2-Butenedioic acid
Basic information
- CAS
6915-18-0- Standard SMILES
O=C(O)C=CC(=O)O- InChIKey
VZCYOOQTPOCHFL-UHFFFAOYSA-N- Molecular formula
- C4H4O4
- Average molar mass
- 116.07 g/mol
- Monoisotopic mass
- 116.01095861
Overview
Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Names & identifiers
- Preferred name
- 2-Butenedioic acid
- IUPAC
- but-2-enedioic acid
- English name
- Maleic acid
- Molecular formula
- C4H4O4
- Molecular weight
- 116.07
Names & synonyms
2-Butenedioic acidButenedioic acidDTXSID80481576915-18-0CHEBI:22958RefChem:1062582DTXCID8028133Maleic acid-2,3-d2C4H4O4(Z)-2-Butenedioic acid homopolymer2-aButenedioic acid1,2-Ethenedicarboxylic
Show more names
SCHEMBL615MALEIC ACID, WHITENCIOpen2_003792NCIOpen2_004870SCHEMBL2079401SCHEMBL8834096Polymaleic acid, 50% in H2OSCHEMBL11318995
Database identifiers
- CAS
6915-18-0- PubChem CID
- 723
- DTXSID
DTXSID8048157
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 119
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
Uses
Use (kg; approx.) in Germany (2009): >1000
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-).
Related reactions
167 records
Compound notes
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