綠原酸
| 綠原酸 Chlorogenic acid |
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|---|---|
 |
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| IUPAC名 (1S,3R,4R,5R)-3[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy1,4,5-trihydroxycyclohexanecarboxylic acid |
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| 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 |
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| InChI |
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| 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
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| 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
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]。
參考文獻[编辑]
- ^ 绿原酸 CAS: 327-97-9. 2016-08-05 （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.. 2003-10, 78 (4): 728–733. PMID 14522730 （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. (编) C. Santos-Buelga & G. Williamson (Eds.). 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.
- ^ 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.
