CHEBI:22211 - aconitic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name aconitic acid
ChEBI ID CHEBI:22211
Definition A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5100903, eMolecules:36758208, eMolecules:474902, eMolecules:5748014, eMolecules:884420, ZINC000008577218
Download Molfile XML SDF
Wikipedia License
Folate, also known as vitamin B9 and folacin, is one of the B vitamins. Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and storage. Folate is required for the body to make DNA and RNA and metabolise amino acids necessary for cell division and maturation of blood cells. As the human body cannot make folate, it is required in the diet, making it an essential nutrient. It occurs naturally in many foods. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements. Folate in the form of folic acid is used to treat anemia caused by folate deficiency. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby. NTDs include anencephaly and spina bifida, among other defects. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs. More than 80 countries use either mandatory or voluntary fortification of certain foods with folic acid as a measure to decrease the rate of NTDs. Long-term supplementation with relatively large amounts of folic acid is associated with a small reduction in the risk of stroke and an increased risk of prostate cancer. There are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency. Not consuming enough folate can lead to folate deficiency. This may result in a type of anemia in which red blood cells become abnormally large. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Folate deficiency in children may develop within a month of poor dietary intake. In adults, normal total body folate is between 10 and 30 mg with about half of this amount stored in the liver and the remainder in blood and body tissues. In plasma, the natural folate range is 150 to 450 nM. Folate was discovered between 1931 and 1943. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions. The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables.
Read full article at Wikipedia
Formula C6H6O6
Net Charge 0
Average Mass 174.10824
Monoisotopic Mass 174.01644
InChI InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey GTZCVFVGUGFEME-UHFFFAOYSA-N
SMILES OC(=O)CC(=CC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aconitic acid (CHEBI:22211) is a tricarboxylic acid (CHEBI:27093)
aconitic acid (CHEBI:22211) is conjugate acid of aconitate(3−) (CHEBI:22210)
Incoming cis-aconitic acid (CHEBI:32805) is a aconitic acid (CHEBI:22211)
trans-aconitic acid (CHEBI:32806) is a aconitic acid (CHEBI:22211)
aconitate(3−) (CHEBI:22210) is conjugate base of aconitic acid (CHEBI:22211)
IUPAC Name
prop-1-ene-1,2,3-tricarboxylic acid
Synonyms Sources
1-propene-1,2,3-tricarboxylic acid ChemIDplus
3-carboxy-2-pentenedioic acid ChemIDplus
achilleic acid ChemIDplus
citridic acid ChemIDplus
equisetic acid ChemIDplus
Manual Xref Database
Aconitic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1725828 Reaxys Registry Number Reaxys
185280 Gmelin Registry Number Gmelin
499-12-7 CAS Registry Number ChemIDplus
Citations Types Sources
24702026 PubMed citation Europe PMC
24710945 PubMed citation Europe PMC
25011271 PubMed citation Europe PMC
Last Modified
17 July 2014