CHEBI:29069 - phthalic acid

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ChEBI Name phthalic acid
ChEBI ID CHEBI:29069
Definition A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:26093, CHEBI:44902, CHEBI:8174, CHEBI:14832
Supplier Information ChemicalBook:CB8672575, eMolecules:530358
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In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is C6H12O6; the molecule has a ring of six carbon atoms, each with an hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring. The compound is a carbohydrate, specifically a sugar alcohol (as distinct from aldoses like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers. A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors. In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them. A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS). However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS. The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, D-chiro-, L-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.
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Formula C8H6O4
Net Charge 0
Average Mass 166.13084
Monoisotopic Mass 166.02661
InChI InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChIKey XNGIFLGASWRNHJ-UHFFFAOYSA-N
SMILES OC(=O)c1ccccc1C(O)=O
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): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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ChEBI Ontology
Outgoing phthalic acid (CHEBI:29069) has role human xenobiotic metabolite (CHEBI:76967)
phthalic acid (CHEBI:29069) is a benzenedicarboxylic acid (CHEBI:26094)
phthalic acid (CHEBI:29069) is conjugate acid of phthalate(1−) (CHEBI:30800)
Incoming 3,4-dihydroxyphthalic acid (CHEBI:17416) has functional parent phthalic acid (CHEBI:29069)
4,5-dihydroxyphthalic acid (CHEBI:17199) has functional parent phthalic acid (CHEBI:29069)
4-hydroxyphthalic acid (CHEBI:27600) has functional parent phthalic acid (CHEBI:29069)
N-alkylphthalic monoamide (CHEBI:28900) has functional parent phthalic acid (CHEBI:29069)
cyhalodiamide (CHEBI:87541) has functional parent phthalic acid (CHEBI:29069)
phthalamide (CHEBI:38799) has functional parent phthalic acid (CHEBI:29069)
phthalate ester (CHEBI:35484) has functional parent phthalic acid (CHEBI:29069)
phthalylsulfathiazole (CHEBI:9336) has functional parent phthalic acid (CHEBI:29069)
phthalate(1−) (CHEBI:30800) is conjugate base of phthalic acid (CHEBI:29069)
IUPAC Name
benzene-1,2-dicarboxylic acid
Synonyms Sources
1,2-Benzenedicarboxylic acid KEGG COMPOUND
o-benzenedicarboxylic acid NIST Chemistry WebBook
ortho-phthalic acid ChEBI
Phthalic acid KEGG COMPOUND
PHTHALIC ACID PDBeChem
Manual Xrefs Databases
C01606 KEGG COMPOUND
DB02746 DrugBank
PHT PDBeChem
Phthalic_acid Wikipedia
View more database links
Registry Numbers Types Sources
27343 Gmelin Registry Number Gmelin
608199 Reaxys Registry Number Reaxys
88-99-3 CAS Registry Number KEGG COMPOUND
88-99-3 CAS Registry Number NIST Chemistry WebBook
88-99-3 CAS Registry Number ChemIDplus
Citations Types Sources
10682108 PubMed citation Europe PMC
15016950 PubMed citation Europe PMC
16804812 PubMed citation Europe PMC
9838120 PubMed citation Europe PMC
Last Modified
15 March 2021