21593-77-1
基本信息
S- 烯丙基-L-半胱氨酸
烯丙基-L-半胱氨酸
DEOXYALLIIN
(L)-3-(ALLYLSULFENYL)-ALANINE
L-DEOXYALLIIN
(R)-ALLYLTHIO-2-AMINOPROPIONIC ACID
S-ALLYL-L-CYSTEINE
s-allylcysteine
Allylcysteine
物理化学性质
| 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 |
| 酸度系数(pKa) | 2.07±0.10(Predicted) |
| 形态 | 粉末 |
| 颜色 | 白色至米色 |
| 气味 (Odor) | at 0.10 % in propylene glycol. cooked roasted |
| 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 |
| LogP | 1.31 |
| CAS 数据库 | 21593-77-1(CAS DataBase Reference) |
安全数据
| 危险性符号(GHS) |  GHS07 |
| 警示词 | 警告 |
| 危险性描述 | H317 |
| 防范说明 | P280 |
| 危险品标志 | Xi |
| 危险类别码 | 43 |
| 安全说明 | 36/37 |
| WGK Germany | 3 |
| RTECS号 | HA2466200 |
| 海关编码 | 2930.90.9250 |
制备方法
![L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-S-2-propen-1-yl-, methyl ester](/CAS/20210305/GIF/232953-12-7.gif)
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
图谱信息
S-烯丙基-L-半胱氨酸(21593-77-1)质谱(MS)S-烯丙基-L-半胱氨酸(21593-77-1)核磁图(1HNMR)S-烯丙基-L-半胱氨酸(21593-77-1)红外图谱(IR1)S-烯丙基-L-半胱氨酸(21593-77-1)红外图谱(IR2)S-烯丙基-L-半胱氨酸价格(试剂级)
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2025/12/22 | HY-W013573 | S-烯丙基-L-半胱氨酸 S-Allyl-L-cysteine | 21593-77-1 | 1 mg | 100元 |
| 2025/12/22 | HY-W013573 | S- 烯丙基别半胱氨酸,蒜氨酸 S-Allyl-L-cysteine | 21593-77-1 | 10mM * 1mLin Water | 177元 |
| 2025/12/22 | HY-W013573 | S-烯丙基-L-半胱氨酸 S-Allyl-L-cysteine | 21593-77-1 | 5 mg | 190元 |
常见问题列表
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.