中文名 | 谷胱甘肽 |
英文名 | Glutathione |
别名 | 谷胱甘肽 谷光甘肽 L-谷胱甘肽 L-谷胱苷肽 还原型谷胱苷肽 还原型谷胱甘肽 谷胱甘肽(GSH) 谷胱甘肽(还原型) 谷胱甘肽(GSSG) 谷胱甘肽(还原性谷胱甘肽) Γ-谷氨酰-半胱氨酰-甘氨酸 5-L-谷氨酰-L-半胱氨酰甘氨酸 GLUTATHIONE REDUCED 还原型谷胱甘肽 |
英文别名 | GSH glutide glutinal isethion glutatiol glutatione Glutathion Glutathione l-glutatione L-Glutathione ReducedGlutathione Antisense compounds Glutathione reduced Glutathione, reduced gamma-glutamylcysteinylglycine 5-l-glutamyl-l-cysteinylglycine Glutathione, Reduced, Free Acid gamma-L-Glutamyl-L-cysteinylglycine L-gamma-glutamyl-L-cysteinylglycine n-(n-l-gamma-glutamyl-l-cysteinyl)-glycin L-gamma-glutamyl-3-sulfido-L-alanylglycine N(N-L-.gamma.-Glutamyl-L-cysteinyl)glycine {[N-(2-ammonio-4-carboxybutanoyl)cysteinyl]amino}acetate |
CAS | 70-18-8 |
EINECS | 200-725-4 |
化学式 | C10H17N3O6S |
分子量 | 307.32 |
InChI | InChI=1/C10H17N3O6S/c11-5(1-2-7(14)15)9(18)13-6(4-20)10(19)12-3-8(16)17/h5-6,20H,1-4,11H2,(H,12,19)(H,13,18)(H,14,15)(H,16,17) |
InChIKey | RWSXRVCMGQZWBV-WDSKDSINSA-N |
密度 | 1.4482 (rough estimate) |
熔点 | 192-195 °C (dec.) (lit.) |
沸点 | 754.5±60.0 °C(Predicted) |
比旋光度 | -16.5 º (c=2, H2O) |
闪点 | 411.272°C |
水溶性 | soluble |
蒸汽压 | 0mmHg at 25°C |
溶解度 | H2O: 50 mg/mL |
折射率 | -17 ° (C=2, H2O) |
酸度系数 | pK1 2.12; pK2 3.53; pK3 8.66; pK4 9.12(at 25℃) |
PH值 | 3 (10g/l, H2O, 20°C) |
存储条件 | 2-8°C |
稳定性 | 稳定。与强氧化剂不相容。 |
敏感性 | Sensitive to air |
外观 | 粉末 |
颜色 | White |
气味 | Odorless |
Merck | 14,4475 |
BRN | 1729812 |
物化性质 | 谷胱甘肽的分子量为307.33,熔点189~193℃ (分解),晶体呈无色透明细长柱状,等电点为5.93。它溶于水、稀醇、液氨和甲基甲酰胺,而不溶于醇、醚和丙酮。生物体内只有GSH才具有生理活性,而GSSG需还原后才能发挥其重要的生理功能。GSH在高水分活性下不易保存,只有将水分活性控制在0.3以下才能够长期稳定保存。有研究显示,在含有GSH的维生素C水溶液(pH3.3)中,由于有维生素C的强还原作用,溶液中的GSH不会氧化为GSSG,但其分解速度却加快;而存在于维生素C水溶液中的GSSG也不会转变为GSH,且保存稳定性很好。并且经口摄入的GSSG在小肠上部可被还原为GSH,在小肠上皮细胞表面经γ-GTP(将GSH分解为谷氨酸与Cys-Gly)及二肽酶的作用而被吸收,同样可以发挥其重要的生理功能。 谷胱甘肽广泛存在于动、植物中,在面包酵母、小麦胚芽和动物肝脏中的含量极高,达100~1000mg/100g;在人和动物的血液中含量也较丰富,如人血液中含26~34mg/100g、鸡血中含58~73mg/100g、猪血中含10~15mg/100g、狗血中含14~22mg/100g。许多蔬菜、薯类和谷物中也含有GSH (见表1)。 以上信息由彤彤编辑整理。 |
MDL号 | MFCD00065939 |
危险品标志 | Xi - 刺激性物品 |
风险术语 | R68 - 可能有不可逆后果的危险。 R36/37/38 - 刺激眼睛、呼吸系统和皮肤。 |
安全术语 | S24/25 - 避免与皮肤和眼睛接触。 S36/37/39 - 穿戴适当的防护服、手套和护目镜或面具。 S27 - 一旦衣物受到污染,请立即脱去。 S26 - 不慎与眼睛接触后,请立即用大量清水冲洗并征求医生意见。 |
WGK Germany | 2 |
RTECS | MC0556000 |
FLUKA BRAND F CODES | 9-23 |
TSCA | Yes |
海关编号 | 29309070 |
上游原料 | 维生素 C 硫化氢 |
下游产品 | 前列腺素E1 4,4'-二羧基二苯二硫醚 AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE |
参考资料 展开查看 | 1. 席高磊 许克静 王宏伟 等. 4-甲基-7-羟基香豆素及其衍生物的抗氧化性能[J]. 精细化工 2019(6). 2. 余丽丽 尤静 梁飞 等. GSH、pH及温度多重敏感型微凝胶的合成及性能[J]. 高分子材料科学与工程 2015 31(010):22-26. 3. 余丽丽 穆瑞花 尤静 等. pH-GSH双敏感型P(mPEGMA-DEAM-SS)水凝胶的溶胀动力学[J]. 高分子材料科学与工程 2015 31(005):19-24. 4. 余丽丽 姚琳 苏力 丁淑梅 田洪玉.pH、GSH双敏感型胶束的制备及其载药性能研究[J].化工科技 2016 24(04):5-9. 5. 余敏 黄晶晶 马敏 付瑞燕 鄢嫣 张福生 殷俊峰 谢宁宁.三肽的锌螯合活性及定量构效关系分析[J].高等学校化学学报 2018 39(02):234-240. 6. 张金堂 沙迪 夏广军 徐红艳.东北山核桃壳黄酮对小鼠氧化损伤的防御作用[J].食品科学 2018 39(05):252-257. 7. 杨雪莉 彭丽媛 李栋 曹敏 同婉莹 王芮 王旭臻 余丽丽.介孔二氧化硅-壳聚糖复合粒子的合成[J].化工科技 2019 27(04):22-26. 8. 魏光强 李华瑞 赵存朝 等. 发酵牦牛乳蛋白肽的分离纯化及抗氧化活性研究[J]. 中国奶牛 2020 000(004):32-38. 9. 张晓平 陈芝飞 韩路 赵学斌 武志勇 赵阔 牛洋洋 赵铭钦 席高磊.吡嗪-唑联芳化合物的合成及其抗氧化性能[J].精细化工 2020 37(07):1461-1468. 10. 余丽丽 姚琳 尤静 等. 含二硫键铵盐交联水凝胶的制备及其性能研究[J]. 功能材料 2015 000(006):6134-6138. 11. 席高磊 陈芝飞 杨金初 等. 咪唑并[1 2-a]吡啶化合物的无溶剂合成及其抗氧化性能[J]. 合成化学 2020 028(003):194-201. 12. 柏昌旺 章超桦 林海生 秦小明 曹文红 杨雨柔.响应面法优化制备牡蛎短肽工艺[J].广东海洋大学学报 2019 39(06):85-92. 13. 李丽, 阮金兰, 钱伟亮,等. 多指标评价核桃蛋白及多肽的抗氧化活性[J]. 食品研究与开发, 2017, 038(003):1-4. 14. 梁晓芳, 牟建楼, 严超,等. 扇贝酶解条件的优化及其抗氧化性的研究[J]. 中国调味品, 2018(1):61-66. 15. 赵稷,高金波,侯丽然,李国清,楚婧,侯巍.木犀草素-Cr(Ⅲ)配合物对α-葡萄糖苷酶抑制作用的研究[J].微量元素与健康研究,2013,30(06):5-7. 16. 滕杨, 罗时旋, 侯丽然,等. 木犀草素-锌(Ⅱ)配合物的合成及对α-葡糖苷酶活性的抑制作用研究[J]. 中国药房, 2015, 026(016):2172-2175. 17. 严超, 牟建楼, 陈志周,等. 栉孔扇贝酶解液制备条件优化及其抗氧化性研究[J]. 中国调味品, 2017(12):1-6. 18. 钟新, 李军生, 阎柳娟,等. 氧化变构制备大豆分离蛋白质基表面活性剂[J]. 中国饲料, 2017, 000(020):23-27,35. 19. 朱培, 钟海雁, 黄卫文,等. 用薄层扫描法测定油茶粕蛋白水解物的多肽[J]. 经济林研究, 2013(02):142-145. 20. 孔晓雪, 李蕴涵, 李柚,等. 葡萄糖氧化酶和谷氨酰胺转氨酶对发酵麦麸面团加工品质的影响[J]. 食品工业科技, 2019, 40(9). 21. 谢忠萍, 程国虎. 谷胱甘肽对兔精液获能作用及获能相关基因表达的影响[J]. 当代畜牧, 2016, 000(006):27-29. 22. 张菲, 陈文欣, 张俊华,等. 铜纳米簇荧光探针高灵敏定量检测谷丙转氨酶[J]. 吉林师范大学学报(自然科学版), 2020(1). 23. 黄晶晶, 余敏, 马敏,等. 锌螯合肽的两端排序法定量构效关系[J]. 食品科学, 2018, 39(21):18-24. 24. 万玉萍, 周小华, 冯琳,等. 谷胱甘肽-铬-烟酸螯合物的制备与表征[J]. 氨基酸和生物资源, 2015, 37(1):49-55. 25. 高静, 王楠, 关思静,等. 白僵菌诱导甘草气孔关闭的信号机制研究[J]. 陕西农业科学, 2019, 065(005):72-75. 26. 杜博玮, 徐晓冰, 郭尚伟,等. 高抗氧化性小分子阿胶的研究[J]. 北京化工大学学报:自然科学版, 2019, 46(6):15-20. 27. 孙雯, 李莎, 杨飞燕,等. 自制多脏器保存液对低温大鼠睾丸氧自由基表达的影响[J]. 中华男科学杂志, 2011, 17(007):655-657. 28. 孙雯, 张金萍, 揭芳,等. 自制多脏器保存液对大鼠睾丸一氧化氮合酶的影响[J]. 中国组织工程研究, 2011, 15(031):5813-5816. 29. 王露佳, 孙雯, 张金萍,等. 自制移植肝低温保存液对氧自由基的影响[J]. 中国组织工程研究, 2013, 000(005):837-842. 30. 邓张双,黄蓉,刘秀继,李知洪,姚鹃,李啸,杜维力,邹坤,龚大春.酵母产还原型谷胱甘肽制备过程中的稳定性研究[J].三峡大学学报(自然科学版),2020,42(06):97-102. 31. 葛正凯,黄倩,李洁,郑晓春,王斌,史学伟.不同抗氧化剂对白葡萄酒品质的影响[J].中国酿造,2020,39(10):136-144. 32. 张柳婷,吕金月,张港,李亚涛,蔡梅红,段玉清.芡种壳多酚超声辅助提取工艺优化及其对金黄色葡萄球菌的抑制效果[J].南方农业学报,2021,52(01):189-197. 33. 念,邓媛元,魏振承,张雁,唐小俊,李萍,周鹏飞,刘光,张名位.重组小麦静息巯基氧化酶的表达、酶学特性及其对面包品质的影响[J].生物工程学报,2021,37(02):593-603. 34. Jiang, Tingting, et al. "Bergaptol, a mechanism-based inactivator of CYP2C9." Medicinal Chemistry Research 29 (2020): 1230-1237.https://doi.org/10.1007/s00044-020-02564-x 35. Lihua Chen, Shiyi Zhao, Mingchao Liu, Peng Wu, Chuangfu Chen,A novel label-free electrochemical immunosensor modified by glutathione and hyaluronic acid for the ultrasensitive and ultraselective detection of brucellosis in dilute serum,Sensors and Actuat 36. Qing Pei, Xiuli Hu, Shi Liu, Yang Li, Zhigang Xie, Xiabin Jing, Paclitaxel dimers assembling nanomedicines for treatment of cervix carcinoma, Journal of Controlled Release, Volume 254, 2017, Pages 23-33, ISSN 0168-3659, https://doi.org/10.1016/j.jconrel.20 37. Ma, Guoqing, et al. "Dual-responsive polyphosphoester-doxorubicin prodrug containing a diselenide bond: synthesis, characterization, and drug delivery." ACS Biomaterials Science & Engineering 4.7 (2018): 2443-2452.https://doi.org/10.1021/acsbiomaterials.8b 38. Li, Meixiu, et al. "Direct generation of Ag nanoclusters on reduced graphene oxide nanosheets for efficient catalysis, antibacteria and photothermal anticancer applications." Journal of colloid and interface science 529 (2018): 444-451.https://doi.org/10.1 39. Xin Wang, Wenhai Lin, Wei Zhang, Cheng Li, Tingting Sun, Guang Chen, Zhigang Xie,Amphiphilic redox-sensitive NIR BODIPY nanoparticles for dual-mode imaging and photothermal therapy,Journal of Colloid and Interface Science,Volume 536,2019,Pages 208-214 40. Song, Zhongqian, et al. "A novel method to decorate Au clusters onto graphene via a mild co-reduction process for ultrahigh catalytic activity." Journal of materials chemistry A 5.1 (2017): 230-239.DOI: 10.1039/C6TA08284J 41. Wu, T., Li, L., Song, G. et al. An ultrasensitive electrochemical sensor based on cotton carbon fiber composites for the determination of superoxide anion release from cells. Microchim Acta 186, 198 (2019). https://doi.org/10.1007/s00604-019-3304-1 42. Niu, Meng, et al. "Inhibitory effects of ultrasound combined with ascorbic acid or glutathione on enzymatic darkening of whole-wheat raw noodles." LWT-Food Science and Technology 59.2 (2014): 901-907.https://doi.org/10.1016/j.lwt.2014.06.056 43. Zhang, Fangmei, et al. "Enzymatic determination of uric acid using water-soluble CuInS/ZnS quantum dots as a fluorescent probe." Microchimica Acta 185.11 (2018): 1-8.https://doi.org/10.1007/s00604-018-3030-0 44. Zhang, Fangmei, et al. "Enzymatic determination of uric acid using water-soluble CuInS/ZnS quantum dots as a fluorescent probe." Microchimica Acta 185.11 (2018): 1-8.https://doi.org/10.1007/s00604-018-3030-0 45. Longbin Xu, Xu He, Pinyi Ma, Xin Liu, Fangmei Zhang, Ying Sun, Daqian Song, Xinghua Wang,A water-soluble fluorescent probe for the sensitive detection of endogenous alkaline phosphatase in living cells,Dyes and Pigments,Volume 159,2018,Pages 584-589, 46. Hou, Xiaorong, et al. "Development of an immobilized liposome chromatography method for screening and characterizing α-glucosidase-binding compounds." Journal of Chromatography B 1148 (2020): 122097.https://doi.org/10.1016/j.jchromb.2020.122097 47. Xiaokui Huo, Xiangge Tian, Yannan Li, Lei Feng, Yonglei Cui, Chao Wang, Jingnan Cui, Chengpeng Sun, Kexin Liu, Xiaochi Ma, A highly selective ratiometric fluorescent probe for real-time imaging of β-glucuronidase in living cells and zebrafish, Sensors and 48. [IF=10.257] Xue–Lian Hu et al."Switchable fluorescence of gold nanoclusters for probing the activity of alkaline phosphatase and its application in immunoassay."Biosens Bioelectron. 2016 Mar;77:666 49. [IF=7.46] Xiaokui Huo et al."A highly selective ratiometric fluorescent probe for real-time imaging of β-glucuronidase in living cells and zebrafish."Sensor Actuat B-Chem. 2018 Jun;262:508 50. [IF=7.46] Lihua Chen et al."A novel label-free electrochemical immunosensor modified by glutathione and hyaluronic acid for the ultrasensitive and ultraselective detection of brucellosis in dilute serum."Sensor Actuat B-Chem. 2019 May;287:510 51. [IF=7.1] Xin Fang et al."Tuning surface states to achieve the modulated fluorescence of carbon dots for probing the activity of alkaline phosphatase and immunoassay of α-fetoprotein."Sensor Actuat B-Chem. 2018 Mar;257:620 52. [IF=6.331] Yingchun Xia et al."Polycarbonate-based core-crosslinked redox-responsive nanoparticles for targeted delivery of anticancer drug."J Mater Chem B. 2018 May;6(20):3348-3357 53. [IF=6.331] Wei Zhao et al."Transferrin-decorated, MoS2-capped hollow mesoporous silica nanospheres as a self-guided chemo–photothermal nanoplatform for controlled drug release and thermotherapy."J Mater Chem B. 2017 Sep;5(35):7403-7414 54. [IF=5.833] Zhang Fangmei et al."Enzymatic determination of uric acid using water-soluble CuInS/ZnS quantum dots as a fluorescent probe."Microchim Acta. 2018 Nov;185(11):1-8 55. [IF=5.833] Wu Tiaodi et al."An ultrasensitive electrochemical sensor based on cotton carbon fiber composites for the determination of superoxide anion release from cells."Microchim Acta. 2019 Mar;186(3):1-9 56. [IF=5.582] Dongling Cao et al."Polymeric prodrugs conjugated with reduction-sensitive dextran–camptothecin and pH-responsive dextran–doxorubicin: an effective combinatorial drug delivery platform for cancer therapy."Polym Chem-Uk. 2016 Jun;7(25):4198-4212 57. [IF=5.339] Fangmei Zhang et al."Rapid aqueous synthesis of CuInS/ZnS quantum dots as sensor probe for alkaline phosphatase detection and targeted imaging in cancer cells."Talanta. 2018 Nov;189:411 58. [IF=5.268] Wenhai Lin et al."Reduction-sensitive amphiphilic copolymers made via multi-component Passerini reaction for drug delivery."Colloid Surface B. 2015 Feb;126:217 59. [IF=4.952] Meng Niu et al."Inhibitory effects of ultrasound combined with ascorbic acid or glutathione on enzymatic darkening of whole-wheat raw noodles."Lwt Food Sci Technol. 2014 Dec;59:901 60. [IF=4.749] Guoqing Ma et al."Dual-Responsive Polyphosphoester-Doxorubicin Prodrug Containing a Diselenide Bond: Synthesis, Characterization, and Drug Delivery."Acs Biomater Sci Eng. 2018;4(7):2443–2452 61. [IF=4.613] Longbin Xu et al."A water-soluble fluorescent probe for the sensitive detection of endogenous alkaline phosphatase in living cells."Dyes Pigments. 2018 Dec;159:584 62. [IF=11.413] Zhenhao Tian et al."A NIR fluorescent probe for Vanin-1 and its applications in imaging, kidney injury diagnosis, and the development of inhibitor."Acta Pharm Sin B. 2021 Jun;: 63. [IF=8.183] Zhicheng Zhang et al."Versatile iron-vitamin K 3 derivative-based nanoscale coordination polymer augments tumor ferroptotic therapy."Nano Res. 2021 Jul;14(7):2398-2409 64. [IF=6.986] Xiangge Tian et al."Visual High-Throughput Screening for Developing a Fatty Acid Amide Hydrolase Natural Inhibitor Based on an Enzyme-Activated Fluorescent Probe."Anal Chem. 2020;92(14):9493–9500 65. [IF=6.785] Xiangge Tian et al."Endoplasmic Reticulum Targeting Ratiometric Fluorescent Probe for Carboxylesterase 2 Detection in Drug-Induced Acute Liver Injury."Anal Chem. 2019;91(24):15840–15845 66. [IF=6.707] Pengyuan Shan et al."Effects of silver nanoclusters on the spectral properties for fluorescein isothiocyanate with restrained photobleaching."Appl Surf Sci. 2021 May;548:149287 67. [IF=6.419] Lili Ren et al."RGD-targeted redox responsive nano micelle: co-loading docetaxel and indocyanine green to treat the tumor."Drug Deliv. 2021;28(1):2024-2032 68. [IF=6.306] Fei Chen et al."Visual determination of azodicarbonamide in flour by label-free silver nanoparticle colorimetry."Food Chem. 2021 Feb;337:127990 69. [IF=6.023] Ying Liu et al."Mechanistic study of bergamottin-induced inactivation of CYP2C9."Food Chem Toxicol. 2021 Jul;153:112278 70. [IF=5.582] Lei Xu et al."Facile construction of noncovalent graft copolymers with triple stimuli-responsiveness for triggered drug delivery."Polym Chem-Uk. 2021 Apr;12(14):2152-2164 71. [IF=5.279] Yujiao Cheng et al."Methanethiol, an Off-Flavor Produced from the Thermal Treatment of Mandarin Juices: A Study of Citrus Sulfur Volatiles."J Agr Food Chem. 2020;68(4):1030–1037 72. [IF=5.076] Lulu Liu et al."Functionalized MoS2 Nanoflowers with Excellent Near-Infrared Photothermal Activities for Scavenging of Antibiotic Resistant Bacteria."Nanomaterials-Basel. 2021 Nov;11(11):2829 73. [IF=4.35] Jiangxiong Zhu et al."Valorization of Polysaccharides Obtained from Dark Tea: Preparation, Physicochemical, Antioxidant, and Hypoglycemic Properties."Foods. 2021 Oct;10(10):2276 74. [IF=4.204] Zhu Mingyue et al."A highly selective fluorescent probe for real-time imaging of UDP-glucuronosyltransferase 1A8 in living cells and tissues."Frontiers of Chemical Science and Engineering. 2021 Jun 29 75. [IF=4.142] Li Dan et al."Sensitive ratiometric fluorescence assay for detecting xanthine in serum based on the inner filter effect of enzyme-catalyzed oxidation products to silicon nanoparticles."Anal Bioanal Chem. 2021 Feb;413(5):1405-1415 76. [IF=4.076] Ahui Sun et al."A Zinc Coordination Polymer Sensor for Selective and Sensitive Detection of Doxycycline Based on Fluorescence Enhancement."Cryst Growth Des. 2021;21(9):4971–4978 77. [IF=4.015] Hao Yu et al."Effects of low-molecular-weight organic acids/thiols on hydroxyl radical production from natural siderite oxidation."Chem Geol. 2021 Dec;584:120537 78. [IF=3.591] Dongdong Huang et al."Preparation of metal–organic frameworks with bimetallic linkers and corresponding properties."New J Chem. 2019 May;43(19):7243-7250 79. [IF=3.205] Xiaorong Hou et al."Development of an immobilized liposome chromatography method for screening and characterizing α-glucosidase-binding compounds."J Chromatogr B. 2020 Jul;1148:122097 80. [IF=3.167] Fuli Sun et al."Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment."J Food Sci. 2019 Dec;84(12):3584-3593 81. [IF=1.965] Jiang Tingting et al."Bergaptol, a mechanism-based inactivator of CYP2C9."Med Chem Res. 2020 Jul;29(7):1230-1237 82. [IF=3.935] Huan Wu et al."Use of cellular metabolomics and lipidomics to decipher the mechanism of Huachansu injection-based intervention against human hepatocellular carcinoma cells."J Pharmaceut Biomed. 2022 Apr;212:114654 83. [IF=6.165] Shan Lu et al."Colorimetric and fluorescent dual-channel sensor array based on Eriochrome Black T/Eu3+ complex for sensing of multiple tetracyclines."J Mol Liq. 2022 Apr;351:118371 84. [IF=3.361] Bingchen Han et al."The fluorescence mechanism of carbon dots based on the separation and identification of small molecular fluorophores."RSC Advances. 2022 Apr;12(19):11640-11648 85. [IF=6.475] Zhen Xia et al."Purification, identification, and antioxidative mechanism of three novel selenium-enriched oyster antioxidant peptides."FOOD RESEARCH INTERNATIONAL. 2022 Jul;157:111359 86. [IF=4.105] Cong Wang et al."Heteronuclear MOF-based fluorescent sensor for the detection of tetracycline antibiotics."APPLIED ORGANOMETALLIC CHEMISTRY |
微信搜索化工百科或扫描下方二维码,添加化工百科小程序,随时随地查信息!