CHEBI:36062 - 3,4-dihydroxybenzoic acid

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ChEBI Name 3,4-dihydroxybenzoic acid
ChEBI ID CHEBI:36062
Definition A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1380, CHEBI:41912, CHEBI:16798, CHEBI:19879, CHEBI:20270, CHEBI:20272
Supplier Information ChemicalBook:CB3305861, eMolecules:502573, ZINC000000013246
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Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies. It is produced commercially from vanillin.
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Formula C7H6O4
Net Charge 0
Average Mass 154.120
Monoisotopic Mass 154.02661
InChI InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
InChIKey YQUVCSBJEUQKSH-UHFFFAOYSA-N
SMILES C(=O)(C1=CC(=C(C=C1)O)O)O
Metabolite of Species Details
Ficus mucuso (NCBI:txid309328) Found in fruit (BTO:0000486). Methanolic extract of air-dried and powdered figs(fruits) See: PubMed
Origanum vulgare (NCBI:txid39352) Found in aerial part (BTO:0001658). 95% EtOH extract of dried and powdered aerial parts See: PubMed
Oryza sativa (NCBI:txid4530) See: PubMed
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Alpinia (NCBI:txid94326) See: PubMed
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): EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor
An EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor that interferes with the action of procollagen-proline dioxygenase (EC 1.14.11.2).
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of shikimate dehydrogenase (EC 1.1.1.25).
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 3,4-dihydroxybenzoic acid (CHEBI:36062) has functional parent benzoic acid (CHEBI:30746)
3,4-dihydroxybenzoic acid (CHEBI:36062) has role antineoplastic agent (CHEBI:35610)
3,4-dihydroxybenzoic acid (CHEBI:36062) has role EC 1.1.1.25 (shikimate dehydrogenase) inhibitor (CHEBI:77484)
3,4-dihydroxybenzoic acid (CHEBI:36062) has role EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor (CHEBI:132365)
3,4-dihydroxybenzoic acid (CHEBI:36062) has role human xenobiotic metabolite (CHEBI:76967)
3,4-dihydroxybenzoic acid (CHEBI:36062) has role plant metabolite (CHEBI:76924)
3,4-dihydroxybenzoic acid (CHEBI:36062) is a catechols (CHEBI:33566)
3,4-dihydroxybenzoic acid (CHEBI:36062) is a dihydroxybenzoic acid (CHEBI:23778)
3,4-dihydroxybenzoic acid (CHEBI:36062) is conjugate acid of 3,4-dihydroxybenzoate (CHEBI:36241)
Incoming 1-(3,4-dihydroxybenzoyl)-β-D-glucopyranose (CHEBI:136876) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062)
ethyl 3,4-dihydroxybenzoate (CHEBI:132364) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062)
methyl 3,4-dihydroxybenzoate (CHEBI:132366) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062)
3,4-dihydroxybenzoate (CHEBI:36241) is conjugate base of 3,4-dihydroxybenzoic acid (CHEBI:36062)
IUPAC Name
3,4-dihydroxybenzoic acid
Synonyms Sources
3,4-Dihydroxybenzoic acid KEGG COMPOUND
4,5-Dihydroxybenzoic acid ChemIDplus
4-Carboxy-1,2-dihydroxybenzene ChemIDplus
Protocatechuic acid KEGG COMPOUND
Protocatechuic acid ChemIDplus
Protocatehuic acid ChemIDplus
Manual Xrefs Databases
3-4-DIHYDROXYBENZOATE MetaCyc
C00002668 KNApSAcK
C00230 KEGG COMPOUND
DHB PDBeChem
HMDB0001856 HMDB
Protocatechuic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1448841 Reaxys Registry Number Reaxys
99-50-3 CAS Registry Number KEGG COMPOUND
99-50-3 CAS Registry Number ChemIDplus
99-50-3 CAS Registry Number NIST Chemistry WebBook
Citations
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Wang D, Zou T, Yang Y, Yan X, Ling W (2011)
Cyanidin-3-O-β-glucoside with the aid of its metabolite protocatechuic acid, reduces monocyte infiltration in apolipoprotein E-deficient mice.
Biochemical pharmacology 82, 713-719 [PubMed:21569764]
[show Abstract]
Lin HH, Chen JH, Chou FP, Wang CJ (2011)
Protocatechuic acid inhibits cancer cell metastasis involving the down-regulation of Ras/Akt/NF-κB pathway and MMP-2 production by targeting RhoB activation.
British journal of pharmacology 162, 237-254 [PubMed:20840540]
[show Abstract]
Bankeu JJ, Khayala R, Lenta BN, Noungoué DT, Ngouela SA, Mustafa SA, Asaad K, Choudhary MI, Prigge ST, Hasanov R, Nkengfack AE, Tsamo E, Ali MS (2011)
Isoflavone dimers and other bioactive constituents from the figs of Ficus mucuso.
Journal of natural products 74, 1370-1378 [PubMed:21619045]
[show Abstract]
Chou TH, Ding HY, Lin RJ, Liang JY, Liang CH (2010)
Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
Journal of natural products 73, 1767-1774 [PubMed:20973550]
[show Abstract]
Myllyharju J (2008)
Prolyl 4-hydroxylases, key enzymes in the synthesis of collagens and regulation of the response to hypoxia, and their roles as treatment targets.
Annals of medicine 40, 402-417 [PubMed:19160570]
[show Abstract]
Vitaglione P, Donnarumma G, Napolitano A, Galvano F, Gallo A, Scalfi L, Fogliano V (2007)
Protocatechuic acid is the major human metabolite of cyanidin-glucosides.
The Journal of nutrition 137, 2043-2048 [PubMed:17709440]
[show Abstract]
Last Modified
05 July 2016