Protocatechuic aldehyde

Protocatechuic aldehyde
Chemical structure of protocatechuic aldehyde
Names
Preferred IUPAC name
3,4-Dihydroxybenzaldehyde
Other names
Protocatechualdehyde
Rancinamycin IV
3,4-Dihydroxybenzyl aldehyde
Identifiers
CAS Number
  • 139-85-5 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 774381
ChEBI
  • CHEBI:50205
ChEMBL
  • ChEMBL222021 checkY
ChemSpider
  • 8438 checkY
DrugBank
  • DB11268
ECHA InfoCard 100.004.889 Edit this at Wikidata
EC Number
  • 205-377-7
Gmelin Reference
 123001
KEGG
  • C16700 checkY
PubChem CID
  • 8768
UNII
  • 4PVP2HCH4T checkY
CompTox Dashboard (EPA)
  • DTXSID4074512 Edit this at Wikidata
InChI
  • InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H ☒N
    Key: IBGBGRVKPALMCQ-UHFFFAOYSA-N ☒N
  • InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
    Key: IBGBGRVKPALMCQ-UHFFFAOYAN
  • 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 [77 °F], 100 kPa).
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Infobox references
Chemical compound

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. ^ 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

  • v
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  • e