fbpx
Wikipedia

Protocatechuic aldehyde

April 10, 2024

Protocatechuic aldehyde is a phenolic aldehyde, a compound released from cork stoppers into wine.[1]

Protocatechuic aldehyde
Names
Preferred IUPAC name
3,4-Dihydroxybenzaldehyde
Other names
Protocatechualdehyde
Rancinamycin IV
3,4-Dihydroxybenzyl aldehyde
Identifiers
  • 139-85-5 Y
3D model (JSmol)
  • Interactive image
774381
ChEBI
  • CHEBI:50205
ChEMBL
  • ChEMBL222021 Y
ChemSpider
  • 8438 Y
DrugBank
  • DB11268
ECHA InfoCard 100.004.889
EC Number
  • 205-377-7
123001
KEGG
  • C16700 Y
  • 8768
UNII
  • 4PVP2HCH4T Y
  • DTXSID4074512
  • 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
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).
N verify (what is YN ?)

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 edit

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

References edit

  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 edit

 

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

April 10, 2024
protocatechuic, aldehyde, phenolic, aldehyde, compound, released, from, cork, stoppers, into, wine, namespreferred, iupac, name, dihydroxybenzaldehydeother, names, protocatechualdehyderancinamycin, dihydroxybenzyl, aldehydeidentifierscas, number, model, jsmol,. Protocatechuic aldehyde is a phenolic aldehyde a compound released from cork stoppers into wine 1 Protocatechuic aldehyde NamesPreferred IUPAC name 3 4 DihydroxybenzaldehydeOther names ProtocatechualdehydeRancinamycin IV3 4 Dihydroxybenzyl aldehydeIdentifiersCAS Number 139 85 5 Y3D model JSmol Interactive imageBeilstein Reference 774381ChEBI CHEBI 50205ChEMBL ChEMBL222021 YChemSpider 8438 YDrugBank DB11268ECHA InfoCard 100 004 889EC Number 205 377 7Gmelin Reference 123001KEGG C16700 YPubChem CID 8768UNII 4PVP2HCH4T YCompTox Dashboard EPA DTXSID4074512InChI InChI 1S C7H6O3 c8 4 5 1 2 6 9 7 10 3 5 h1 4 9 10H NKey IBGBGRVKPALMCQ UHFFFAOYSA N NInChI 1 C7H6O3 c8 4 5 1 2 6 9 7 10 3 5 h1 4 9 10HKey IBGBGRVKPALMCQ UHFFFAOYANSMILES C1 CC C C C1C O O OPropertiesChemical formula C7H6O3Molar mass 138 12 g molRelated compoundsRelated compounds 2 4 DihydroxybenzaldehydeExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 editProtocatechuic aldehyde regulates G protein coupled estrogen receptor 1 GPER 1 and exhibits protective effects in endothelial dysfunction and atherosclerosis 4 References edit Conde E Cadahia E Garcia Vallejo MC Fernandez de Simon 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 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 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 amp Pharmaceutical Bulletin 31 10 1968 72 doi 10 1248 bpb 31 1968 PMID 18827365 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 editPhenolic compounds in wine nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Protocatechuic aldehyde amp oldid 1169571168, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.