綠原酸

綠原酸; Chlorogenic acid
	IUPAC名; (1S,3R,4R,5R)-3[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy1,4,5-trihydroxycyclohexanecarboxylic acid
别名	3-(3,4-Dihydroxycinnamoyl)quinate; 3-(3,4-Dihydroxycinnamoyl)quinic acid; 3-Caffeoylquinate; 3-Caffeoylquinic acid; 3-CQA; 3-O-Caffeoylquinic acid; Chlorogenate; Chlorogenic acid; Heriguard; 3-trans-Caffeoylquinic acid
识别
CAS号	327-97-9
PubChem	1794427
ChemSpider	1405788
SMILES	O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2;
InChI	1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1;
InChIKey	CWVRJTMFETXNAD-JUHZACGLBD
ChEBI	16112
RTECS	GU8480000
性质
化学式	C16H18O9
摩尔质量	354.31 g·mol−1
密度	1.28 g/cm3
熔点	207-209 °C（271 K）
危险性
警示术语	R：-
安全术语	S：S24 S25 S28 S37 S45
NFPA 704	0 1 0
	若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。

綠原酸（Chlorogenic acid；CGA），又名氯吉酸、氯原酸、咖啡单宁酸、杜仲绿原酸、全蝎提取物、咖啡酰奎尼酸等^[1]，是一天然的化合物，由咖啡酸及(−)-奎尼酸酯化而成。綠原酸是一種重要的生物合成中間體^[2]。綠原酸是木質素（lignin）的生物合成的重要中間生成物。綠原素作為一種抗氧化劑，可令餐後葡萄醣釋出進入血液的過程減慢^[3]。

綠原酸這個名詞也泛指羥基肉桂酸（即：咖啡酸、阿魏酸及对香豆酸）與奎尼酸的酯化物^[4]。

结构与性质[编辑]

綠原酸是咖啡酸與L-奎尼酸和3號位羥基縮合形成的酯。^[5]綠原酸的異構體包括奎尼酸其它位置羥基酯化的產物，如4-O-咖啡酰奎尼酸（cryptochlorogenic acid或簡稱4-CQA）和5-O-咖啡酰奎尼酸（neochlorogenic acid或稱5-CQA，新綠原酸）。一位羥基的異構體尚未在自然界中發現。^[4]

兩個羥基被酯化則稱異綠原酸（isochlorogenic acid），存在於咖啡中。^[6]例如3,4-二咖啡酰奎尼酸和3,5-二咖啡酰奎尼酸。^[7] 和1,5-二咖啡酰奎尼酸。

綠原酸的紫外-可见光谱，最大吸收峰位于325nm

綠原酸可溶于乙醇和丙酮。

自然来源[编辑]

綠原酸存在于毛竹（Phyllostachys edulis）^[8]以及其它植物中^[9]，也是桃中常见的酚类化合物^[10]。

綠原酸也在健康的帚石楠（Calluna vulgaris）嫩芽中发现^[11]。

綠原酸是金銀花的主要抗菌、抗病毒有效藥理成分之一。^[12]

參考文獻[编辑]

^ 绿原酸 CAS: 327-97-9. 2016-08-05 [2016-08-07]. （原始内容存档于2016-08-14）（中文（简体）‎）.
^ Boerjan, Wout; Ralph, John; Baucher, Marie. Lignin biosynthesis. Annu. Rev. Plant Biol. 2003, 54: 519–46. PMID 14503002. doi:10.1146/annurev.arplant.54.031902.134938.
^ Johnston, K. L.; Clifford, M. N.; Morgan, L. M. Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. Am. J. Clin. Nutrit.（英语：The American Journal of Clinical Nutrition）. 2003-10, 78 (4): 728–733 [2016-08-07]. PMID 14522730. （原始内容存档于2010-04-21）（英语）.
^ ^4.0 ^4.1 Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. Hierarchical Scheme for LC-MSⁿ Identification of Chlorogenic Acids. Journal of Agricultural and Food Chemistry. 2003, 51 (10): 2900–2911. PMID 12720369. doi:10.1021/jf026187q.
^ Clifford, M. N. Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden. J. Sci. Food Agr. 1999, 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
^ Isochlorogenic Acid. Isolation from Coffee and Structure Studies. H. M. Barnes, J. R. Feldman and W. V. White, J. Am. Chem. Soc., 1950, volume 72, issue 9, pages 4178–4182, doi:10.1021/ja01165a095
^ Corse, J.; Lundin, R. E.; Waiss, A. C. Identification of several components of isochlorogenic acid. Phytochem. May 1965, 4 (3): 527–529. doi:10.1016/S0031-9422(00)86209-3.
^ Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin. Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis). Journal of Agricultural and Food Chemistry. 2001, 49 (20): 4646–46552. doi:10.1021/jf010514x.
^ Clifford, M. N. 14. The analysis and characterization of chlorogenic acids and other cinnamates. C. Santos-Buelga & G. Williamson (Eds.) (编). Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. 2003: 314–337. ISBN 0-85404-580-5.
^ Cheng, G. W.; Crisosto, C. H. Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue (PDF). J. Amer. Soc. Hort. Sci. September 1995, 120 (5): 835–838 [2016-08-07]. （原始内容 (PDF)存档于2014-05-14）.
^ Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. Phenolic composition and its seasonal variation in Calluna vulgaris. Phytochem. 1982, 21 (6): 1397–1401. doi:10.1016/0031-9422(82)80150-7.
^ Ding, Yue; Cai, Zeyu. Antiviral activity of chlorogenic acid against influenza A (H1N1/H3N2) virus and its inhibition of neuraminidase. Scientific Reports. 2017, 7: 45723. PMC 5385491. PMID 28393840. doi:10.1038/srep45723.

[1] 绿原酸 CAS: 327-97-9. 2016-08-05 [2016-08-07]. （原始内容存档于2016-08-14）（中文（简体）‎）.

[2] Boerjan, Wout; Ralph, John; Baucher, Marie. Lignin biosynthesis. Annu. Rev. Plant Biol. 2003, 54: 519–46. PMID 14503002. doi:10.1146/annurev.arplant.54.031902.134938.

[3] Johnston, K. L.; Clifford, M. N.; Morgan, L. M. Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. Am. J. Clin. Nutrit.（英语：The American Journal of Clinical Nutrition）. 2003-10, 78 (4): 728–733 [2016-08-07]. PMID 14522730. （原始内容存档于2010-04-21）（英语）.

[hierarchical-4] 4.0 ^4.1 Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. Hierarchical Scheme for LC-MSⁿ Identification of Chlorogenic Acids. Journal of Agricultural and Food Chemistry. 2003, 51 (10): 2900–2911. PMID 12720369. doi:10.1021/jf026187q.

[5] Clifford, M. N. Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden. J. Sci. Food Agr. 1999, 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.

[6] Isochlorogenic Acid. Isolation from Coffee and Structure Studies. H. M. Barnes, J. R. Feldman and W. V. White, J. Am. Chem. Soc., 1950, volume 72, issue 9, pages 4178–4182, doi:10.1021/ja01165a095

[7] Corse, J.; Lundin, R. E.; Waiss, A. C. Identification of several components of isochlorogenic acid. Phytochem. May 1965, 4 (3): 527–529. doi:10.1016/S0031-9422(00)86209-3.

[8] Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin. Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis). Journal of Agricultural and Food Chemistry. 2001, 49 (20): 4646–46552. doi:10.1021/jf010514x.

[9] Clifford, M. N. 14. The analysis and characterization of chlorogenic acids and other cinnamates. C. Santos-Buelga & G. Williamson (Eds.) (编). Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. 2003: 314–337. ISBN 0-85404-580-5.

[10] Cheng, G. W.; Crisosto, C. H. Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue (PDF). J. Amer. Soc. Hort. Sci. September 1995, 120 (5): 835–838 [2016-08-07]. （原始内容 (PDF)存档于2014-05-14）.

[11] Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. Phenolic composition and its seasonal variation in Calluna vulgaris. Phytochem. 1982, 21 (6): 1397–1401. doi:10.1016/0031-9422(82)80150-7.

[12] Ding, Yue; Cai, Zeyu. Antiviral activity of chlorogenic acid against influenza A (H1N1/H3N2) virus and its inhibition of neuraminidase. Scientific Reports. 2017, 7: 45723. PMC 5385491. PMID 28393840. doi:10.1038/srep45723.

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綠原酸

结构与性质[编辑]

自然来源[编辑]

參考文獻[编辑]

导航菜单

搜索

綠原酸 Chlorogenic acid

IUPAC名 (1S,3R,4R,5R)-3[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy1,4,5-trihydroxycyclohexanecarboxylic acid
别名	3-(3,4-Dihydroxycinnamoyl)quinate 3-(3,4-Dihydroxycinnamoyl)quinic acid 3-Caffeoylquinate 3-Caffeoylquinic acid 3-CQA 3-O-Caffeoylquinic acid Chlorogenate Chlorogenic acid Heriguard 3-trans-Caffeoylquinic acid
识别
CAS号	327-97-9
PubChem	1794427
ChemSpider	1405788
SMILES	O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
InChI	1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChIKey	CWVRJTMFETXNAD-JUHZACGLBD
ChEBI	16112
RTECS	GU8480000
性质
化学式	C₁₆H₁₈O₉
摩尔质量	354.31 g·mol⁻¹
密度	1.28 g/cm³
熔点	207-209 °C（271 K）
危险性
警示术语	R：-
安全术语	S：S24 S25 S28 S37 S45
NFPA 704	0 1 0
若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。