(E)-2-buten-1-al
trans-2-butenal
Identification
| Name | (E)-2-buten-1-al |
| IUPAC | (E)-but-2-enal |
| CAS Number | 123-73-9 |
| EINECS | 204-647-1 |
| FDA UNII | 6PUW625907 |
| Molecular Formula | C4 H6 O |
| Molecular Weight | 70.09102000 |
| MDL Number | MFCD00007003 |
| Nikkaji Number | J9.294K |
| CoE Number | 11736 |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.84600 @ 25.00 °C. |
| Refractive Index | 1.43650 @ 20.00 °C. |
| Melting Point | -101.00 to -98.00 °C. @ 760.00 mm Hg |
| Boiling Point | 102.20 °C. @ 760.00 mm Hg |
| Vapor Pressure | 31.438999 mmHg @ 25.00 °C. (est) |
| Vapor Density | 2.41 ( Air = 1 ) |
| Flash Point | 48.00 °F. TCC ( 8.89 °C. ) |
| logP (o/w) | 0.600 |
| Soluble in | alcohol |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-mouse LD50 240 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 380 mg/kg |
| Inhalation Toxicity | inhalation-rat LC50 4000 mg/m3/30M |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: ATAXIA\nBEHAVIORAL: EXCITEMENT']
Safety in Use
| Category | flavoring agents |
| Recommendation for (E)-2-buten-1-al usage levels up to | not for fragrance use. |
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Potential Uses
Natural Occurrence
Synonyms
(2E)-
but-2-enal
(E)-
but-2-enal
trans-
but-2-enal
trans-2-
buten-1-al
(2E)-2-
butenal
(E)-2-
butenal
trans-2-
butenal
2-
butenal, (2E)-
trans-2-
butenaldehyde
(E)-
crotonal
(E)-
crotonaldehyde
trans-
crotonaldehyde
crotonaldehyde, (E)-
(E)-
crotonic aldehyde
topanel
PubMed:
Activation of the Keap1/Nrf2 pathway through covalent modification of the 2-alkenal group of aliphatic electrophiles in Coriandrum sativum L.
J-Stage:
Effects of Aliphatic Aldehydes on the Growth and Patulin Production of Penicillium expansum in Apple Juice
PubMed:
Development of three stable isotope dilution assays for the quantitation of (E)-2-butenal (crotonaldehyde) in heat-processed edible fats and oils as well as in food.
PubMed:
Signatures of isomerization in photodissociation of trans- crotonaldehyde probed by multiphoton ionization mass spectrometry.
PubMed:
Effects of aliphatic aldehydes on the growth and patulin production of Penicillium expansum in apple juice.
PubMed:
Tandem catalysis in domino olefin cross-metathesis/intramolecular oxa-conjugate cyclization: concise synthesis of 2,6-cis-substituted tetrahydropyran derivatives.
PubMed:
Contribution of cation-Ï interactions in iminium catalysis.
PubMed:
Human aldo-keto reductase AKR7A2 protects against the cytotoxicity and mutagenicity of reactive aldehydes and lowers intracellular reactive oxygen species in hamster V79-4 cells.
PubMed:
Kinetics studies of the gas-phase reactions of NO3 radicals with series of 1-alkenes, dienes, cycloalkenes, alkenols, and alkenals.
PubMed:
A computational study of the mechanism of the unimolecular elimination of α,β-unsaturated aldehydes in the gas phase.
PubMed:
Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal.
PubMed:
Atmospheric reaction of OH radicals with 1,3-butadiene and 4-hydroxy-2-butenal.
PubMed:
Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence.
PubMed:
Modulation of pumpkin glutathione S-transferases by aldehydes and related compounds.
PubMed:
1,N2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage.
PubMed:
Aldehyde-induced xanthine oxidase activity in raw milk.
PubMed:
Structure-antimutagenic activity relationships of benzalacetone derivatives against UV-induced mutagenesis in E. coli WP2uvrA and gamma-induced mutagenesis in Salmonella typhimurium TA2638.
PubMed:
Volatile aldehydes are promising broad-spectrum postharvest insecticides.
PubMed:
Role of 1,N2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans.
PubMed:
Structural and kinetic determinants of aldehyde reduction by aldose reductase.
PubMed:
Purification and characterization of two enone reductases from Saccharomyces cerevisiae.
PubMed:
Structures of acrolein-guanine adducts: a semi-empirical self-consistent field and nuclear magnetic resonance spectral study.
PubMed:
Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1.
PubMed:
Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal.
PubMed:
Genotoxic effects of the alpha, beta-unsaturated aldehydes 2-trans-butenal, 2-trans-hexenal and 2-trans, 6-cis-nonadienal.
PubMed:
Mechanism-based inactivation of porcine kidney diamine oxidase by 1,4-diamino-2-butene.
PubMed:
Effects of age and dietary restriction on liver glutathione transferase activities in Lobund-Wistar rats.
PubMed:
Human Mu-class glutathione S-transferases present in liver, skeletal muscle and testicular tissue.
PubMed:
Identification and characterization of deoxyguanosine-crotonaldehyde adducts. Formation of 7,8 cyclic adducts and 1,N2,7,8 bis-cyclic adducts.
PubMed:
The reaction of xanthine oxidase with aldehydic products of lipid peroxidation.
PubMed:
Detection of exocyclic guanine adducts in hydrolysates of hepatic DNA of rats treated with N-nitrosopyrrolidine and in calf thymus DNA reacted with alpha-acetoxy-N-nitrosopyrrolidine.
PubMed:
Inhibition of microsomal cytochrome c reductase activity by a series of alpha, beta-unsaturated aldehydes.
PubMed:
Mutagenicity and toxicity studies of several alpha,beta-unsaturated aldehydes in the Salmonella typhimurium mutagenicity assay.
PubMed:
Inhibition by reactive aldehydes of superoxide anion radical production in stimulated human neutrophils.