3,4-Dihydroxybenzaldehyde

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 417955916 | Name = 3,4-Dihydroxybenzaldehyde | ImageFile = Protocatechualdehyd.svg | ImageSize = 150px | ImageName = Chemical structure of protocatechuic aldehyde | ImageAlt = Chemical structure of protocatechuic aldehyde | PIN = 3,4-Dihydroxybenzaldehyde | OtherNames = Protocatechuic aldehyde Protocatechualdehyde Rancinamycin IV |Section1={{Chembox Identifiers | CASNo = 139-85-5 | CASNo_Ref = {{cascite|correct|CAS}} | Beilstein = 774381 | ChEBI = 50205 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 222021 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8438 | DrugBank = DB11268 | EC_number = 205-377-7 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C16700 | PubChem = 8768 | Gmelin = 123001 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4PVP2HCH4T | SMILES = C1=CC(=C(C=C1C=O)O)O | InChI = 1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H | InChIKey = IBGBGRVKPALMCQ-UHFFFAOYAN | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = IBGBGRVKPALMCQ-UHFFFAOYSA-N | MeSHName = }} |Section2={{Chembox Properties | Formula = C7H6O3 | MolarMass = 138.12 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section8={{Chembox Related | OtherCompounds = 2,4-Dihydroxybenzaldehyde }} }} '''3,4-Dihydroxybenzaldehyde''', also known as '''protocatechuic aldehyde''', is a phenolic aldehyde, a compound released from cork stoppers into wine.<ref>{{cite journal | vauthors = Conde E, Cadahía E, García-Vallejo MC, Fernández de Simón B | title = Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances. | journal = Journal of Agricultural and Food Chemistry | date = August 1998 | volume = 46 | issue = 8 | pages = 3166–71 | doi = 10.1021/jf970863k }}</ref> 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.<ref name="pmid10656328">{{cite journal | vauthors = Rao SR, Ravishankar GA | title = Biotransformation of protocatechuic aldehyde and caffeic acid to vanillin and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens | journal = Journal of Biotechnology | volume = 76 | issue = 2–3 | pages = 137–46 | date = January 2000 | pmid = 10656328 | doi = 10.1016/s0168-1656(99)00177-7 | s2cid = 28017446 }}</ref> It is also found in the mushroom ''Phellinus linteus''.<ref name="pmid18827365">{{cite journal | vauthors = Lee YS, Kang YH, Jung JY, Lee S, Ohuchi K, Shin KH, Kang IJ, Park JH, Shin HK, Lim SS | display-authors = 6 | title = Protein glycation inhibitors from the fruiting body of Phellinus linteus | journal = Biological & Pharmaceutical Bulletin | volume = 31 | issue = 10 | pages = 1968–72 | date = October 2008 | pmid = 18827365 | doi = 10.1248/bpb.31.1968 | doi-access = free }}</ref>

== Pharmacological effects == Protocatechuic aldehyde regulates G protein-coupled estrogen receptor-1 (GPER-1) and exhibits protective effects in endothelial dysfunction and atherosclerosis.<ref name="pmid25411835">{{cite journal | vauthors = Kong BS, Cho YH, Lee EJ | title = G protein-coupled estrogen receptor-1 is involved in the protective effect of protocatechuic aldehyde against endothelial dysfunction | journal = PLOS ONE | volume = 9 | issue = 11 | article-number = e113242 | date = 2014 | pmid = 25411835 | pmc = 4239058 | doi = 10.1371/journal.pone.0113242 | bibcode = 2014PLoSO...9k3242K | doi-access = free }}</ref>

== References == {{reflist}}

== See also == * Phenolic compounds in wine

{{DEFAULTSORT:Dihydroxybenzaldehyde, 3,4-}} Category:4-Hydroxybenzaldehyde derivatives Category:Catechols