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3,4-Dihydroxybenzaldehyde

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(Redirected from Protocatechuic aldehyde)
3,4-Dihydroxybenzaldehyde
Chemical structure of protocatechuic aldehyde
Names
Preferred IUPAC name 3,4-Dihydroxybenzaldehyde
Other names Protocatechuic aldehyde
Protocatechualdehyde
Rancinamycin IV
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 774381
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.889 Edit this at Wikidata
EC Number
  • 205-377-7
Gmelin Reference 123001
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10HKey: IBGBGRVKPALMCQ-UHFFFAOYSA-N
  • InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10HKey: IBGBGRVKPALMCQ-UHFFFAOYAN
SMILES
  • C1=CC(=C(C=C1C=O)O)O
Properties
Chemical formula C7H6O3
Molar mass 138.12 g/mol
Related compounds
Related compounds 2,4-Dihydroxybenzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. It is an isomer of 2,4-dihydroxybenzaldehyde.

This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus.

Pharmacological effects

Protocatechuic aldehyde regulates G protein-coupled estrogen receptor-1 (GPER-1) and exhibits protective effects in endothelial dysfunction and atherosclerosis.

References

  1. Conde E, Cadahía E, García-Vallejo MC, Fernández de Simón B (August 1998). "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances". Journal of Agricultural and Food Chemistry. 46 (8): 3166–71. doi:10.1021/jf970863k.
  2. Rao SR, Ravishankar GA (January 2000). "Biotransformation of protocatechuic aldehyde and caffeic acid to vanillin and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens". Journal of Biotechnology. 76 (2–3): 137–46. doi:10.1016/s0168-1656(99)00177-7. PMID 10656328. S2CID 28017446.
  3. Lee YS, Kang YH, Jung JY, Lee S, Ohuchi K, Shin KH, et al. (October 2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological & Pharmaceutical Bulletin. 31 (10): 1968–72. doi:10.1248/bpb.31.1968. PMID 18827365.
  4. Kong BS, Cho YH, Lee EJ (2014). "G protein-coupled estrogen receptor-1 is involved in the protective effect of protocatechuic aldehyde against endothelial dysfunction". PLOS ONE. 9 (11): e113242. Bibcode:2014PLoSO...9k3242K. doi:10.1371/journal.pone.0113242. PMC 4239058. PMID 25411835.

See also

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