6902-77-8
京尼平((+)-Genipin)
CAS: 6902-77-8
化学式: C11H14O5
| 中文名 | 京尼平 |
| 英文名 | (+)-Genipin |
| 别名 | 京尼平 栀子苷元 格尼泊素 京尼平(栀子苷元 GENIPIN 京尼平 格尼泊素,GENIPIN 京尼平(栀子苷元,格尼泊素) (1S,2R,6S)-2-羟基-9-(羟甲基)-3-氧代二环丙[4.3.0]壬-4,8-二烯-5-甲酸甲酯 |
| 英文别名 | enipin Genipin GENIPIN (+)-Genipin cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate 1,4A,5,7A-Tetrahydro-1-Hydroxy-7-(Hydroxymethyl)-Cyclopenta(C)Pyran-4-Carboxylic Acid Methyl Ester 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (1R)-1,4aα,5,7aα-Tetrahydro-1-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester (1R)-1,4aα,5,7aα-Tetrahydro-1α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester |
| CAS | 6902-77-8 |
| EINECS | 636-196-5 |
| 化学式 | C11H14O5 |
| 分子量 | 226.23 |
| InChI | InChI=1/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1 |
| InChIKey | AZKVWQKMDGGDSV-BCMRRPTOSA-N |
| 密度 | 1.1230 (rough estimate) |
| 熔点 | 118.0 to 123.0 °C |
| 沸点 | 287.83°C (rough estimate) |
| 比旋光度 | (MeOH)+135 |
| 闪点 | 164.9°C |
| 蒸汽压 | 1.17E-08mmHg at 25°C |
| 溶解度 | DMSO: ≥ 25 mg/mL |
| 折射率 | 1.4720 (estimate) |
| 酸度系数 | 12.06±0.60(Predicted) |
| 存储条件 | Inert atmosphere,Room Temperature |
| 敏感性 | Easily absorbing moisture |
| 外观 | 粉末 |
| 颜色 | White to Almost white |
| 最大波长(λmax) | ['240nm(MeOH)(lit.)'] |
| 物化性质 | 白色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于栀子果实。 |
| MDL号 | MFCD00888600 |
| 体外研究 | Genipin increases mitochondrial membrane potential, increased ATP levels, closed KATP channels, and stimulated insulin secretion in pancreatic islet cells. Genipin causes suppression of insulin signal transduction through hyperactivation of c-Jun N-terminal kinase (JNK) and subsequent serine phosphorylation of insulin receptor substrate-1 (IRS-1), thus impairing insulin-stimulated glucose uptake in 3T3-L1 adipocytes. Genipin activates IRS-1, PI3-K, and downstream signaling pathway and increases concentrations of calcium, resulting in glucose transporter 4 (GLUT4) translocation and glucose uptake increase in C2C12 myotubes. Cytochrome c content increases significantly in the cytosol of Genipin-treated FaO cells. Activation of caspase-3 and caspase-7 is ultimately responsible for Genipin-induced apoptotic process in hepatoma cells. ROS level notably increases in Hep3B cells treated with 200 μM Genipin. |
| 危险品标志 | Xn - 有害物品 |
| 风险术语 | 22 - 吞食有害。 |
| 安全术语 | S3/14 - S36/37/39 - 穿戴适当的防护服、手套和护目镜或面具。 |
| 危险品运输编号 | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | GY5828000 |
| 海关编号 | 29329990 |
| Hazard Class | 6.1 |
| Packing Group | III |
| 参考资料 展开查看 | 1. 刘涵 尹子楚 蔡玉荣 等. 丝素蛋白/多巴胺医用粘合剂的制备及其性能[J]. 浙江理工大学学报 2020 043(003):308-314. 2. 陈星光, 邹承达, 宿广昊,等. 负载富血小板纤维蛋白的新型水凝胶对BMSCs体外成软骨分化的影响[J]. 江苏大学学报(医学版), 2018, v.28；No.142(04):20-25. 3. 冯家懿, 张圳, 果卉,等. 药学本科药物分析的课外科研实践探索[J]. 广州化工, 2018, 046(002):128-130. 4. 刘蔚 常杰 武毅君 等. 健骨痛消丸中活性成分的检测及其抗凝血作用的研究[J]. 河南大学学报（医学版） 2020年39卷2期 80-84页 2020. 5. 刘锟,王健英,魏莉,潘颖宜,袁颖.HPLC法测定杜仲皮、叶、雄花中8种成分[J].中成药,2021,43(03):686-691. 6. Wang, Wei, Dan-Dan Tian, and Zhang-Jin Zhang. "In Vitro Effects of Concomitant Use of Herbal Preparations on Cytochrome P450s Involved in Clozapine Metabolism." Molecules 21.5 (2016): 597.https://doi.org/10.3390/molecules21050597 7. Zhang, Shan, et al. "Mass-production of fluorescent chitosan/graphene oxide hybrid microspheres for in vitro 3D expansion of human umbilical cord mesenchymal stem cells." Chemical Engineering Journal 331 (2018): 675-684.https://doi.org/10.1016/j.cej.2017.0 8. Jiao, Yanting, et al. "Genipin, a natural AKT inhibitor, targets the PH domain to affect downstream signaling and alleviates inflammation." Biochemical pharmacology 170 (2019): 113660.https://doi.org/10.1016/j.bcp.2019.113660 9. Lu, Zhi Hua, Chun Guang Yin, and Dong Mei Zhao. "Biomimetic scaffolds containing chitosan and hydroxyapatite for bone tissue engineering." Advanced Materials Research. Vol. 971. Trans Tech Publications Ltd, 2014.https://doi.org/10.4028/www.scientific.net/A 10. Wang, Ruihua et al. “A Mechanism for the Temporal Potentiation of Genipin to the Cytotoxicity of Cisplatin in Colon Cancer Cells.” International journal of medical sciences vol. 13,7 507-16. 29 Jun. 2016, doi:10.7150/ijms.15449 11. Wang, Ruihua et al. “A Mechanism for the Temporal Potentiation of Genipin to the Cytotoxicity of Cisplatin in Colon Cancer Cells.” International journal of medical sciences vol. 13,7 507-16. 29 Jun. 2016, doi:10.7150/ijms.15449 12. [IF=10.652] Shan Zhang et al."Mass-production of fluorescent chitosan/graphene oxide hybrid microspheres for in vitro 3D expansion of human umbilical cord mesenchymal stem cells."Chem Eng J. 2018 Jan;331:675 13. [IF=4.759] Lu Wang et al."A strategy for identification and structural characterization of compounds from Gardenia jasminoides by integrating macroporous resin column chromatography and liquid chromatography-tandem mass spectrometry combined with ion-mobility spectr 14. [IF=4.759] Wenhua Ji et al."Water-compatible micron-sized monodisperse molecularly imprinted beads for selective extraction of five iridoid glycosides from Cornus officinalis fructus."J Chromatogr A. 2017 Jun;1504:1 15. [IF=4.223] Wang Ruihua et al."UCP2- and non-UCP2-mediated electric current in eukaryotic cells exhibits different properties."Environ Sci Pollut R. 2015 Dec;22(24):19618-19631 16. [IF=4.142] Ji Wenhua et al."Superhydrophilic molecularly imprinted polymers based on a single cross-linking monomer for the recognition of iridoid glycosides in Di-huang pills."Anal Bioanal Chem. 2018 Oct;410(25):6539-6548 17. [IF=3.267] Yu Qian et al."Lactobacillus casei Strain Shirota Enhances the In Vitro Antiproliferative Effect of Geniposide in Human Oral Squamous Carcinoma HSC-3 Cells."Molecules. 2018 May;23(5):1069 18. [IF=3.119] Yingcong He et al."Modifying collagen with alendronate sodium for bone regeneration applications."Rsc Adv. 2018 May;8(30):16762-16772 19. [IF=1.367] Yong Hu et al."Study on the preparation and drug release property of soybean selenoprotein/carboxymethyl chitosan composite hydrogel."J Polym Eng. 2018 Nov;38(10):963-970 20. [IF=6.953] Xin Meng et al."Chitosan/alginate/hyaluronic acid polyelectrolyte composite sponges crosslinked with genipin for wound dressing application."Int J Biol Macromol. 2021 Jul;182:512 21. [IF=4.411] Chunnan Li et al."Screening of the Hepatotoxic Components in Fructus Gardeniae and Their Effects on Rat Liver BRL-3A Cells."Molecules. 2019 Jan;24(21):3920 22. [IF=3.263] Tianyi Zhao et al."Protective effects of genipin on ethanol-induced acute gastric injury in mice by inhibiting NLRP3 inflammasome activation."Eur J Pharmacol. 2020 Jan;867:172800 23. [IF=6.321] Yujie Zheng et al."Microemulsion Delivery System Improves Cellular Uptake of Genipin and Its Protective Effect against Aβ1-42-Induced PC12 Cell Cytotoxicity."Pharmaceutics. 2022 Mar;14(3):617 24. [IF=5.717] Man Zhang et al."Dietary Flavone Baicalein Combinate with Genipin Attenuates Inflammation Stimulated by Lipopolysaccharide in RAW264.7 Cells or Pseudomonas aeruginosa in Mice via Regulating the Expression and Phosphorylation of AKT."Nutrients. 2021 Dec;13 |
6902-77-8 - 简介
京尼平是一种有机化合物，化学名为2-(2'-氨基-5'-氯苯基)丙酸。以下是关于京尼平的性质、用途、制法和安全信息的介绍：
性质：
京尼平是一种白色结晶固体，具有特殊的苯氧基胺气味。它几乎不溶于水，能溶于醇和氯代烃。
用途：
京尼平主要用作害虫和杂草的除草剂。它可以有效控制许多常见的草本杂草、藤本植物和一些谷物的杂草。
制法：
京尼平的制法通常是通过对2-氨基苯甲酸与氯乙酸的缩合反应制得。具体步骤包括将2-氨基苯甲酸和氯乙酸反应，在适当的条件下进行加热和反应碱性条件下酯化，得到最后的产品京尼平。
安全信息：
京尼平是一种有毒的化合物，对皮肤、眼睛和呼吸道有刺激性。在使用或接触京尼平时，应戴好防护手套、护目镜和口罩。在处理京尼平后，应彻底清洗受到影响的皮肤，并注意避免吞咽或吸入。
性质：
京尼平是一种白色结晶固体，具有特殊的苯氧基胺气味。它几乎不溶于水，能溶于醇和氯代烃。
用途：
京尼平主要用作害虫和杂草的除草剂。它可以有效控制许多常见的草本杂草、藤本植物和一些谷物的杂草。
制法：
京尼平的制法通常是通过对2-氨基苯甲酸与氯乙酸的缩合反应制得。具体步骤包括将2-氨基苯甲酸和氯乙酸反应，在适当的条件下进行加热和反应碱性条件下酯化，得到最后的产品京尼平。
安全信息：
京尼平是一种有毒的化合物，对皮肤、眼睛和呼吸道有刺激性。在使用或接触京尼平时，应戴好防护手套、护目镜和口罩。在处理京尼平后，应彻底清洗受到影响的皮肤，并注意避免吞咽或吸入。
最后更新：2024-04-09 02:00:10
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产品名: 京尼平(10mM in DMSO,无菌) 去供应商网站查看 询盘CAS: IG00801
产地: 北京
包装: 1ml/瓶
规格: IG00801-1ml
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库存: 现询
电话: 010-50973130
手机: 17801761073(微信同号)
电子邮件: 3193328036@qq.com
QQ: 3193328036
微信: 17801761073
产品描述: 索莱宝直销,欢迎来询
提供多种规格现货供应
产品名: 京尼平(10mM in DMSO,无菌) 去供应商网站查看 询盘CAS: IG00801
产地: 北京
包装: 1ml/瓶
规格: IG00801-1ml
价格: 电话、微信、QQ、邮件
库存: 现询
电话: 010-50973130
手机: 17801761073(微信同号)
电子邮件: 3193328036@qq.com
QQ: 3193328036
微信: 17801761073
产品描述: 索莱宝直销,欢迎来询
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