Ethyl protocatechuate

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Ethyl protocatechuate[1]
IUPAC name

Ethyl 3,4-dihydroxybenzoate

Other names

Ethyl ester of 3,4- dihydroxybenzoic acid
3,4-dihydroxybenzoic acid ethyl ester
EDHB
Ethyl-3,4-dihydroxybenzoate

Identifiers
CAS number 3943-89-3
PubChem 77547
ChemSpider 69954
EC number 223-529-0
Jmol-3D images Image 1
Properties
Molecular formula C9H10O4
Molar mass 182.17 g/mol
Appearance White or pale brownish yellow, crystalline powder; odourless or has a faint

phenol-like odour

Melting point 132-135°C
Boiling point 357-358°C[2]
Solubility in water Insoluble in water; soluble in ethanol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethyl protocatechuate is a phenolic compound. It can be found in the peanut seed testa.[3][4] It is also present in wine.[5] It is the ethylic ester of protocatechuic acid.

The compound is a prolyl 4-hydroxylase inhibitor[6] and can be used to protect the myocardium.[7]

See also

References

  1. ↑ Ethyl protocatechuate on FAO website
  2. ↑ Ethyl protocatechuate on www.thegoodscentscompany.com
  3. ↑ Huang, S. C.; Yen, G. C.; Chang, L. W.; Yen, W. J.; Duh, P. D. (2003). "Identification of an Antioxidant, Ethyl Protocatechuate, in Peanut Seed Testa". Journal of Agricultural and Food Chemistry 51 (8): 2380–2383. doi:10.1021/jf0210019. PMID 12670184. 
  4. ↑ Yen, W. J.; Chang, L. W.; Duh, P. D. (2005). "Antioxidant activity of peanut seed testa and its antioxidative component, ethyl protocatechuate". LWT - Food Science and Technology 38 (3): 193. doi:10.1016/j.lwt.2004.06.004. 
  5. ↑ Baderschneider, B.; Winterhalter, P. (2001). "Isolation and Characterization of Novel Benzoates, Cinnamates, Flavonoids, and Lignans from Riesling Wine and Screening for Antioxidant Activity". Journal of Agricultural and Food Chemistry 49 (6): 2788–2798. doi:10.1021/jf010396d. PMID 11409967. 
  6. ↑ Wang, J.; Buss, J. L.; Chen, G.; Ponka, P.; Pantopoulos, K. (2002). "The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells". FEBS Letters 529 (2–3): 309–312. doi:10.1016/S0014-5793(02)03389-6. PMID 12372619. 
  7. ↑ Philipp, S.; Cui, L.; Ludolph, B.; Kelm, M.; Schulz, R.; Cohen, M. V.; Downey, J. M. (2005). "Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS". AJP: Heart and Circulatory Physiology 290 (1): H450–H457. doi:10.1152/ajpheart.00472.2005. PMID 16155105. 
Phenolic acids and their glycosides
Monohydroxybenzoic acids
Aglycones
Glycosides
  • p-Hydroxybenzoic acid glucoside
Dihydroxybenzoic acids
Trihydroxybenzoic acids
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