葡萄反应产物
化合物 / 维基百科,自由的 encyclopedia
葡萄反应产物(GRP、GRP1 或 2-S-谷硫酰基咖啡酰酒石酸)[1]是一种酚类化合物,可以解释为什么在加工过程中咖啡酰酒石酸会从葡萄汁中消失。[2]陈年红葡萄酒中也含有这种成分。[3]它由多酚氧化酶酶解产生,对限制葡萄汁的褐变非常重要,[4]特别是在白葡萄酒生产中。 该产品可在模型解决方案中再现。[5][6]
Quick Facts 葡萄反应产物, 识别 ...
葡萄反应产物 | |
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IUPAC名 2-[(E)-3-[3-[2-[(4-amino-4-carboxybutanoyl)amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-4,5-dihydroxyphenyl]prop-2-enoyl]oxy-3-hydroxybutanedioic acid | |
别名 | GRP GRP1 2-S-Glutathionyl caftaric acid 2-S-谷胱酰基咖啡酰酒石酸 |
识别 | |
CAS号 | |
PubChem | 71308212 |
SMILES |
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ChEBI | 147433 |
性质 | |
化学式 | C23H27N3O15S |
摩尔质量 | 617.54 g·mol−1 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
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通过质谱法可以确定其在葡萄酒中的浓度。[7]S-谷胱酰基咖啡酰酒石酸本身能被氧化。[8] 它不是葡萄多酚氧化酶的底物,但灰葡萄孢菌的漆酶可以利用它形成 GRP2。[9]
相关分子
其他相关分子是“反式”-咖啡酰酒石酸衍生物,如 GRP1,2-苯醌[10]和 2,5-di-S-谷氨酰基咖啡酰酒石酸盐(GRP2)[11]或与花青素的加合物。[12]
参考文献
- Veronique F. Cheynier; Eugene K. Trousdale; Vernon L. Singleton; Michel J. Salgues; Renee Wylde. Characterization of 2-S-glutathionyl caftaric acid and its hydrolysis in relation to grape wines. J. Agric. Food Chem. 1986, 34 (2): 217–221. doi:10.1021/jf00068a016.
- Anis Arnous; Dimitris P. Makris; Panagiotis Kefalas. Effect of Principal Polyphenolic Components in Relation to Antioxidant Characteristics of Aged Red Wines. J. Agric. Food Chem. 2001, 49 (12): 5736–5742. PMID 11743756. doi:10.1021/jf010827s.
- V.L. Singleton; M. Salgues; J. Zaya; E. Trousdale. Caftaric Acid Disappearance and Conversion to Products of Enzymic Oxidation in Grape Must and Wine (PDF). Am. J. Enol. Vitic. 1985, 36 (1): 50.
- V. Cheynier; C. Owe; J. Rigaud. Oxidation of Grape Juice Phenolic Compounds in Model Solutions. Journal of Food Science. 1988, 53 (6): 1729–1732. doi:10.1111/j.1365-2621.1988.tb07828.x.
- Veronique Cheynier; Jorge M. Ricardo da Silva. Oxidation of grape procyanidins in model solutions containing trans-caffeoyltartaric acid and polyphenol oxidase. J. Agric. Food Chem. 1991, 39 (6): 1047–1049. doi:10.1021/jf00006a008.
- Straightforward Method To Quantify GSH, GSSG, GRP, and Hydroxycinnamic Acids in Wines by UPLC-MRM-MS. Anna Vallverdú-Queralt, Arnaud Verbaere, Emmanuelle Meudec, Veronique Cheynier and Nicolas Sommerer, J. Agric. Food Chem. 2015, 63, 142−149, doi:10.1021/jf504383g
- Salgues, M.; Cheynier, V.; Gunata, Z.; Wylde, R. Oxidation of Grape Juice 2-S-Glutathionyl Caffeoyl Tartaric Acid by Botrytis cinerea Laccase and Characterization of a New Substance: 2,5-di-S-Glutathionyl Caffeoyl Tartaric Acid. Journal of Food Science. 1986, 51 (5): 1191. doi:10.1111/j.1365-2621.1986.tb13081.x.
- Cheynier V.; Rigaud J.; Souquet J.-M.; Duprat F.; Moutounet M. Must browning in relation to the behavior of phenolic compounds during oxidation. American Journal of Enology and Viticulture. 1990, 41 (4): 346–349.INIST(法语:Institut de l'information scientifique et technique):5402970
- Véronique Cheynier; Jacques Rigaud; Michel Moutounet. Oxidation kinetics of trans-caffeoyltartrate and its glutathione derivatives in grape musts. Phytochemistry. 1990, 29 (6): 1751–1753. doi:10.1016/0031-9422(90)85008-4.
- Petros Kneknopoulos; George K. Skouroumounis; Yoji Hayasaka; Dennis K. Taylor. New Phenolic Grape Skin Products from Vitis vinifera cv. Pinot Noir. J. Agric. Food Chem. 2011, 59 (3): 1005–1011. PMID 21214245. doi:10.1021/jf103682x.