Ethyl protocatechuate
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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 | |
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ECHA InfoCard | 100.021.391 |
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Properties | |
Chemical formula | 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] |
Solubility in water | 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). Infobox references |
Chemical compound
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
- ^ Ethyl protocatechuate on FAO website[permanent dead link]
- ^ Ethyl protocatechuate on www.thegoodscentscompany.com
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
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Phenolic acids (C6-C1) and their glycosides
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid (2-Hydroxybenzoic acid)
Glycosides |
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Alkylated |
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- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,5-Dihydroxybenzoic acid (Gentisic acid)
- 2,6-Dihydroxybenzoic acid
- 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
- 3,5-Dihydroxybenzoic acid
Alkylated |
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Glycosides | |
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Alkylated |
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