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原兒茶酸乙酯

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原兒茶酸乙酯[1]
IUPAC名
Ethyl 3,4-dihydroxybenzoate
別名 3,4-二羥基苯甲酸乙酯
EDHB
識別
CAS號 3943-89-3  checkY
PubChem 77547
ChemSpider 69954
SMILES
 
  • CCOC(=O)C1=CC(=C(C=C1)O)O
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
EINECS 223-529-0
ChEBI 132364
性質
化學式 C9H10O4
摩爾質量 182.17 g·mol−1
外觀 白色或淡棕黃色晶體
氣味 無臭或微弱的苯酚氣味
熔點 132-135 °C(405-408 K)
沸點 357-358 °C(630-631 K)([2]
溶解性 不溶於水,可溶於乙醇
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

原兒茶酸乙酯(英語:Ethyl protocatechuate)是原兒茶酸乙醇形成的,分子式C9H10O4,可在花生種皮中發現[3][4],在葡萄酒中也有發現[5]

原兒茶酸乙酯也是脯氨酸-4-羥化酶英語prolyl 4-hydroxylase抑制劑[6],可用於保護心肌[7]

參考文獻

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