555-66-8
6-Shogaol
CAS: 555-66-8
Molecular Formula: C17H24O3
555-66-8 - Names and Identifiers
| 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 |
555-66-8 - Physico-chemical Properties
| 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. |
555-66-8 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| WGK Germany | 3 |
555-66-8 - Reference
| 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. |
555-66-8 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| alkyphenols formed by dehydration of 6-gingerol | ginger is derived from fresh or dried rhizomes of Zingiberaceae, as a seasoning widely used in the world, and in China, Ginger also as a traditional Chinese medicine prescription to treat many diseases such as: Fever, blood stasis, enteritis. According to the traditional Chinese medicine theory, ginger flavor is warm, longer than the divergence of wind and cold, phlegm and cough, but also warm, anti-vomiting, detoxification; Ginger heat, strong xinlie, longer than warm back to Yang, the patient also received warm lung-resolving drink. In recent years, ginger has attracted more and more attention due to its new biological activities. Gingerol is the most abundant bioactive component in ginger, but Gingerol is very unstable. During the storage of ginger, it will dehydrate to produce a large amount of gingerol. At present, it is found that there are more than 100 kinds of chemical components in ginger, mainly including gingerol and other three categories: ① volatile oil: the main components are monoterpenes, such as α-pinene, Β-sesquiterpenoids and other 37 components. ② gingerols: can be divided into ginger phenols, Ginger phenols, Ginger ketones, Ginger ketones, etc., the main spicy ingredients are 6-ginger phenol, 8-ginger phenol, 10-ginger phenol, 6-ginger diketone and 6-ginger phenol, 8-ginger phenol, 10-ginger phenol and other 7 kinds. ③ diphenylheptane: includes cyclic diphenylheptanes and linear diphenylheptanes. In dried ginger, the ratio of 6-gingerol to Gingerol is about 1:1. 6-gingerol has anti-inflammatory, anti-atherosclerosis, treatment of gastric ulcer, cardiovascular disease, senile dementia, recovery of motor function caused by bone marrow injury, anti-liver Virus and other biological activities. 6-gingerol (6-Shogaol,6S) is the main component of ginger and dried ginger 6-gingerol dehydration formation of Alkylphenol compounds, which has good anti-tumor and related pharmacological activity, such as antioxidant, anti-inflammatory, anti-vomiting, protection of spinal cord injury and other activities. 6s showed good activity against the proliferation of solid tumor cells, but the inhibitory effect of 6s and its analogs on non-solid tumor cells (such as leukemia) was rarely reported; its activation of Toll-like receptor signaling pathway may become a new direction in tumor immunotherapy. Studies have found that in human umbilical vein endothelial cells, 6-gingerol can protect endothelial cells from damage by inhibiting the release of LOX-1 caused by oxidized low density lipoprotein. 6-gingerol can inhibit the proliferation of VSMCs induced by PDGF in a dose-dependent manner, and 6-gingerol at a concentration as low as 5 μmol /L can significantly inhibit the proliferation of VSMCs induced by PDGF, the inhibitory effect increased with the increase of concentration, and the proliferation of VSMCs was still significantly inhibited at the concentration of 20 μmol /L. At the same time, 6-gingerol can down-regulate the expression of TLR4 induced by PDGF in a dose-dependent manner, and has a significant inhibitory effect on the expression of TLR4 induced by LPS, it is suggested that 6-gingerol plays an important role in counteracting the inflammatory reaction of VMSC. In addition, the nuclear transcription factor NF-κB is the key factor of TLR4 downstream mediated inflammatory response, the study found that PDGF induced proliferation and simple application of LPS activated TLR4, can significantly up-regulate the expression of NF-κB in VSMCs. 6-gingerol inhibited the expression of NF-κB induced by PDGF and decreased the expression of NF-κB induced by LPS in a dose-dependent manner, it is suggested that 6-gingerol has an inhibitory effect on the activation of TLR4 /NF-κB inflammatory signals during the proliferation of VSMCs. 6-gingerol can significantly inhibit the proliferation of VSMCs, which may be an important mechanism of anti-atherosclerosis. 6-gingerol may inhibit the inflammatory response mediated by TLR4 by down-regulating the TLR4 /NF-κB inflammatory signaling pathway in VSMCs, and ultimately inhibit the proliferation of VSMCs. In conclusion, given the effectiveness, broad spectrum and good safety of 6s anti-tumor, it is expected to provide a new intervention strategy for clinical treatment and prevention of atherosclerosis, and is likely to become a new potential anti-tumor drug. Fig.1 structural formula |
| biological activity | 1. Promoting tumor cell apoptosis 1) regulation of apoptosis-related genes this product can stimulate the production of reactive oxygen species (ROS), release cytochrome C, activate the death protease caspase, cleave DNA, apoptosis was then mediated in COLO205 colon cancer cells by up-regulating the pro-apoptotic proteins Bax and Fax, down-regulating the anti-apoptotic proteins Bcl-2 and Bcl-X(L), and up-regulating the expression of GADD153 in a dose-and time-dependent manner. This product can also significantly induce apoptosis of poorly differentiated and P53 mutant hepatoma cell lines (high expression of drug resistance genes MDR-1 and Bcl-2) through oxidative stress-mediated caspase-dependent pathway, which first induces ROS production, depletion of intracellular glutathione, reduction of mitochondrial membrane potential, and then activation of caspase-3/-7 and degradation of DNA, induced apoptosis. 2) increase the concentration of Ca2 in tumor cells. The study confirmed that the product inhibited the growth of oral cancer cells by increasing the intracellular Ca2 concentration. When the concentration of this product is> μmol · L-1, the concentration of Ca2 is concentration-dependent; In the absence of Ca2 medium, the high Ca2 concentration produced by this product can be eliminated by the endoplasmic reticulum Ca2 pump inhibitor, the Ca2 signal can be blocked by La(3), but not by L-type Ca2 channel blockers. In Ca2-free medium, the high Ca2 concentration caused by this product was not related to protein kinase C activity, but aristolochic acid I, a 20 μmol · L-1 phospholipase A2 inhibitor, inhibited its effect by 82%. Phospholipase C specific inhibitor U731226 can reduce the product induced Ca2 release. In addition, at the concentration of 5~100 μmol · L-1, the effect of killing OC2 cells was concentration dependent. These suggest that the goods to inositol 1,4, 5-triphosphate-dependent manner and toxic carotene-sensitive intracellular calcium release pathway and phospholipase A2 and La(3) A sensitive pathway for the efflux of CA2. 3) irreversible cycle arrest study found that in human colon cancer cell line HCL116 cells, 6-gingerol can down-regulate the cell cycle proteins cdk1, cyclin B and cdc 25C and spindle assembly protein mad2, the expression of cdc 20 and survivin causes irreversible G2/M phase arrest, which plays a role in promoting apoptosis. 2. Autophagy study found that this product can induce non-small lung cancer cell A549 to achieve self-endocytosis by inhibiting AKT/mTOR signaling pathway and eventually lead to death. When pretreated with autophagy inhibitor 3-methyl purine, the anti-proliferative effect mediated by the product was significantly cleared, suggesting that autophagy is the main way to mediate the cell death. At the same time, it was found that the product inhibited A549 cell survival by blocking the activation of serine/threonine kinase and its downstream target (mTOR,FKHR) and GSK-3beta and reducing the expression of mTOR downstream target (p70OS6kinase) and 4E-BP1. Overexpression of AKT significantly reduced the product-mediated cell death, in addition to small fragments of AKT interfering RNA(siRNA) to promote 6s-mediated cell death. Inhibition of tumor cell invasion and metastasis 6-gingerol can inhibit tumor cell invasion and metastasis. The study found that the goods through the regulation of matrix metalloproteinase 9 (MMP-9) and human tissue inhibitor of metalloproteinase 1(TIMP-1) and activation of urokinase-type plasminogen activity, thereby inhibiting liver metastasis. This product inhibits the migration and invasion of cells by inhibiting the migration and invasion of 12-decanoate -13-acetate. When the product was incubated with treated HepG2 cells and Hep3B cells without PMA treatment, the activity of MMP-9 was significantly decreased, while the expression of TIMP-1 was significantly enhanced. Induced microtubule damage study found that 6-gingerol can induce microtubule damage, its mechanism of action is α,β unsaturated double bonds and microtubule thiol binding to produce anti-tumor effect. In addition, this product can reduce the viability of gastric cancer cells, the mechanism is mainly through the damage of microtubules and induced mitotic arrest. Activation of Toll-like receptor 6s can directly inhibit lipopolysaccharide-induced TLR4 polymerization, thereby inhibiting downstream NF-κB and cyclooxygenase-2 activation. In addition, the product inhibits the TRIF-dependent Toll-like receptor pathway by targeting TBK1, which suggests that the product can well activate autoimmunity through Toll-like receptors to produce anti-inflammatory and anti-tumor effects. 6. Other effects it is reported that ginger extract rich in 6-gingerol can inhibit the growth of Helicobacter pylori Cag A, suggesting that this product and its analogs have the effect of preventing gastric cancer. In addition, Nausea and Vomit are very common adverse reactions in cancer patients after chemotherapy, which seriously affect the quality of life of patients. The study found that the goods and its analogs by inhibiting the stomach serotonin receptor 4 and produce anti Nausea, Vomit effect. More importantly, the acute toxicity test in ddY mice and the oral tolerance test in healthy volunteers show that the product has good safety. (2016-05-10) |
| biological activity | Shogaol ([6]-Shogaol) is an active substance isolated from ginger, has a variety of biological activities, including anti-cancer, anti-inflammatory and antioxidant. |
| Use | for content determination/identification/pharmacological experiments. Pharmacological Efficacy: phenolic compounds in ginger have strong antioxidant properties, which will be conducive to anti-carcinogenic and anti-mutation effects. |
Last Update：2024-04-09 20:49:11
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Product Name: 6-Shogaol Visit Supplier Webpage Request for quotationCAS: 555-66-8
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: 6-Shogaol Visit Supplier Webpage Request for quotationCAS: 555-66-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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