Protocatechuic aldehyde

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

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

^ 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.
^ 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 & 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.

Names

Preferred IUPAC name 3,4-Dihydroxybenzaldehyde
Other names Protocatechualdehyde Rancinamycin IV 3,4-Dihydroxybenzyl aldehyde
Identifiers
CAS Number	139-85-5^Y
3D model (JSmol)	Interactive image
Beilstein Reference	774381
ChEBI	CHEBI:50205
ChEMBL	ChEMBL222021^Y
ChemSpider	8438^Y
DrugBank	DB11268
ECHA InfoCard	100.004.889
EC Number	205-377-7
Gmelin Reference	123001
KEGG	C16700^Y
PubChem CID	8768
UNII	4PVP2HCH4T^Y
CompTox Dashboard (EPA)	DTXSID4074512
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
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Protocatechuic aldehyde

Pharmacological effects

References

See also

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