CHEBI:18308 - acrylic acid

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ChEBI Name acrylic acid
ChEBI ID CHEBI:18308
Definition A α,β-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:35853, CHEBI:35938, CHEBI:40714, CHEBI:8487, CHEBI:19766, CHEBI:19768
Supplier Information No supplier information found for this compound.
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Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
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Formula C3H4O2
Net Charge 0
Average Mass 72.06266
Monoisotopic Mass 72.02113
InChI InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChIKey NIXOWILDQLNWCW-UHFFFAOYSA-N
SMILES OC(=O)C=C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing acrylic acid (CHEBI:18308) has role metabolite (CHEBI:25212)
acrylic acid (CHEBI:18308) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
acrylic acid (CHEBI:18308) is conjugate acid of acrylate (CHEBI:37080)
Incoming α-(4-methoxyphenyl)-6-methyl-2-pyridineacrylic acid (CHEBI:74085) has functional parent acrylic acid (CHEBI:18308)
(2E)-3-[(2S,3aR,7aS)-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3,3a,7a-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid (CHEBI:43613) has functional parent acrylic acid (CHEBI:18308)
(2Z)-2,3-dihydroxyacrylic acid (CHEBI:131382) has functional parent acrylic acid (CHEBI:18308)
(E)-3-(indol-2-yl)acrylic acid (CHEBI:90333) has functional parent acrylic acid (CHEBI:18308)
(E)-3-(indol-3-yl)acrylic acid (CHEBI:132244) has functional parent acrylic acid (CHEBI:18308)
(Z)-3-aminoacrylic acid (CHEBI:59893) has functional parent acrylic acid (CHEBI:18308)
(Z)-3-aminoperacrylic acid (CHEBI:59892) has functional parent acrylic acid (CHEBI:18308)
1-Octen-3-one (CHEBI:88900) has functional parent acrylic acid (CHEBI:18308)
2-(4-chlorophenyl)-3,3-dichloropropenoic acid (CHEBI:28983) has functional parent acrylic acid (CHEBI:18308)
2-chloroacrylic acid (CHEBI:73963) has functional parent acrylic acid (CHEBI:18308)
2-ethylacrylic acid (CHEBI:84978) has functional parent acrylic acid (CHEBI:18308)
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid (CHEBI:27683) has functional parent acrylic acid (CHEBI:18308)
2-hydroxyacrylic acid (CHEBI:86354) has functional parent acrylic acid (CHEBI:18308)
3,3-dichloroacrylic acid (CHEBI:186566) has functional parent acrylic acid (CHEBI:18308)
3,3-diiodoacrylic acid (CHEBI:176854) has functional parent acrylic acid (CHEBI:18308)
3-(4,6-dihydroxy-3-oxocyclohexa-1,4-dien-1-yl)acrylic acid (CHEBI:133314) has functional parent acrylic acid (CHEBI:18308)
3-(oximinoacetamido)acrylamide (CHEBI:215763) has functional parent acrylic acid (CHEBI:18308)
3-[(1-carboxyvinyl)oxy]benzoic acid (CHEBI:77107) has functional parent acrylic acid (CHEBI:18308)
3-Acrylamidopropyl trimethylammonium (CHEBI:188216) has functional parent acrylic acid (CHEBI:18308)
3-bromo-2E-acrylic acid (CHEBI:195735) has functional parent acrylic acid (CHEBI:18308)
3-chloroacrylic acid (CHEBI:19982) has functional parent acrylic acid (CHEBI:18308)
3-Iodo-2E-acrylic acid (CHEBI:165394) has functional parent acrylic acid (CHEBI:18308)
3-Methyl-3-buten-2-one (CHEBI:88437) has functional parent acrylic acid (CHEBI:18308)
3-nitroacrylic acid (CHEBI:17610) has functional parent acrylic acid (CHEBI:18308)
3-Octen-2-one (CHEBI:89712) has functional parent acrylic acid (CHEBI:18308)
4-Methyl-3-penten-2-one, 9CI (CHEBI:89993) has functional parent acrylic acid (CHEBI:18308)
6-Methyl-3,5-heptadien-2-one (CHEBI:89984) has functional parent acrylic acid (CHEBI:18308)
enol-phenylpyruvic acid (CHEBI:32815) has functional parent acrylic acid (CHEBI:18308)
O-acryloyl-L-carnitine (CHEBI:85466) has functional parent acrylic acid (CHEBI:18308)
O-propenoylcarnitine (CHEBI:86073) has functional parent acrylic acid (CHEBI:18308)
acrylamide (CHEBI:28619) has functional parent acrylic acid (CHEBI:18308)
acryloyl-CoA (CHEBI:15513) has functional parent acrylic acid (CHEBI:18308)
butyl acrylate (CHEBI:3245) has functional parent acrylic acid (CHEBI:18308)
caffeic acid quinone (CHEBI:133316) has functional parent acrylic acid (CHEBI:18308)
Cis-3-chloroacrylic-acid (CHEBI:194631) has functional parent acrylic acid (CHEBI:18308)
CJ-15,801 (CHEBI:189351) has functional parent acrylic acid (CHEBI:18308)
Enamidin (CHEBI:216602) has functional parent acrylic acid (CHEBI:18308)
Ethyl 3,3-diiodoacrylate (CHEBI:187247) has functional parent acrylic acid (CHEBI:18308)
Ethyl 3-iodo-2E-acrylate (CHEBI:187432) has functional parent acrylic acid (CHEBI:18308)
lauryl acrylate (CHEBI:191951) has functional parent acrylic acid (CHEBI:18308)
methacrylic acid (CHEBI:25219) has functional parent acrylic acid (CHEBI:18308)
phosphoenolpyruvic acid (CHEBI:44897) has functional parent acrylic acid (CHEBI:18308)
ureidoacrylic acid (CHEBI:59890) has functional parent acrylic acid (CHEBI:18308)
ureidoperacrylic acid (CHEBI:59889) has functional parent acrylic acid (CHEBI:18308)
valanimycin (CHEBI:133621) has functional parent acrylic acid (CHEBI:18308)
sulfoacrylate (CHEBI:193093) is a acrylic acid (CHEBI:18308)
acrylate (CHEBI:37080) is conjugate base of acrylic acid (CHEBI:18308)
acryloyl group (CHEBI:48077) is substituent group from acrylic acid (CHEBI:18308)
IUPAC Name
prop-2-enoic acid
Synonyms Sources
2-Propenoic acid KEGG COMPOUND
acroleic acid ChemIDplus
Acrylate KEGG COMPOUND
Acrylic acid KEGG COMPOUND
ACRYLIC ACID PDBeChem
ethylenecarboxylic acid NIST Chemistry WebBook
Propenoate KEGG COMPOUND
Propenoate KEGG COMPOUND
Propenoic acid ChemIDplus
Vinylformic acid KEGG COMPOUND
Manual Xrefs Databases
Acrylic_acid Wikipedia
AKR PDBeChem
C00511 KEGG COMPOUND
DB02579 DrugBank
HMDB0031647 HMDB
LMFA01030193 LIPID MAPS
MY148411 MetaCyc
MY149879 MetaCyc
View more database links
Registry Numbers Types Sources
1817 Gmelin Registry Number Gmelin
635743 Reaxys Registry Number Reaxys
79-10-7 CAS Registry Number NIST Chemistry WebBook
79-10-7 CAS Registry Number ChemIDplus
Citations
Yu Y, Huang L, Wu W, Jiang H (2014)
Palladium-catalyzed oxidative annulation of acrylic acid and amide with alkynes: a practical route to synthesize α-pyrones and pyridones.
Organic letters 16, 2146-2149 [PubMed:24673501]
[show Abstract]
Johnston BF, Marshall WG, Parsons S, Urquhart AJ, Oswald ID (2014)
Investigation of acrylic acid at high pressure using neutron diffraction.
The journal of physical chemistry. B 118, 4044-4051 [PubMed:24650085]
[show Abstract]
Last Modified
31 May 2022