2-butenal
2-butenaldehyde
 
Notes:
None found
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CAS Number: 4170-30-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 224-030-0
FDA UNII: 9G72074TUW
Beilstein Number: 1209254
MDL: MFCD00007003
XlogP3-AA: 0.50 (est)
Molecular Weight: 70.09102000
Formula: C4 H6 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
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US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: -76.50 °C. @ 760.00 mm Hg
Boiling Point: 104.00 °C. @ 760.00 mm Hg
Vapor Pressure: 30.000000 mmHg @ 20.00 °C. (est)
Flash Point: 40.00 °F. TCC ( 4.60 °C. ) (est)
logP (o/w): 0.771 (est)
Soluble in:
 water, 1.81E+05 mg/L @ 25 °C (exp)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Godavari Biorefineries
Crotonaldehyde
Sigma-Aldrich: Aldrich
For experimental / research use only.
Crotonaldehyde, mixture of cis and trans
ratio of cis- and trans-isomers (∼1:20), ≥99.5% (GC)
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Safety Information:
Preferred SDS: View
 
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:
intravenous-cat LDLo  30 mg/kg
BLOOD: OTHER CHANGES
Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 275, 1952.

oral-mouse LD50  104 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(8), Pg. 53, 1982.

oral-rat LD50  80 mg/kg
LUNGS, THORAX, OR RESPIRATION: CYANOSIS CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 62(3), Pg. 3, 1997.

Dermal Toxicity:
skin-guinea pig LD50 30 uL/kg
Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.

skin-rabbit LD50 380 uL/kg
Union Carbide Data Sheet. Vol. 4/21/1967

Inhalation Toxicity:
inhalation-mouse LC50 580 mg/m3/2H
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(8), Pg. 53, 1982.

inhalation-rat LC50 200 mg/m3/2H
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(8), Pg. 53, 1982.

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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 2-butenal usage levels up to:
 not for fragrance use.
 
Recommendation for 2-butenal flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
NIOSH International Chemical Safety Cards: search
NIOSH Pocket Guide: search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 4170-30-3
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 20138
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 but-2-enal
Chemidplus: 0004170303
EPA/NOAA CAMEO: hazardous materials
RTECS: 4170-30-3
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References:
 but-2-enal
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 4170-30-3
Pubchem (cid): 20138
Pubchem (sid): 134984616
Pherobase: View
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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
KEGG (GenomeNet): C19377
HMDB (The Human Metabolome Database): Search
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 apricot fruit
Search Trop  Picture
 chicory root oil @ 0.013%
Data  GC  Search Trop  Picture
 milk oxidized skim milk
Search  PMC Picture
 pear fruit
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Synonyms:
 but-2-enal
2-buten-1-al
2-butenal propylene aldelhyde
2-butenaldehyde
 crotonaldehyde
 crotonic aldehyde
 crotyl aldehyde
1-formyl propene
1-formylpropene
beta-methyl acrolein
 methyl propenal
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Articles:
US Patents: 8,173,822 - 1,3-oxathiane compounds and their use in flavor and fragrance compositions
PubMed: Activation of the Keap1/Nrf2 pathway through covalent modification of the 2-alkenal group of aliphatic electrophiles in Coriandrum sativum L.
PubMed: Transport of hop aroma compounds across Caco-2 monolayers.
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: Growth Inhibitory Effect of (E)-2,4-bis(p-hydroxyphenyl)-2-Butenal Diacetate through Induction of Apoptotic Cell Death by Increasing DR3 Expression in Human Lung Cancer Cells.
PubMed: Effects of aliphatic aldehydes on the growth and patulin production of Penicillium expansum in apple juice.
PubMed: Mutagenic/recombinogenic effects of four lipid peroxidation products in Drosophila.
PubMed: Small reactive carbonyl compounds as tissue lipid oxidation products; and the mechanisms of their formation thereby.
PubMed: On-fiber furan formation from volatile precursors: a critical example of artefact formation during Solid-Phase Microextraction.
PubMed: The potential of biodetoxification activity as a probiotic property of Lactobacillus reuteri.
PubMed: [13C2]-Acetaldehyde promotes unequivocal formation of 1,N2-propano-2'-deoxyguanosine in human cells.
PubMed: Gas chromatography/sniffing port analysis of aroma compounds released under mouth conditions.
PubMed: Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification.
PubMed: Direct aldehyde homologation utilized to construct a conjugated-tetraene hydrocarbon insect pheromone.
PubMed: Difference in the volatile composition of pine-mushrooms (Tricholoma matsutake Sing.) according to their grades.
PubMed: Changes induced by UV radiation during virgin olive oil storage.
PubMed: How cysteine reacts with citral: an unexpected reaction of beta,beta-disubstituted acroleins with cysteine leading to hexahydro-1,4-thiazepines.
PubMed: The unbearable lightness of "light" cigarettes: a comparison of smoke yields in six varieties of Canadian "light" cigarettes.
PubMed: Origin and mechanistic pathways of formation of the parent furan--a food toxicant.
PubMed: Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide.
PubMed: Aldehyde-induced xanthine oxidase activity in raw milk.
PubMed: A novel, inducible, citral lyase purified from spores of Penicillium digitatum.
PubMed: Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O.
PubMed: Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry.
PubMed: The influence of the solvents DMSO and ethanol on the genotoxicity of alpha,beta-unsaturated aldehydes in the SOS chromotest.
PubMed: Cancer risk assessment for the environmental mutagen and carcinogen crotonaldehyde on the basis of TD(50) and comparison with 1,N(2)-propanodeoxyguanosine adduct levels.
PubMed: Endogenous formation of protein adducts with carcinogenic aldehydes: implications for oxidative stress.
PubMed: Development of a 32P-postlabelling method for the detection of 1,N2-propanodeoxyguanosine adducts of crotonaldehyde in vivo.
PubMed: Volatile aldehydes are promising broad-spectrum postharvest insecticides.
PubMed: Detection of 1,N(2)-propanodeoxyguanosine adducts in DNA of Fischer 344 rats by an adapted (32)P-post-labeling technique after per os application of crotonaldehyde.
PubMed: Detection of 1,N2-propanodeoxyguanosine adducts of 2-hexenal in organs of Fischer 344 rats by a 32P-post-labeling technique.
PubMed: Cellular response to the redox active lipid peroxidation products: induction of glutathione S-transferase P by 4-hydroxy-2-nonenal.
PubMed: (E)-2-hexenal-induced DNA damage and formation of cyclic 1,N2-(1,3-propano)-2'-deoxyguanosine adducts in mammalian cells.
PubMed: Crotonaldehyde: a carcinogenic and mutagenic air, water and food pollutant.
PubMed: The influence of glutathione and detoxifying enzymes on DNA damage induced by 2-alkenals in primary rat hepatocytes and human lymphoblastoid cells.
PubMed: Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment.
PubMed: Formation of odorous compounds from hydrogen sulphide and 2-butenal.
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