二咖啡醯酒石酸

二咖啡醯酒石酸
	IUPAC名; (2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
別名	Cichoric acid; (2R,3R)-O-Dicaffeoyltartaric acid
識別
CAS號	6537-80-0
PubChem	5281764
ChemSpider	4445078
SMILES	O=C(O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O;
InChI	1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1;
InChIKey	YDDGKXBLOXEEMN-IABMMNSOBV
KEGG	C10437
性質
化學式	C22H18O12
莫耳質量	474.371 g/mol g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二咖啡醯酒石酸（英語：(2R,3R)-O-Dicaffeoyltartaric acid）菊苣酸（英語：Chicoric acid）又稱西可酸（英語：Cichoric acid），是一種羥基肉桂酸，屬於苯基丙酮類有機化合物，存在於多種植物物種中。它是咖啡酸和酒石酸的衍生物。^[1]

作為區分紫錐菊（Echinacea purpurea）物種的合適標記，它通常使用RP-HPLC和薄層色譜（TLC）方法進行檢測。^[2]

來源

菊苣酸最早是從菊苣（Cichorium intybus）中分離出來的，但也大量存在於紫錐菊中，特別是紫錐菊、蒲公英葉、羅勒、檸檬香草和水生植物，包括藻類和海草。^[3]^[4]^[5]^[6]

生物學功能

在體外和體內研究中，菊苣酸都被證明可以刺激吞噬細胞，抑制透明質酸酶（一種在人體內分解透明質酸的酶）的功能，保護膠原蛋白免受自由基的損害，以及抑制HIV-1整合酶的功能。^[7]^[8]

參見

咖啡醯酒石酸

參考文獻

^ John Shi; Giuseppe Mazza; Marc Le Maguer. Functional Foods: Biochemical and Processing Aspects. CRC Press. 27 February 2002: 241–. ISBN 978-1-4200-1287-3.
^ Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in WHO Monographs on Selected Medicinal Plants - Volume 1
^ Chkhikvishvili, I. D.; Kharebava, G. I. Chicoric and Chlorogenic Acids in Plant Species from Georgia. Applied Biochemistry and Microbiology. 2001, 37 (2): 188–191. S2CID 6322156. doi:10.1023/a:1002888016985.
^ Lee, Jungmin. Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products. Journal of Functional Foods. 2010, 2 (2): 158–162. doi:10.1016/j.jff.2010.02.003.
^ Lee, Jungmin; Scagel, Carolyn F. Chicoric acid found in basil (Ocimum basilicum L.) leaves. Food Chemistry. 2009, 115 (2): 650–656. doi:10.1016/j.foodchem.2008.12.075.
^ Lee, Jungmin; Scagel, Carolyn F. Chicoric acid: Chemistry, distribution, and production. Frontiers in Chemistry. 2013, 1: 40. Bibcode:2013FrCh....1...40L. PMC 3982519  . PMID 24790967. doi:10.3389/fchem.2013.00040  .
^ Mazza, G.; Oomah, B. Dave, Herbs, Botanicals & Teas, CRC Press: 51, 2000 [2008-12-09], ISBN 1-56676-851-9
^ Miller, Sandra Carol; Yu, He-Ci, Echinacea, CRC Press: 140, 2004 [2008-12-09], ISBN 0-415-28828-2

[func-1] John Shi; Giuseppe Mazza; Marc Le Maguer. Functional Foods: Biochemical and Processing Aspects. CRC Press. 27 February 2002: 241–. ISBN 978-1-4200-1287-3.

[2] Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in WHO Monographs on Selected Medicinal Plants - Volume 1

[3] Chkhikvishvili, I. D.; Kharebava, G. I. Chicoric and Chlorogenic Acids in Plant Species from Georgia. Applied Biochemistry and Microbiology. 2001, 37 (2): 188–191. S2CID 6322156. doi:10.1023/a:1002888016985.

[4] Lee, Jungmin. Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products. Journal of Functional Foods. 2010, 2 (2): 158–162. doi:10.1016/j.jff.2010.02.003.

[5] Lee, Jungmin; Scagel, Carolyn F. Chicoric acid found in basil (Ocimum basilicum L.) leaves. Food Chemistry. 2009, 115 (2): 650–656. doi:10.1016/j.foodchem.2008.12.075.

[6] Lee, Jungmin; Scagel, Carolyn F. Chicoric acid: Chemistry, distribution, and production. Frontiers in Chemistry. 2013, 1: 40. Bibcode:2013FrCh....1...40L. PMC 3982519  . PMID 24790967. doi:10.3389/fchem.2013.00040  .

[herb-7] Mazza, G.; Oomah, B. Dave, Herbs, Botanicals & Teas, CRC Press: 51, 2000 [2008-12-09], ISBN 1-56676-851-9

[ech-8] Miller, Sandra Carol; Yu, He-Ci, Echinacea, CRC Press: 140, 2004 [2008-12-09], ISBN 0-415-28828-2

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二咖啡醯酒石酸


IUPAC名 (2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
別名	Cichoric acid; (2R,3R)-O-Dicaffeoyltartaric acid
識別
CAS號	6537-80-0 ^Y
PubChem	5281764
ChemSpider	4445078
SMILES	O=C(O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O
InChI	1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
InChIKey	YDDGKXBLOXEEMN-IABMMNSOBV
KEGG	C10437
性質
化學式	C₂₂H₁₈O₁₂
莫耳質量	474.371 g/mol g·mol⁻¹
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。