四氢姜黄素
| 中文名称 | 四氢姜黄素 |
|---|---|
| 中文同义词 | TETRAHYDROCUCUMIN 四氢姜黄素;纳米包裹辅酶四氢姜黄素;生物活性四氢姜黄素;水溶性四氢姜黄素;7-双(4-羟基-3-甲氧基苯基)庚烷-3;四氢姜黄素(标准品);1,7-二(3-甲氧基-4-羟基苯基)庚烷-3,5-二酮;四氢姜黄素, 来源于姜黄 |
| 英文名称 | Tetrahydrocurcumin |
| 英文同义词 | SabiWhite-;3,5-Heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-;1,7-bis(4-hydroxy-3-methoxy-phenyl)heptane-3,5-dione;Tetrahydrocurcumin;TETRAHYDROCURCUMINOID;Aids110028;Aids-110028;Nsc687845 |
| CAS号 | 36062-04-1 |
| 分子式 | C21H24O6 |
| 分子量 | 372.41 |
| EINECS号 | 609-201-3 |
| 植物来源 | 姜黄 |
| 相关类别 | 四氢姜黄素;原料药API;其他原料;标准品-对照品;中药对照品;对照品;标准品;植物提取物;香精香料;日化美白原料;中间体;原料;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;化妆品原料;对照品-中药对照品;其它酚类;标准品 -中药标准品;标准品,对照品;化工原料;合成材料中间体;医药、农药及染料中间体;色素;标准提取物;化学试剂 |
| Mol文件 | 36062-04-1.mol |
| 结构式 | ![]() |
四氢姜黄素 性质
| 熔点 | 95-97 ºC |
|---|---|
| 沸点 | 564.1±45.0 °C(Predicted) |
| 密度 | 1.222 |
| 闪点 | 196℃ |
| 储存条件 | Inert atmosphere,Room Temperature |
| 溶解度 | 可溶于DMSO(轻微)、甲醇(轻微、加热) |
| 酸度系数(pKa) | 9.12±0.10(Predicted) |
| 形态 | 粉末 |
| 颜色 | 浅黄色至厚黄色 |
| BRN | 3485469 |
| 稳定性 | 感光 |
| 主要应用 | 食品和饮料 |
| 化妆品成分功效 | 抗氧化剂 |
| InChI | InChI=1S/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3 |
| InChIKey | LBTVHXHERHESKG-UHFFFAOYSA-N |
| SMILES | C(C1=CC=C(O)C(OC)=C1)CC(=O)CC(=O)CCC1=CC=C(O)C(OC)=C1 |
| LogP | 2.728 (est) |
四氢姜黄素为天然的姜黄根提取物中主要的美白活性成分,不仅具有最强的酪氨酸酶抑制活性,还具有极好的化学稳定性,而且外观为无味的白色粉末,从而克服了普通姜黄提取物化学不稳定易使皮肤染色的缺陷。普通的姜黄提取物为黄色,化学稳定性差,具有光敏性,在光照下,容易和皮肤发生化学反应而使皮肤染色。四氢姜黄素为天然功能性美白原料,具有抑制酪氨酸酶的强效活性,美白效果优于我们熟知的熊果苷,能有效抑制氧自由基(oxygen free radicals)的生成并能清除已经形成的自由基,具有明显的抗氧化、抑制黑色素、修复祛斑、抗炎活性、阻断炎症过程等。此外,对自由基的抑制、对各种炎因子脂氧和酶、胶原蛋白酶、透明质酸酶的抑制,体现了四氢姜黄素潜在的抗衰老功效。四氢姜黄素添加到化妆品中对人体肌肤无刺激或致敏的副作用,且能安全有效地发挥其作用。Tetrahydrocurcumin 在姜黄 (Curcuma longa) 中发现的一种姜黄素,是由 Curcumin 还原产生的。Tetrahydrocurcumin 抑制 CYP2C9 和 CYP3A4。
|
CYP2C9
|
CYP3A4
|
Human Endogenous Metabolite
|
Autophagy
|
Tetrahydrocurcumin (THC) has a number of attractive properties not shared with Curcumin that may make it superior. Tetrahydrocurcumin inhibited lipoxygenase as low as 1 μM. Tetrahydrocurcumin is tested for its ability to inhibit CYP2C9, CYP3A4, CYP1A2 and CYP2D6. Tetrahydrocurcumin yields dose-dependent inhibition of CYP2C9, and to a lesser extent, CYP3A4. Tetrahydrocurcumin exhibits maximum inhibition of CYP2C9 and CYP3A4 at 50 to 100 μM. Tetrahydrocurcumin does not show a consistent dose-response inhibition of CYP1A2 or CYP2D6 over the range of concentrations tested. In some cases, the percent inhibition exceeds 100%. The effect of Tetrahydrocurcumin on cancer cell viability is measured. Sup-T1 cells, T-cell lymphoblastic lymphoma cells, are treated with Tetrahydrocurcumin to determine its ability to induce growth inhibition using an MTS assay, and the corresponding IC50 values are in the mid-to-high micromolar range.
The serum Tetrahydrocurcumin (THC) concentration versus time curve shows that more than one absorption and distribution phase is present. Initially, a rapid absorption phase with an average Tmax of 6.8 μg/mL at 1 h is observed, followed by a short elimination phase. This is followed by two redistributions with two smaller Tetrahydrocurcumin maxima at 6 and 24 h. Both redistribution phases has similar maxima of about 1 μg/mL. The total amount of Tetrahydrocurcumin excrets unchanged in urine was up to 8 μg at 24 h.
458-37-7
36062-04-1
以(1E,6E)-1,7-双(4-羟基-3-甲氧基苯基)庚-1,6-二烯-3,5-二酮为起始原料合成四氢姜黄素的一般步骤:将1g铂-铁-镍氢氧化物复合纳米粒子催化剂与100g姜黄素加入装有300ml乙醇的反应烧瓶中,于24℃室温条件下搅拌反应1小时。反应完成后,通过减压蒸馏除去溶剂,得到98g淡黄色粘性物质。将该物质溶解于400ml乙醇中,随后浓缩至150ml。将浓缩液置于冰箱中静置结晶,最终获得92.9g淡黄色固体产物,收率为92.9%。
参考文献:
[1] Patent: CN104496779, 2017, B. Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018-0023
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 6, p. 495 - 497
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 22, p. 6175 - 6181
[4] Bioscience, biotechnology, and biochemistry, 1995, vol. 59, # 9, p. 1609 - 1612
[5] Biochemical Pharmacology, 1996, vol. 52, # 4, p. 519 - 525
安全信息
| WGK Germany | 3 |
|---|---|
| 存储类别 | 11 - 可燃固体 |
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026/06/05 | HY-N0893R | 四氢姜黄素 Tetrahydrocurcumin (Standard) | 36062-04-1 | 5 mg | 1250元 |
| 2026/06/05 | HY-N0893R | 四氢姜黄素 Tetrahydrocurcumin (Standard) | 36062-04-1 | 10 mg | 2000元 |
