EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

2-butenoic acid
crotonic acid

Supplier Sponsors

Name:but-2-enoic acid
CAS Number: 3724-65-0Picture of molecule3D/inchi
Other:15105-17-6
ECHA EINECS - REACH Pre-Reg:223-077-4
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 or firefox)
EFSA/JECFA Comments:
Composition of mixture to be specified.
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
FLAVIS Number:08.072 (Old)
DG SANTE Food Flavourings:08.072 but-2-enoic acid
DG SANTE Food Contact Materials:but-2-enoic acid
FEMA Number:3908 2-butenoic acid
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):3724-65-0 ; (E)-2-BUTENOIC ACID
FDA Regulation:
FDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS
Subpart B--Substances for Use Only as Components of Adhesives
Sec. 175.105 Adhesives.


FDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS
Subpart C--Substances for Use as Components of Coatings
Sec. 175.350 Vinyl acetate/crotonic acid copolymer.


FDA PART 176 -- INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS
Subpart B--Substances for Use Only as Components of Paper and Paperboard
Sec. 176.170 Components of paper and paperboard in contact with aqueous and fatty foods.


FDA PART 176 -- INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS
Subpart B--Substances for Use Only as Components of Paper and Paperboard
Sec. 176.180 Components of paper and paperboard in contact with dry food.
 
Physical Properties:
Appearance:white solid (est)
Assay: 99.00 to 100.00 sum of isomers
Food Chemicals Codex Listed: No
Melting Point: 72.00 °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
Odor Strength:high ,
recommend smelling in a 0.10 % solution or less
roasted burnt
Odor Description:at 0.10 % in propylene glycol. roasted burnt
Odor and/or flavor descriptions from others (if found).
Frutarom
2-BUTENOIC ACID (CROTONIC ACID)
Odor Description:Roast, Burnt
Suggested Uses: Bread, Coffee, Tropical Fruits
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: masking agents
stabilising agents
 
Suppliers:
CJ Latta & Associates
CROTONIC ACID
Frutarom
2-BUTENOIC ACID (CROTONIC ACID)
Odor: Roast, Burnt
Use: Suggested Uses: Bread, Coffee, Tropical Fruits
Grau Aromatics
CROTONIC ACID
Inoue Perfumery
CROTONIC ACID
Penta International
CROTONIC ACID
SRS Aromatics
CROTONIC ACID
Taytonn
2-Butenoic Acid
Odor: Burnt, Roast
Tengzhou Xiang Yuan Aroma Chemicals
2-Butenoic Acid
 
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
 average usual ppmaverage maximum ppm
baked goods: 5.000007.00000
beverages(nonalcoholic): 2.000005.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 0.200000.50000
fish products: --
frozen dairy: 5.000007.00000
fruit ices: --
gelatins / puddings: 5.000007.00000
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: 5.000007.00000
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

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

Scientific Opinion on Flavouring Group Evaluation 71: Consideration of aliphatic, linear, alpha,beta-unsaturated carboxylic acids and related esters
View page or View pdf

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

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

EPI System: View
NIOSH International Chemical Safety Cards:search
NLM Hazardous Substances Data Bank:Search
Env. Mutagen Info. Center: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:
 but-2-enoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:3724-65-0
Pubchem (cid):19499
Pubchem (sid):134985492
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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
FDA Indirect Additives used in Food Contact Substances:View
CHEMBL:View
KEGG (GenomeNet):C01771
HMDB (The Human Metabolome Database):HMDB10720
FooDB:FDB003283
Haz-Map:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
sulfurous
furfuryl thioacetate
FL/FR
For Flavor
No flavor group found for these
benzyl methyl sulfide
FL
2-iso
butyl-4,5-dimethyl oxazole
FL
fatty
fatty
4,5-
dimethyl-2-propyl oxazole
FL
green
2,5-
dimethyl-4-ethyl oxazole
FL
meaty
4-
allyl-2,6-dimethoxyphenol
FL
nutty
3-
acetyl-2,5-dimethyl thiophene
FL
roasted
furfuryl thioacetate
FL/FR
hexyl mercaptan
FL
 
Potential Uses:
FLbanana
FLbread
FLcheese
FLcoffee
FLfruit tropical fruit
 stabilising agents
FLwine
 
Occurrence (nature, food, other):note
 banana fruit
Search Trop Picture
 beer
Search PMC Picture
 bread
Search PMC Picture
 cheese
Search PMC Picture
 coffee
Search PMC Picture
 mussel - 0.16 mg/kg
Search PMC Picture
 tea black tea
Search Trop Picture
 wine
Search Picture
 
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:

PubMed:Dechlorination of chloroorganics, decolorization, and simultaneous bioremediation of Cr6+ from real tannery effluent employing indigenous Bacillus cereus isolate.
PubMed:QSAR, docking, dynamic simulation and quantum mechanics studies to explore the recognition properties of cholinesterase binding sites.
PubMed:Thotneosides A, B and C: potent antioxidants from nepalese crude drug, leaves of Aconogonon molle.
PubMed:Phytosphingosine derivatives ameliorate skin inflammation by inhibiting NF-κB and JAK/STAT signaling in keratinocytes and mice.
PubMed:Efficacy of some synthesized thiazoles against dermatophytes.
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.
PubMed:Mammalian multidrug resistance lipopentasaccharide inhibitors from Ipomoea alba seeds.
PubMed:Biotransformation of columbianadin by rat hepatic microsomes and inhibition of biotransformation products on NO production in RAW 264.7 cells in vitro.
PubMed:A High Molar Extinction Coefficient Bisterpyridyl Homoleptic Ru(II) Complex with trans-2-Methyl-2-butenoic Acid Functionality: Potential Dye for Dye-Sensitized Solar Cells.
PubMed:Stigonemapeptin, an Ahp-containing depsipeptide with elastase inhibitory activity from the bloom-forming freshwater cyanobacterium Stigonema sp.
PubMed:GC/MS method for positive detection of Bacillus anthracis endospores.
PubMed:NMR analysis of metabolic responses to extreme conditions of the temperature-dependent coral pathogen Vibrio coralliilyticus.
PubMed:Synthesis, photophysical and electrochemical properties of a mixed bipyridyl-phenanthrolyl ligand Ru(II) heteroleptic complex having trans-2-methyl-2-butenoic acid functionalities.
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.
PubMed:The curcuminoid CLEFMA selectively induces cell death in H441 lung adenocarcinoma cells via oxidative stress.
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.
PubMed:CLEFMA-an anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones.
PubMed:Isolation and structure elucidation of tumescenamides A and B, two peptides produced by Streptomyces tumescens YM23-260.
PubMed:Inhibitory effects of fatty acids on the activity of mushroom tyrosinase.
PubMed:New metabolites in dibenzofuran cometabolic degradation by a biphenyl-cultivated Pseudomonas putida strain B6-2.
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.
PubMed:Alternate Cu2 and Er2 spin carriers in a carboxylate-bridged chain: EPR study.
PubMed:Synthesis and antitumor activity of novel dibutyltin carboxylates of aminoglucosyl derivatives.
PubMed:Aroma-active components of Lycii fructus (kukija).
PubMed:A comparative kinetics study of isothermal drug release from poly(acrylic acid) and poly(acrylic-co-methacrylic acid) hydrogels.
PubMed:Basal expression of metallothionein suppresses butenolide-induced oxidative stress in liver homogenates in vitro.
PubMed:1-D polymers with alternate Cu2 and Ln2 units (Ln = Gd, Er, Y) and carboxylate linkages.
PubMed:Lipid peroxidation and antioxidant defense impairment in the hearts of chick embryos induced by in ovo exposure to Fusarium mycotoxin butenolide.
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.
PubMed:Glycosidic juvenogens: derivatives bearing alpha,beta-unsaturated ester functionalities.
PubMed:An efficient synthesis and reactions of novel indolylpyridazinone derivatives with expected biological activity.
PubMed:Toxic effects of Fusarium mycotoxin butenolide on rat myocardium and primary culture of cardiac myocytes.
PubMed:Synthesis, spectroscopic and structural elucidation of 3-ethylamino-2-(4-nitro-benzoyl)-but-2-enoic acid phenylamide.
PubMed:Dual irreversible kinase inhibitors: quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2.
PubMed:Sublethal effects of an organophosphorus insecticide (RPR-II) on biochemical parameters of tilapia, Oreochromis mossambicus.
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.
PubMed:Crotonic acid as a bioactive factor in carrot seeds (Daucus carota L.).
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.
 
Notes:
But-2-enoic acid is fatty acid formed by the action of fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the fatty acid biosynthesis. Specifically, it is the product of reaction between (R)-3-Hydroxybutyric acid and fatty acid synthase. [HMDB] Food flavour component Crotonic acid, or trans-2-butenoic acid, is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. (Wikipedia)
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