:Ethyl protocatechuate
{{chembox
| Watchedfields =
| verifiedrevid =
| ImageFile = Ethyl_protocatechuate.svg
| ImageSize = 200px
| PIN = Ethyl 3,4-dihydroxybenzoate
| OtherNames = Ethyl ester of 3,4-dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid ethyl ester
EDHB
Ethyl-3,4-dihydroxybenzoate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3943-89-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4YGJ96WTBG
| RTECS =
| PubChem = 77547
| ChemSpiderID = 69954
| ChEBI = 132364
| EINECS = 223-529-0
| InChI = 1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3
| InChIKey = KBPUBCVJHFXPOC-UHFFFAOYSA-N
| SMILES = CCOC(=O)C1=CC(=C(C=C1)O)O
}}
|Section2={{Chembox Properties
| C=9|H=10|O=4
| Appearance = White or pale brownish yellow, crystalline powder; odorless or has a faint
phenol-like odour
| Density =
| MeltingPtC = 132 to 135
| MeltingPt_notes =
| BoilingPtC = 357 to 358
| BoilingPt_ref = [http://www.thegoodscentscompany.com/data/rw1244061.html Ethyl protocatechuate on www.thegoodscentscompany.com]
| Solubility = Insoluble in water; soluble in ethanol
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Ethyl protocatechuate is a phenolic compound. It can be found in the peanut seed testa.{{Cite journal | last1 = Huang | first1 = S. C. | last2 = Yen | first2 = G. C. | last3 = Chang | first3 = L. W. | last4 = Yen | first4 = W. J. | last5 = Duh | first5 = P. D. | title = Identification of an Antioxidant, Ethyl Protocatechuate, in Peanut Seed Testa | doi = 10.1021/jf0210019 | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 8 | pages = 2380–2383 | year = 2003 | pmid = 12670184}}{{Cite journal | last1 = Yen | first1 = W. J. | last2 = Chang | first2 = L. W. | last3 = Duh | first3 = P. D. | doi = 10.1016/j.lwt.2004.06.004 | title = Antioxidant activity of peanut seed testa and its antioxidative component, ethyl protocatechuate | journal = LWT - Food Science and Technology | volume = 38 | issue = 3 | pages = 193 | year = 2005 }} It is also present in wine.{{Cite journal | last1 = Baderschneider | first1 = B. | last2 = Winterhalter | first2 = P. | doi = 10.1021/jf010396d | title = Isolation and Characterization of Novel Benzoates, Cinnamates, Flavonoids, and Lignans from Riesling Wine and Screening for Antioxidant Activity | journal = Journal of Agricultural and Food Chemistry | volume = 49 | issue = 6 | pages = 2788–2798 | year = 2001 | pmid = 11409967}} It is the ethylic ester of protocatechuic acid.
The compound is a prolyl 4-hydroxylase inhibitor{{Cite journal | last1 = Wang | first1 = J. | last2 = Buss | first2 = J. L. | last3 = Chen | first3 = G. | last4 = Ponka | first4 = P. | last5 = Pantopoulos | first5 = K. | title = The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells | doi = 10.1016/S0014-5793(02)03389-6 | journal = FEBS Letters | volume = 529 | issue = 2–3 | pages = 309–312 | year = 2002 | pmid = 12372619| s2cid = 32329352 | doi-access = free }} and can be used to protect the myocardium.{{Cite journal
| last1 = Philipp | first1 = S.
| last2 = Cui | first2 = L.
| last3 = Ludolph | first3 = B.
| last4 = Kelm | first4 = M.
| last5 = Schulz | first5 = R.
| last6 = Cohen | first6 = M. V.
| last7 = Downey | first7 = J. M.
| doi = 10.1152/ajpheart.00472.2005
| title = Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS
| journal = AJP: Heart and Circulatory Physiology
| volume = 290
| issue = 1
| pages = H450–H457
| year = 2005
| pmid = 16155105
}}