S-烯丙基-L-半胱氨酸
S-烯丙基-L-半胱氨酸 性质
| 熔点 | 235-236℃ |
|---|---|
| 沸点 | 300℃ |
| 密度 | 1.191 |
| FEMA | 4322 | S-ALLYL-L-CYSTEINE |
| 闪点 | 135℃ |
| 储存条件 | -20°C |
| 溶解度 | H2O:>10mg/mL |
| 形态 | 粉末 |
| 酸度系数(pKa) | 2.07±0.10(Predicted) |
| 颜色 | 白色至米色 |
| 气味 (Odor) | 0.10% 的丙二醇溶液。烤熟的气味 |
| 香型 | roasted |
| 旋光度 (Optical Rotation) | [α]/D -8 to -15°, c = 1 in H2O |
| 水溶解性 | H2O: >10mg/mL |
| JECFA Number | 1710 |
| 稳定性 | 感光 |
| 化妆品成分功效 | BLEACHING |
| InChI | 1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1 |
| InChIKey | ZFAHNWWNDFHPOH-YFKPBYRVSA-N |
| SMILES | N[C@@H](CSCC=C)C(O)=O |
| LogP | 1.31 |
| CAS 数据库 | 21593-77-1(CAS DataBase Reference) |
S-烯丙基-L-半胱氨酸 用途与合成方法
It is found that S-Allyl-L-cysteine could protect against amyloid-protein (A)-and tunicamycin-induced cell death in differentiated PC12 cells. Simultaneously applied S-Allyl-L-cysteine (1 μM) suppresses the cell death induced by Aβ 25-35 and Aβ 1-40 in a concentration-dependent manner, and neuronal integrity is almost completely retained. Simultaneously applied S-Allyl-L-cysteine significantly decreases the Aβ-induced level of ROS. The TEAC value of S-Allyl-L-cysteine is lower than that of oxidized GSH, and no antioxidant activity is observed. Intracellular GSH levels remains unaffected by treatment of neurons with S-Allyl-L-cysteine for 24 h. Furthermore, the increase in caspase-12 protein expression is suppressed by simultaneously adding 1 μM S-Allyl-L-cysteine . S-Allyl-L-cysteine up to a concentration 1.0 mM does not exhibit any cytotoxic impact on morphology of myoblast and myotubes in culture observed under bright field microscope. TNF treatment leads to a significant decrease in the intracellular CK activity while S-Allyl-L-cysteine pre-treatment to TNF treated myotubes decreases the release of CK in media. S-Allyl-L-cysteine pre-treatment decreases the level of active form of this enzyme in S-Allyl-L-cysteine+TNF group. Similar observations are recorded at mRNA level for caspase-3. These results illustrate that S-Allyl-L-cysteine regulates apoptotic signals via suppressing the transcription and thus protein expression of caspase-3.
232953-12-7
21593-77-1
以BocSacOMe(9.92 g,36.02 mmol)为原料,在250 mL圆底烧瓶中溶解于CH2Cl2(100 mL)。在氩气保护下,向溶液中加入TFA(10 mL),室温搅拌反应混合物3小时。通过TLC(展开剂:150% EtOAc的石油醚溶液)监测反应进度,确认原料完全消耗(Rf = 0.4)。随后,通过旋转蒸发去除溶剂,得到的黄色残余物在真空下短暂干燥。将粘性残余物溶解于THF(30 mL)中,冷却至0℃。向搅拌的溶液中加入LiOH(72 mL,5M水溶液)。移除冰浴,反应混合物在室温下继续搅拌1小时。反应完成后,用100 mL H2O稀释,使用DOWEX(R)树脂中和至pH <7(通过pH试纸检测)。将所有树脂转移至空柱中,用500 mL H2O(重力流)洗涤,弃去流出液。产物用5% NH4OH水溶液洗脱,并用50% H2O(洗脱液)洗涤。收集含有(R)-3-(烯丙基硫基)-2-氨基丙酸的级分(Rf = 0.6),通过旋转蒸发浓缩,得到黄色固体。进一步通过柱色谱纯化[洗脱剂比例:7:2:1 iPrOH:MeOH:NH4OH(25% 水溶液)],得到白色晶体Sac(3.29 g,57%)。熔点:212-213℃。1H NMR(400 MHz,D2O):δH = 2.5-2.70(2H,ABX系统,J = 13.3, 5.3, 6.7 Hz,CH2SAllyl),3.06(2H,d,J = 7.2 Hz,CH2CH=CH2),3.28(1H,dd,J = 6.7, 5.3 Hz,Hα),5.02-5.09(2H,m,HC=CH2),5.71(1H,m,HC=CH2)。
参考文献:
[1] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9642 - 9643
[2] Patent: US2012/178913, 2012, A1. Location in patent: Page/Page column 10-11
S-烯丙基-L-半胱氨酸 价格(试剂级)
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026-03-03 | S4791 | S- 烯丙基别半胱氨酸,蒜氨酸 | 21593-77-1 | 25mg | 795.41 |
| 2025-12-22 | HY-W013573 | S-烯丙基-L-半胱氨酸 | 21593-77-1 | 1 mg | 100 |