Chemistry:Protocatechuic aldehyde

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Protocatechuic aldehyde
Chemical structure of protocatechuic aldehyde
Names
Preferred IUPAC name
3,4-Dihydroxybenzaldehyde
Other names
Protocatechualdehyde
Rancinamycin IV
3,4-Dihydroxybenzyl aldehyde
Identifiers
3D model (JSmol)
774381
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 205-377-7
123001
KEGG
UNII
Properties
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 [77 °F], 100 kPa).
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Protocatechuic aldehyde is a phenolic aldehyde, a compound released from cork stoppers into wine.[1]

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.[2] It is also found in the mushroom Phellinus linteus.[3]

Pharmacological effects

Protocatechuic aldehyde regulates G protein-coupled estrogen receptor-1 (GPER-1) and exhibits protective effects in endothelial dysfunction and atherosclerosis.[4]

References

  1. "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances.". Journal of Agricultural and Food Chemistry 46 (8): 3166–71. August 1998. doi:10.1021/jf970863k. 
  2. "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. January 2000. doi:10.1016/s0168-1656(99)00177-7. PMID 10656328. 
  3. "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological & Pharmaceutical Bulletin 31 (10): 1968–72. October 2008. doi:10.1248/bpb.31.1968. PMID 18827365. 
  4. "G protein-coupled estrogen receptor-1 is involved in the protective effect of protocatechuic aldehyde against endothelial dysfunction". PLOS ONE 9 (11): e113242. 2014. doi:10.1371/journal.pone.0113242. PMID 25411835. Bibcode2014PLoSO...9k3242K. 

See also

  • Phenolic compounds in wine