Protocatechuic aldehyde

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

Tracking categories (test):

* SizeSet

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

1. ↑ "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.
2. ↑ "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.
3. ↑ "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.
4. ↑ "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.

## See also

* Phenolic compounds in wine

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*[CID]: Compound ID