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;
EC Number	205-377-7;
Gmelin Reference	123001
KEGG	C16700 ;
PubChem CID	8768;
UNII	4PVP2HCH4T ;
	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

↑ "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.
↑ "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.
↑ "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.
↑ "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. Bibcode: 2014PLoSO...9k3242K.

Protocatechuic aldehyde

Topic: Chemistry

Pharmacological effects

References

See also

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
EC Number	205-377-7
Gmelin Reference	123001
KEGG	C16700^Y
PubChem CID	8768
UNII	4PVP2HCH4T^Y
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