Ethyl protocatechuate

Ethyl protocatechuate[1]
Names
Preferred 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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.021.391 Edit this at Wikidata
EC Number
  • 223-529-0
UNII
  • InChI=1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3
    Key: KBPUBCVJHFXPOC-UHFFFAOYSA-N
  • CCOC(=O)C1=CC(=C(C=C1)O)O
Properties
C9H10O4
Molar mass 182.175 g·mol−1
Appearance White or pale brownish yellow, crystalline powder; odorless or has a faint

phenol-like odour

Melting point 132 to 135 °C (270 to 275 °F; 405 to 408 K)
Boiling point 357 to 358 °C (675 to 676 °F; 630 to 631 K)[2]
Insoluble in water; soluble in ethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

  1. ^ Ethyl protocatechuate on FAO website[permanent dead link]
  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. S2CID 32329352.
  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.