六氢姜黄素
| 中文名称 | 六氢姜黄素 |
|---|---|
| 中文同义词 | 六氢姜黄素;六氢姜黄素?, BR;COX-2抑制剂(HEXAHYDROCURCUMIN);六氢姜黄素 标准品;5-羟基-1,7-双(4-羟基-3-甲氧基苯基)庚烷-3-酮;六氢姜黄素,10 MM DMSO 溶液;Hexahydrocurcumin (Synonyms: 六氢姜黄素);Hexahydrocurcumin (Synonyms: 六氢姜黄素) |
| 英文名称 | HEXAHYDROCURCUMIN |
| 英文同义词 | HEXAHYDROCURCUMIN;5-Hydroxy-1-(4-hydroxy-3-Methoxycyclohexyl)-7-(4-hydroxy-3-Methoxyphenyl)heptan-3-one;(RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone;1,7-Bis(3-methoxy-4-hydroxyphenyl)-5-hydroxy-3-heptanone;1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-hydroxyheptan-3-one;5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone;Hexahydrocurcumin, BR;3-Heptanone, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)- |
| CAS号 | 36062-05-2 |
| 分子式 | C21H26O6 |
| 分子量 | 374.43 |
| EINECS号 | |
| 相关类别 | 细胞生物学试剂;对照品;中药对照品;标准品;植物提取物;标准品 -对照药材;其它酚类;标准品-对照品;标准品，对照品;对照品 |
| Mol文件 | 36062-05-2.mol |
| 结构式 |  |
六氢姜黄素 性质
| 熔点 | 80-82℃ |
|---|---|
| 沸点 | 622.6±55.0 °C(Predicted) |
| 密度 | 1.226 |
| 闪点 | 218℃ |
| 储存条件 | 2-8°C |
| 溶解度 | 可溶于氯仿（少量）、乙酸乙酯（少量）、DCM、DMSO |
| 酸度系数(pKa) | 10.02±0.20(Predicted) |
| 形态 | 固体 |
| 颜色 | 淡黄色低 |
| BRN | 2486876 |
| 主要应用 | food and beverages |
| InChI | 1S/C21H26O6/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/h5-6,9-12,16,22,24-25H,3-4,7-8,13H2,1-2H3 |
| InChIKey | RSAHICAPUYTWHW-UHFFFAOYSA-N |
| SMILES | O=C(CC(O)CCC1=CC(OC)=C(O)C=C1)CCC2=CC(OC)=C(O)C=C2 |
姜黄素及其还原产物可在UDP葡糖醛酸转移酶的作用下，形成姜黄素葡糖醛酸结合物。部分姜黄素在人苯酚磺基转移酶同工酶(SULF1A1和SULF1A3)的催化下，形成姜黄素的磺酸盐，即磺酸姜黄素，其与姜黄素相比生物活性较低。Holder等人报道，在大鼠体内姜黄素的主要代谢产物是四氢、六氢姜黄素的葡糖醛酸结合物，胆汁代谢物是少量的二氢阿魏酸和微量的阿魏酸。
健康受试者单次口服10g或12g姜黄素的药代动力学研究发现，约4h后血浆中检测到姜黄素葡糖醛酸和磺酸结合物。通常口服给药后，在1至2小时内观察到姜黄素峰值血液浓度，并在大约12小时后变得检测不到。Hexahydrocurcumin 是姜黄素的主要代谢产物之一，是一种选择性的口服活性 COX-2 抑制剂，对 COX-1 无活性。Hexahydrocurcumin 具有抗氧化，抗癌和抗炎的作用。
|
COX-2
|
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) treatment significantly decreased the viability of HT-29 colon cancer cells in a time- and concentration-dependent. The respective IC
50
values for 24 and 48 h of Hexahydrocurcumin exposureare 77.05 and 56.95, respectively.
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) combined with 5-fluorouracil (5-FU; 5 µM) markedly reduces the COX-2 expression. The level of COX-1 is not altered.
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) combined with 5-fluorouracil (5-FU; 5 µM) markedly reduces the COX-2 protein. The level of COX-1 protein is not altered.
Hexahydrocurcumin (7-14 μM; 24 hours) attenuates lipopolysaccharide (LPS)-elicited increase of prostaglandin E
2
(PGE
2
) in murine macrophages (RAW 264.7) in a concentration-dependent manner.
Cell Viability Assay
| Cell Line: | HT-29 cells |
| Concentration: | 0 µM, 5 µM, 10 µM, 25 µM |
| Incubation Time: | 24 hours or 48 hours |
| Result: | Significantly decreased the viability of HT-29 colon cancer cells. |
RT-PCR
| Cell Line: | HT-29 cells |
| Concentration: | 25 µM |
| Incubation Time: | 24 hours |
| Result: | Combined with 5-fluorouracil (5-FU; 5 µM) markedly reduced the COX-2 expression. |
Western Blot Analysis
| Cell Line: | HT-29 cells |
| Concentration: | 25 µM |
| Incubation Time: | 24 hours |
| Result: | Combined with 5-fluorouracil (5-FU; 5 µM) markedly reduced the COX-2 protein. |
Hexahydrocurcumin (50 mg/kg; oral administration; daily; for 16 weeks; male Wistar rats) treatment significantly reduces the numbers of aberrant crypt foci (ACF) in colon cancer rats. Hexahydrocurcumin also markedly decreases COX-2 protein expression. The levels of COX-1 protein is not different from normal rats.
| Animal Model: | Male Wistar rats (100-120 g) injected with dimethylhydrazine (DMH) |
| Dosage: | 50 mg/kg |
| Administration: | Oral administration; daily; for 16 weeks |
| Result: | Significantly reduced the numbers of ACF in colon cancer rats. Also markedly decreased COX-2 protein expression. |
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 |
|---|---|---|---|---|---|
| 2025/12/22 | HY-N0929 | 六氢姜黄素 Hexahydrocurcumin | 36062-05-2 | 1 mg | 1048元 |
| 2025/12/22 | HY-N0929 | 六氢姜黄素 Hexahydrocurcumin | 36062-05-2 | 5mg | 2880元 |