Protocatechuic aldehyde

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

Protocatechuic aldehyde

Names
IUPAC name 3,4-dihydroxybenzaldehyde
Other names Protocatechualdehyde 3,4-Dihydroxybenzaldehyde Rancinamycin IV 3,4-Dihydroxybenzyl aldehyde
Identifiers
CAS Number	139-85-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL222021^N
ChemSpider	8438^N
ECHA InfoCard	100.004.889
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
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

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]

References

1. Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances. Elvira Conde, Estrella Cadahía, María Concepción García-Vallejo and Brígida Fernández de Simón, J. Agric. Food Chem., 1998, 46 (8), pp 3166–3171 doi:10.1021/jf970863k
2. Biotransformation of protocatechuic aldehyde and caffeic acid to vanillin and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens. Sathuluri Ramachandra Rao and Gokare Aswathanarayana Ravishankar, Journal of Biotechnology, Volume 76, Issues 2-3, 21 January 2000, Pages 137-146 doi:10.1016/S0168-1656(99)00177-7
3. Lee YS, Kang YH, Jung JY, 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.

See also

• Phenolic compounds in wine