skin, wash immediately with plenty of water.
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 1000 mg/kg
Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.
oral-mouse LD50 4800 mg/kg
Biochemical Journal. Vol. 34, Pg. 1196, 1940.
intraperitoneal-mouse LD50 25 mg/kg
"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
|
| Dermal Toxicity: |
skin-rabbit LD50 600 mg/kg
"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 309, 1986.
subcutaneous-mouse LD50 3590 mg/kg
Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
skin-guinea pig LD50 200 mg/kg
"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | | flavoring agents |
| Recommendation for 2-butenoic acid usage levels up to: | | | not for fragrance use.
|
| |
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 4.00 (μg/capita/day) |
| Threshold of Concern: | 1800 (μg/person/day) |
| Structure Class: | I |
| 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: | 5.00000 | 7.00000 |
| beverages(nonalcoholic): | 2.00000 | 5.00000 |
| beverages(alcoholic): | - | - |
| breakfast cereal: | - | - |
| cheese: | - | - |
| chewing gum: | - | - |
| condiments / relishes: | - | - |
| confectionery froastings: | - | - |
| egg products: | - | - |
| fats / oils: | 0.20000 | 0.50000 |
| fish products: | - | - |
| frozen dairy: | 5.00000 | 7.00000 |
| fruit ices: | - | - |
| gelatins / puddings: | 5.00000 | 7.00000 |
| 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: | 5.00000 | 7.00000 |
| 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 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 14, Revision 1 (FGE.14Rev1): Phenethyl alcohol, aldehyde, acetals, carboxylic acid and related esters from chemical group 15 and 22 [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
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Flavouring Group Evaluation 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 71: Consideration of aliphatic, linear, alpha,beta-unsaturated carboxylic acids and related esters
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 13Rev1: Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
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 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 5, Revision 3 (FGE.05Rev3): Branched- and straight-chain unsaturated aldehydes, dienals, unsaturated and saturated carboxylic acids and related esters with saturated and unsaturated aliphatic alcohols and a phenylacetic acid related ester from chemical groups 1, 2, 3, 5 and 15
View page or View pdf
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| EPI System: View |
| NIOSH International Chemical Safety Cards:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):3724-65-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :19499 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2823 |
| WGK Germany:1 |
| but-2-enoic acid |
| Chemidplus:0003724650 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:3724-65-0 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | but-2-enoic acid | | 2- | butenic acid | | 2- | butenoic acid | | a- | butenoic acid | | alpha- | butenoic acid | | 2- | butenoic acid (crotonic acid) | | | crotonic acid | | a- | crotonic acid | | alpha- | crotonic acid | | b- | methacrylic acid | | beta- | methacrylic acid | | 3- | methyl acrylic acid | | beta- | methyl acrylic acid | | 3- | methylacrylic acid | | b- | methylacrylic acid | | beta- | methylacrylic acid |
Articles:
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| PubMed:Preclinical evaluation of 4-[3,5-bis(2-chlorobenzylidene)-4-oxo-piperidine-1-yl]-4-oxo-2-butenoic acid, in a mouse model of lung cancer xenograft. |
| PubMed:Synthesis of unsaturated α-acyloxybenzothiazoleamides via the Passerini three-component reaction. |
| PubMed:Automated thermochemolysis reactor for detection of Bacillus anthracis endospores by gas chromatography-mass spectrometry. |
| PubMed:(E)-4-aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: design, antiproliferative activity and inhibition of tubulin polymerization. |
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| PubMed:Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR. |
| PubMed:Cyclodextrin-mediated entrapment of curcuminoid 4-[3,5-bis(2-chlorobenzylidene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] or CLEFMA in liposomes for treatment of xenograft lung tumor in rats. |
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| PubMed:Inhibition of homodimerization of toll-like receptor 4 by 4-oxo-4-(2-oxo-oxazolidin-3-yl)-but-2-enoic acid ethyl ester. |
| PubMed:GABAergic actions on cholinergic laterodorsal tegmental neurons: implications for control of behavioral state. |
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| PubMed:Suppression of Toll-like receptor 2 or 4 agonist-induced cyclooxygenase-2 expression by 4-oxo-4-(2-oxo-oxazolidin-3-yl)-but-2-enoic acid ethyl ester. |
| PubMed:Effects of Fusarium mycotoxin butenolide on myocardial mitochondria in vitro. |
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| PubMed:Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon. |
| PubMed:(Z)-Methyl 3-(4-ethoxy-anilino)but-2-enoate. |
| PubMed:Formal synthesis of the ACE inhibitor benazepril x HCl via an asymmetric aza-Michael reaction. |
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| PubMed:[GC-MS analysis of the fatty components of pollen Typhae before and after being carbonized]. |
| PubMed:Depletion of intracellular glutathione mediates butenolide-induced cytotoxicity in HepG2 cells. |
| PubMed:Hematological and clinical chemistry changes induced by subchronic dosing of a novel phosphorothionate (RPR-V) in Wistar male and female rats. |
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| PubMed:[Isolation and structure identification of chemical constituents from Anabasis brevifolia]. |
| PubMed:Effects of a novel organophosphorus pesticide (RPR-V) on extra hepatic detoxifying enzymes after repeated oral doses in rats. |
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