Diosgenin
diosgenin
CAS: 512-04-9
Molecular Formula: C27H42O3
Diosgenin - Names and Identifiers
| Name | diosgenin |
| Synonyms | Diosgemom Nitogenin diosgenin DIOCTYLMALONATE spirost-5-en-3-ol 5-22-Spirosten-3-ol 5-25D-Spirosten-3-ol 25d-Spirost-5-en-3b-ol 20F,22F-Spirosten-3-ol (3beta,25R)-spirost-5-en-3-ol 22alpha-Spirost-5-en-3beta-ol (20R,25R)-spirost-5-en-3-beta-ol DIOSGENIN (3B-HYDROXY-5A-SPIROSCENE) (3beta,8xi,9xi,14xi,16xi,17xi,25R)-spirost-5-en-3-ol (8xi,9xi,10xi,13xi,14xi,16xi,17xi,25R)-spirost-5-en-3-ol |
| CAS | 512-04-9 |
| EINECS | 208-134-3 |
| InChI | InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20?,21?,22?,23?,24?,25+,26+,27-/m1/s1 |
Diosgenin - Physico-chemical Properties
| Molecular Formula | C27H42O3 |
| Molar Mass | 414.63 |
| Density | 1.0483 (rough estimate) |
| Melting Point | 205-208°C |
| Boling Point | 473.46°C (rough estimate) |
| Specific Rotation(α) | D25 -129° (c = 1.4 in CHCl3) |
| Flash Point | 272.6°C |
| Water Solubility | Soluble in chloroform (50 mg/ml), ethanol (83 mg/ml at 25°C), water (<1 mg/ml at 25°C), DMSO (<1 mg/ml at 25°C), and methanol. |
| Solubility | Easily soluble in gasoline, ethanol, chloroform and other organic solvents, insoluble in water |
| Vapor Presure | 2.59E-13mmHg at 25°C |
| Appearance | white to yellowish flake or needle-like crystals |
| Color | White to Pale Yellow |
| Merck | 14,3295 |
| BRN | 94582 |
| pKa | 15.02±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4700 (estimate) |
| MDL | MFCD00016887 |
| Physical and Chemical Properties | Diosgenin is a flake or needle-like crystal. Melting Point 204-207 °c. Soluble in gasoline, ethanol, chloroform and other organic solvents, insoluble in water. Diosgenin in yam mucus, is an important raw material for medicine, medicine is known as the gold. Diosgenin is transformed into diosgenin after removing glycosyl by fermentation, and its anti-inflammatory, serum cholesterol lowering, gastrointestinal function improving and serum antibody IgG secreting ability can be greatly improved. |
| Use | Is the precursor of the synthesis of steroid hormone drugs, for the synthesis of hydrocortisone, prednisone, norethisterone, easy, dexamethasone and other types of steroid drugs |
Diosgenin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - 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. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | WH1450000 |
| HS Code | 29329990 |
Diosgenin - Reference
| Reference Show more | 1. Zhao Lirong, Luo Han, Xiang Yinglong, et al. Optimization of microwave-assisted extraction of total saponins from Rhizoma polygonati by Box-Benhken response surface methodology [J]. Chinese modern traditional Chinese medicine 2018 20(008):1010-1015. 2. Yang Nan-Nan Li Hui, Wu Yan, Zhang Xiaomei, Xu Zhenghong, Shi Jinsong. Optimization of fermentation process of Gibberella intermedia WX12 producing specific glycosidase [J]. Journal of Food and Biotechnology, 2016, 35(10):1028-1034. 3. Yuan Zhiying, Luo Linming, Chen Naihong, etc. Analysis of chemical constituents of Lily bulbus and study on its anti-tumor activity of diosgenin based on UPLC-Q-TOF-MS method [J]. Natural product research and development, 2019, 31(05):808-813. 4. Li Hui, Zhang Jiajia, Liang Jingyi, etc. Cleaner production process of diosgenin from Dioscorea zingiberensis based on enzymatic assisted extraction and microwave acidolysis [J]. Food Science, 2012, 033(020):94-98. 5. Yang Zhao, Hexin Zeng, Zhiqiang Cheng, et al. Study on preparation and quality control of Tribulus terrestris [J]. Shi Zhen, National Medicine, 2019, v.30;No.288(08):98-100. 6. Sun Rui, cow Jie, Cao Fang, etc. Intervention mechanism of diosgenin on human embryonic lung fibroblasts induced by LPS [J]. Global traditional Chinese medicine, 2019, 012(007):988-993. 7. Chen Zhenxing, Zhao Ruizhi. Sensitizing effect of diosgenin on apoptosis of drug-resistant uterine sarcoma MES-SA/MX2 cells induced by mitoxantrone [J]. Chinese Pharmaceutical Journal, 2017,52(24):2157-2160. 8. Hu Jiali, Liu Lin, Li Zhong, etc. Correlation between active ingredient content and color during fermentation of Polygonatum sibiricum [J]. Chinese Journal of Experimental prescriptions, 2020, 3 (15). 9. Yang Yali, Liu Jia, Zhang Peng et al. Analysis of dioscin and sapogenin contents in different parts of four Rhizoma Paridis [J]. Shi Zhen, Chinese medicine 2016(5):1035-1038. 10. Zhang Zerui, Huang Shen, Liu Jingjing, et al. The main nutritional components of Polygonatum sibiricum and Polygonatum sibiricum flower [J]. Chinese Journal of Traditional Chinese Medicine, 2020, v.45(06):123-127. 11. Shihong Huiyuan Guangwei Liao Zhengrui et al. Effects of different strains on nutritional value and antioxidant activity of Moringa oleifera leaf powder [J]. Science and Technology of Food Industry 2019 040(009):91-97 104. 12. Zhou Xiao, Li Xiaolin, Zhou Junbo, Zhang Xiaofei, Guo Dongyan, Cheng Jiangxue, Shi Runjun, Shi Xinhong, Jia Xiaobin. Effect of particle design on pharmacokinetics of Shenling Baizhu powder in rats [J]. Chinese herbal medicine, 2020,51(19):4925-4933. 13. Jia-Li Hu. Study on fermentation technology of Monascus and Polygonatum sibiricum and its immunomodulatory and hypolipidemic effects [D]. Guangdong Pharmaceutical University, 2020. 14. Li Hui-min, Zheng Tao, Zeng Yi-Qiong, Fan Yu-Bing, Li Wei-zhen, Yan Jian-ye, Zhao Liping, Zheng Hui, Yang Yong. Comprehensive optimization of modification process of Polygonatum odoratum powder by AHP-CRITIC weight analysis [J]. Food and Fermentation Industry, 2021,47(05):138-146. 15. Wang, Peng, et al. "Conversion of steroid saponins into diosgenin by catalytic hydrolysis using acid-functionalized ionic liquid under microwave irradiation." Journal of cleaner production 79 (2014): 265-270.https://doi.org/10.1016/j.jclepro.2014.05.041 16. [IF=9.297] Peng Wang et al."Conversion of steroid saponins into diosgenin by catalytic hydrolysis using acid-functionalized ionic liquid under microwave irradiation."J Clean Prod. 2014 Sep;79:265 17. [IF=5.64] Wu Dousheng et al."Oleanolic Acid Induces the Type III Secretion System of Ralstonia solanacearum."Front Microbiol. 2015 Dec;0:1466 18. [IF=4.759] Mengshun Liu et al."Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: Finding anti-enterovirus 71 agents from Anemarrhena asphodeloides."J Chromatogr A. 2014 Nov;1368:116 19. [IF=2.998] Lei Lei et al."Preparation of diosgenin from Dioscorea zingiberensis C. H. Wright by stepwise biocatalysis-foam separation-preparative high-performance liquid chromatography (P-HPLC)."Eur Food Res Technol. 2018 Aug;244(8):1447-1452 20. [IF=0.533] P Wang et al."Ionic Liquid-Based Ultrasonic/Microwave-Assisted Extraction of Steroidal Saponins from Dioscorea zingiberensis C. H. Wright."Trop J Pharm Res. 2014 Sep;13(8):1339-1345 21. [IF=5.923] Lixiu Hou et al."Genome-Wide Identification of CYP72A Gene Family and Expression Patterns Related to Jasmonic Acid Treatment and Steroidal Saponin Accumulation in Dioscorea zingiberensis."Int J Mol Sci. 2021 Jan;22(20):10953 22. [IF=5.275] Liangqun Li et al."Microbial transformation of diosgenin to diosgenone by Wickerhamomyces anomalus JQ-1 obtained from Naxi traditional Jiu Qu."Bioorg Chem. 2020 Jan;95:103508 23. [IF=4.242] Shun Zhou et al."Anthelmintic efficacy of 35 herbal medicines against a monogenean parasite, Gyrodactylus kobayashii, infecting goldfish (Carassius auratus)."Aquaculture. 2020 May;521:734992 24. [IF=3.998] Chengfei Zhang et al."Transcriptome analysis of the effect of diosgenin on autoimmune thyroiditis in a rat model."Sci Rep-Uk. 2021 Mar;11(1):1-12 25. [IF=2.289] Zhou Shun et al."Anthelmintic efficacy of natural saponins against Gyrodactylus kobayashii in goldfish (Carassius auratus) and their 3D-QSAR analysis."Parasitol Res. 2021 Mar;120(3):1143-1150 26. [IF=3.645] Shuo Gu et al."Develop a stepwise integrated method to screen biomarkers of Baihe-Dihuang Tang on the treatment of depression in rats applying with composition screened, untargeted and targeted metabolomics analysis."Journal Of Separation Science. 2022 M 27. [IF=5.753] Jianghong Gao et al."Molecular Cloning and Functional Characterization of a Sterol 3-O-Glucosyltransferase Involved in Biosynthesis of Steroidal Saponins in Trigonella foenum-graecum.."Front Plant Sci. 2021 Dec;12:809579-809579 28. [IF=6.417] Chen Zhou et al."22R- but not 22S-hydroxycholesterol is recruited for diosgenin biosynthesis."Plant Journal. 2021 Dec 07 |
Diosgenin - Introduction
Pharmacological effects: Diosgenin is a plant steroid that induces apoptosis in colon cancer cells and osteosarcoma cells, cell cycle arrest and COX activity.
Last Update：2022-10-16 17:25:43
Diosgenin - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | diosgenin (Diosgenin) comes from the rhizome of monocotyledonous herbaceous twining vines of Dioscoreaceae, such as yam, turmeric, diosporin, diosporin, etc. It is an important basic raw material for the production of hydrocortisone, prednisone, norethindrone, dexamethasone and other steroid drugs. |
| pharmacological effects | studies have shown that diosgenin has antioxidant, anti-vascular calcification, anti-tumor, anti-inflammatory, anti-allergic, antiviral and anti-shock effects. |
| use | this product is an important steroidal sapogenin and an important raw material for semi-synthetic steroidal compounds. Diosgenin is subjected to ring-opening, oxidation, hydrolysis and elimination reactions to obtain pregnenone alcohol. After oximation, rearrangement and hydrolysis, dehydroepiandrosterone can be prepared. These intermediates have important value in drug production. diosgenin is the precursor of synthetic steroid hormone drugs, which is used to synthesize hydrocortisone, prednisone, norethisterone, skin ease, dexamethasone and other steroid drugs. A steroid sapogenin, with estrogen activity, can reduce serum cholesterol levels. |
| production method | using chuandi dragon crude drug or turmeric as raw material, obtained by hydrolysis and extraction. |
Last Update：2024-04-09 21:01:54
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