Name | 6-Shogaol |
Synonyms | SHOGAOL 6-SHOGAOL 6-Shagaol 6-Shogaol SHOGAOL, 6- 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one 1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one 4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl) 1-(3-Methoxy-4-hydroxyphenyl)-4-decene-3-one (E)-1-(4-Hydroxy-3-methoxy-phenyl)dec-4-en-3-one (4E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one |
CAS | 555-66-8 |
InChI | InChI=1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ |
InChIKey | OQWKEEOHDMUXEO-BQYQJAHWSA-N |
Molecular Formula | C17H24O3 |
Molar Mass | 276.37 |
Density | 1.0448 g/cm3(Temp: 25 °C) |
Boling Point | 427.5±35.0 °C(Predicted) |
Flash Point | 150.3°C |
Solubility | Insoluble in water and acid, slightly soluble in alkali, easily soluble in various organic substances. |
Vapor Presure | 6.55E-08mmHg at 25°C |
Appearance | Oil |
Color | Colourless to Light Yellow |
BRN | 2056098 |
pKa | 10.01±0.20(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
Refractive Index | 1.521 |
MDL | MFCD01736094 |
Physical and Chemical Properties | Derived from the active ingredients proposed by ginger. |
In vitro study | Shogaol ([6]-Shogaol) has anticancer activity against several cell lines. Shogaol ([6]-Shogaol) is identified to be cytotoxic in various cell lines, with KB (IC 50 =7.4±2.2 μM) and HL60 (IC 50 =7.9±2.0 μM) cells most susceptible to 6-shogaol. 6-shogaol (IC 50 =8 μM) has much stronger growth inhibitory effects than 6-gingerol (IC 50 =150 μM) on HCT-116 human colon cancer cells. Shogaol ([6]-Shogaol) stimulates phosphorylations of mitogen-activated protein kinases (MAPKs) such as ERK, JNK, and p38. Moreover, the 6-shogaol-induced expressions of Nrf2 and HO-1 are attenuated by treatments of SB202190 (a p38 specific inhibitor) and LY294002 (an Akt specific inhibitor). |
In vivo study | The Shogaol ([6]-Shogaol) decreases the diethylnitrosamine (DEN)-mediated elevations of serum aspartate transaminase and alanine transaminase as well as the DEN-induced hepatic lipid peroxidation. Inductions of Nrf2 and HO-1 by 6-shogaol are also confirmed in the mice. The administration of Shogaol ([6]-Shogaol) to the mice also restores the DEN-reduced activity and protein expression of hepatic antioxidant enzymes such as superoxide dismutase, glutathione peroxidase and catalase. |
Hazard Symbols | Xn - Harmful |
Risk Codes | 22 - Harmful if swallowed |
WGK Germany | 3 |
Reference Show more | 1. Wang Yufeng, Chen Chao, Yang Yinxue et al. Effects of 6-gingerol on h_2o_2-induced oxidative damage of NCM460 and HCT116 [J]. Modern food technology 2017 v.33;No.220(12):6-15. 2. Wang Yufeng, Liu Xu, Chen Chao et al. Effects of 6-gingerol on Keap1/Nrf2 pathway and downstream gene expression in colorectal cancer cells [J]. Journal of Ningxia Medical University 2017 039(010):1127-1132. 3. Wang Yufeng, Chen Chao, Yang Chun, Li Hai, Yang Yinxue. Effects of 6-gingerol on apoptosis and expression of Bax, BCL2, Caspase3 and PARP1 in human colorectal cancer cells [J]. Modern Food Science and Technology 2017 33(11):7-15. 4. Liang Na Sangya new Zhou Yan Liu Wei Hua Li Tian Ye Wang Xiang Hong. Analysis of gingerols in dried ginger by HPLC-ESI-Q-TOF-MS/MS [J]. Science and Technology of food industry, 2018, 39(09):252-256. |