6-GINGEROL
6-Gingerol
CAS: 23513-14-6
Molecular Formula: C17H26O4
6-GINGEROL - Names and Identifiers
| Name | 6-Gingerol |
| Synonyms | GINGEROL 6-Gingerol 6-GINGEROL GINGEROL [6] [6]-GINGEROL, ZINGIBER OFFICINALE 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 5-HYDROXY-1-(4'-HYDROXY-3'-METHOXYPHENYL)-3-DECANONE 1-(4'-HYDROXY-3'-METHOXYPHENYL)-5-HYDROXY-3-DECANONE (S)-5-HYDROXY-1-(4-HYDROXY-3-METHOXY-PHENYL-3-DECANONE (S)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl-3-decanone (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one (5s)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one |
| CAS | 23513-14-6 |
| EINECS | 607-241-6 |
| InChI | InChI=1/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1 |
| InChIKey | NLDDIKRKFXEWBK-AWEZNQCLSA-N |
6-GINGEROL - Physico-chemical Properties
| Molecular Formula | C17H26O4 |
| Molar Mass | 294.39 |
| Density | 1.083±0.06 g/cm3(Predicted) |
| Melting Point | 31℃ |
| Boling Point | 453.0±35.0 °C(Predicted) |
| Specific Rotation(α) | +26.5 (c, 1 in CHCl3) |
| Flash Point | 159°C |
| Solubility | Soluble in methanol, ethanol, DMSO, slightly soluble in water. |
| Vapor Presure | 5.39E-09mmHg at 25°C |
| Appearance | Oil |
| Color | White to Light yellow |
| pKa | 10.02±0.20(Predicted) |
| Storage Condition | -20°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.522 |
| MDL | MFCD00210507 |
| Physical and Chemical Properties | White waxy solid, soluble in methanol, ethanol, DMSO and other organic solvents, derived from dried ginger, ginger, turmeric. |
6-GINGEROL - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 2811 6.1 / PGIII |
| WGK Germany | 3 |
| RTECS | HE0757000 |
| HS Code | 29145090 |
6-GINGEROL - Reference
| Reference Show more | 1. Li Min, Liu Yuantao, Wang Lei, Wang Shengguang, Zhang Huihui, Shao Zhude, Dai Long, Gao Peng. Comparative Study on the Content of 6-gingerol in Different Wendan Decoction Preparations [J]. Shi Zhen Chinese Medicine (Phase 8):1901-1903. 2. Zhou Quan, Wang Hanxue, Li Suli, et al. Optimization of Extraction Process of Shuxin Tongmai Granules [J]. Chinese Patent Medicine, 2019(10). 3. Luo Guangzhi, Han Xiaochun, Yu Wanchen, et al. Simultaneous Determination of Six Components in Huanglian Decoction by UHPLC-MS/MS [J]. Shi Zhen Guo Yi Guo Yao, 2019(5):1119-1121. 4. Liang Na Sang Ya Xin Zhou Yan Liu Weihua Li Tian Ye Wang Xiang Hong. HPLC-ESI-Q-TOF-MS/MS Analysis of Gingerol Compounds in Dried Ginger [J]. Food Industry Science and Technology 2018 39(09):252-256. 5. Wang Zhirong, Li Zhili, Li Mingyan, et al. Comparison of Main Components in Fujian Fresh Ginger and Dried Ginger. 6. Wu Yichen, Xie Hui, Mao Chunqin, et al. HPLC Fingerprint of Compound Glycyrrhiza Qingyang Mixture [J]. Chinese Patent Medicine, 2019, 041(009):2251-2256. 7. Zhou Ying, Wei Shijing, Ge Yazhong, et al. Changes in the content of bioactive components and their antioxidant activity during the fermentation of ginger enzymes [J]. Food Industry Science and Technology, 2018. 8. Qiao Lifei, Sun Chengtao, Wang Hongyun, et al. Study on the purification process of macroporous resin of Compound Guizhi Decoction [J]. Jiangxi Traditional Chinese Medicine, 2017, 07(v.26; no.303):57-61. 9. Li Huang, Ma Huanghuang, Qiao Lifei, et al. Study on Quality Standard and in Vitro Dissolution of Guizhi Dropping Pills [J]. Chinese Journal of Traditional Chinese Medicine Information, 2017, 024(009):80-83. 10. Shao Zhuying, Pan Jinhuo, Zhang Yuechan, Jiang Zhitao, Wang Xue, Feng Xingyue, wang Jianchun. Protective Effect of 6-Gingerol on Aristolochic Acid A- induced HK-2 Renal Tubular Epithelial Cell Injury [J]. Chinese patent medicine, 2020,42(10):2744-2747. 11. Lily, Chen Yong, Zhang Mengwei, Yan Hongxia, Gao Shouhong, Chen Wansheng. UHPLC-MS/MS Determination of 11 Main Components in Cold Shiyu Lung Decoction, Experience Recipe of New Coronary Pneumonia [J]. Journal of Pharmaceutical Practice, 2021,39(02):148-151 156. 12. Wang Zhirong, Li Zhili, Li Mingyan, Gao Zidan, Wang Baohua, Li Changhong, Li Wenxu. Comparison of Main Components in Fujian Fresh Ginger and Dried Ginger [J]. Chinese patent medicine, 2020,42(08):2230-2236. 13. Liu Jiayao, He Yi, Tian Jinjie, Wang Lisheng, Xie Bo, Ling Jiajun. Establishment of Microdialysis Method for Active Components of Sini Decoction in Blood and Heart [J]. New Chinese Medicine and Clinical Pharmacology, 2020,31(09):1086-1091. 14. Lan Jile, Ruan Yeping, Qiu Luqi. Multi-index Optimization of Extraction Process of Fengyin Decoction Based on BAS-GA-BP Neural Network and Entropy Weight Method [J]. Chinese Journal of Traditional Chinese Medicine, 2020,45(23):5686-5693. 15. Arshad Zahoor, Chao Yang, Yaping Yang, Yingfang Guo, Tao Zhang, Kangfeng Jiang, Shuai Guo, Ganzhen Deng, 6-Gingerol experiments anti-inflammatory effects and protective properties on LTA-induced mastitis, Phytomedicine, Volume 76, 2020, 153248, ISSN 0944-7113, 16. [IF = 2.863] Xue Han et al."6-Gingerol, an active pungent component of ginger, inhibits L-type Ca2 current, contractility, and Ca2 transients in isolated rat ventricular myocytes." Food Sci Nutr. 2019 Apr;7(4):1344-1352 17. [IF = 11.878] Li Xinming et al."A fast and specific fluorescent probe for thioredoxin reductase that works via disulphide bond cleavage." Nat Commun. 2019 Jun;10(1):1-12 18. [IF = 5.81] Cui Lihua et al."Chaihu Guizhi Ganjiang Decoction Ameliorates Pancreatic Fibrosis via JNK/mTOR Signaling Pathway." Front Pharmacol. 2021 Jun;0:1369 19. [IF = 5.396] Xie Xing et al."Influence of Sargassum pallidum and the synergistic interaction mechanism of 6-gingerol and poricoic acid A on inhibiting ovalbumin glycation." Food Funct. 2021 Oct;12(19):9315-9326 20. [IF = 4.268] Arshad Zahoor et al."6-Gingerol exerts anti-inflammatory effects and protective properties on LTA-induced mastitis." Phytomedicine. 2020 Sep;76:153248 21. [IF = 0.986] Ji-le Lan et al."Q-marker Prediction Analysis of Rhubarb in Fengyin Decoction Based on Fingerprint and Network Pharmacology:." Nat Prod Commun. 2021;16(8): 22. [IF = 6.048] Xue Han et al."6-Gingerol results a protective effect against hypoxic through the p38/Nrf2/HO-1 and p38/NF-κB pathway in H9c2 cells." J Nutr Biochem 2022 Mar;:108975 23. [IF = 6.529] Zhe Cheng et al."6-gingerol ameliorates metabolic disorders by inhibiting hypertrophy and hyperplasia of adipocytes in high-fat-diet induced obese mice." Biomed Pharmacother. 2022 Feb;146:112491 24. [IF = 3.765] Liu Miaomaio et al."Inhibition of human ether-à-go-go-related gene k currents expressed in HEK293 cells by three gingerol components from ginger." JOURNAL of PHARMACY AND PHARMACOLOGY. 2022 May;: |
6-GINGEROL - Introduction
Pharmacological effects: It has the effects of dispelling cold and sweating, resolving phlegm and relieving cough, and relieving stomach, relieving vomiting, etc.
Last Update：2022-10-16 17:15:08
6-GINGEROL - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | the content of 6-gingerol (6-gingerol) in gingerol is the highest, accounting for more than 75% of gingerol substances, and its biological activity is also the strongest. 6-Gingerol can stimulate the mucosa and promote the secretion of gastric juice; it can inhibit abnormal fermentation in the intestine and promote gas emissions; it has an exciting effect on the cerebral cortex and vascular movement center, and can improve blood circulation. |
| use | 6-gingerol can stimulate mucosa and promote gastric juice secretion. It can inhibit abnormal fermentation and promote gas emission in intestinal tract. It has exciting effect on cerebral cortex and vascular movement center and can improve blood circulation. Modern medical research has confirmed that 6-gingerol has antibacterial, anti-tumor, antioxidant, anti-inflammatory, anti-platelet and other effects. It also has the effects of strengthening the heart, preventing and treating cardiovascular diseases, anti-coagulation, anti-ulcer, anti-vomiting, anti-halo, and inhibition of prostaglandin synthesis, choleretic, antiseptic and insecticidal, deworming and skin care and beauty. ( )-[6]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. ( )-[6]-Gingerol down regulates p roinflammatory cytokine release by macrophages. ( )-[6]-Gingerol has been shown to inhibit COX-2 expression by blocking the activation of p38 MAP kinase and NF-KB in phorbol ester-stimulated mouse skin. 6-gingerol is a kind of antioxidant activity bioactive compounds, it is an anti-inflammatory and anti-tumor drug. Decreased 6-gingerol regulates macrophage inflammatory cytokine release. Inhibition of COX -2 expression by blocking p38 MAP kinase and NF -κB activity. |
| preparation | CN201210553119.2 provides a simple process, simple operation and high separation efficiency and separation purity from ginger to extract and purify 6-gingerol. Including the following steps: (1) extraction and concentration of gingerol: the sliced ginger is placed in a small multifunctional extraction and concentration tank, and the mass concentration of ethanol with a mass concentration of 80-95% is used at a mass-to-liquid ratio of 1:6-15 at 60-80 ℃ Heat reflux extraction, the extraction time is 2-3 hours each time, each batch of ginger is extracted 2-4 times, and the extraction liquid each time flows into the small multifunctional extraction and concentration tank, ginger extract is obtained by unified concentration; ⑵ Gingerol extraction: the ginger extract is placed in a glass reactor, extracted with ethyl acetate, and the extraction times are 2-4 times, and the extract is combined to obtain the extract; The extract is recovered under reduced pressure by a rotary evaporator to obtain the crude gingerol extract; the volume ratio of the ginger extract to the ethyl acetate is 1:2-4; (3) Silica gel column chromatography: dissolve the crude gingerol extract in ethyl acetate, then add a silica gel sample with 2-4 times the weight of the crude gingerol extract, volatilize the solvent ethyl acetate, and dry the silica gel column; use petroleum ether-ethyl acetate mixed solvent equal degree elution, thin layer chromatography TCL detection, collect the eluent containing 6-gingerol, and use a rotary evaporator to decompress and recover the eluent to obtain 6-gingerol crude; put the crude 6-gingerol on the silica gel column again, and elute, detect, collect, and recover the solvent according to the above method to obtain a relatively pure 6-gingerol; (4) Preparation of HPLC purification: the relatively pure 6-gingerol obtained in the step (3) is dissolved in a methanol-water mixed solvent to prepare HPLC purification, and the methanol-water mixed solvent is used as the flow equality elution to collect the maximum chromatographic peak, place the rotary evaporator to evaporate to a constant weight, that is, high-purity 6-ginger phenol. |
Last Update：2024-04-09 02:00:07
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