(22E)-Ergosta-5,7,22-trien-3-ol
Ergosterol
CAS: 57-87-4
Molecular Formula: C28H44O
(22E)-Ergosta-5,7,22-trien-3-ol - Names and Identifiers
| Name | Ergosterol |
| Synonyms | Ergosterol Provitamin D2 ergosta-5,7,22-trien-3-ol (22E)-Ergosta-5,7,22-trien-3-ol (22E)-ergosta-5,7,22-trien-3-ol (3beta)-Ergosta-5,7,22- trien-3-ol (22E,24R)-Ergosta-5,7,22-trien-3-ol (22E)-Ergosta-5,7,22-trien-3beta-ol (3beta,22E)-ergosta-5,7,22-trien-3-ol Ergosterol (22E)-Ergosta-5,7,22-trien-3β-ol 7,22-trien-3-ol, (3.beta.)-Ergosta-5 delta-5,7,22-ergostatrien-3beta-ol 3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol, Provitamin D2 (3S,9S,10R,13R,17R)-10,13-dimethyl-17-[(E)-1,4,5-trimethylhex-2-enyl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol |
| CAS | 57-87-4 |
| EINECS | 200-352-7 |
| InChI | InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19?,20?,22-,24+,25?,26-,27-,28+/m0/s1 |
| InChIKey | DNVPQKQSNYMLRS-APGDWVJJSA-N |
(22E)-Ergosta-5,7,22-trien-3-ol - Physico-chemical Properties
| Molecular Formula | C28H44O |
| Molar Mass | 396.66 |
| Density | 0.9784 (rough estimate) |
| Melting Point | 156-158°C(lit.) |
| Boling Point | 250 °C (1.3 mmHg) |
| Specific Rotation(α) | -120 º (c=1, CHC13) |
| Flash Point | 216.3°C |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Solubility | Soluble in benzene and chlorine, soluble in ethanol, ether and other organic solvents. Insoluble in water. |
| Vapor Presure | 3.7E-12mmHg at 25°C |
| Appearance | White flake or needle crystal |
| Color | White to off-white |
| Merck | 14,3659 |
| BRN | 2338604 |
| pKa | 14.91±0.70(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable, but may be light or air sensitive. Incompatible with acids, strong oxidizing agents. |
| Sensitive | Light Sensitive |
| Refractive Index | -112.5 ° (C=1, THF) |
| MDL | MFCD00003623 |
| Physical and Chemical Properties | Colorless needle-like or plate-like crystals. Soluble in ethanol, ether, benzene and chloroform, insoluble in water. Ergosterol was dissolved in a solvent such as chloroform, diethyl ether or cyclohexane, and added to a quartz glass flask to prepare vitamin D by ultraviolet irradiation. |
| Use | It is a precursor for the production of vitamin D2 and an intermediate for the production of hormone drugs, which can be used to produce cortisone |
(22E)-Ergosta-5,7,22-trien-3-ol - Risk and Safety
| Risk Codes | R28 - Very Toxic if swallowed R48/20/22 - R40 - Limited evidence of a carcinogenic effect R38 - Irritating to the skin R25 - Toxic if swallowed R67 - Vapors may cause drowsiness and dizziness R36/38 - Irritating to eyes and skin. R22 - Harmful if swallowed R20 - Harmful by inhalation R63 - Possible risk of harm to the unborn child |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 1-3-8-10 |
| HS Code | 29334900 |
| Hazard Class | 6.1 |
| Packing Group | II |
(22E)-Ergosta-5,7,22-trien-3-ol - Upstream Downstream Industry
| Downstream Products | Vitamin D2 |
(22E)-Ergosta-5,7,22-trien-3-ol - Reference
| Reference Show more | 1. Guo, Ning, Wu, Zeyu, Wang, Jiangang, et al. Content analysis of three effective components in Polyporus umbellatus from different producing areas, growing years and harvest periods [J]. Specialty research 2019 41(01):76-81 98. 2. Li Xiu Qing Shu Zhi Heng Ming Gan Liang, etc. Identification and analysis of high ergosterol-producing endophytic fungi from Salvia miltiorrhiza [J]. Pharmaceutical Care and Research 2016 016(006):448-451. 3. Wan Yunlei, Han Hongxia, Li Li et al. Effect of low-frequency magnetic field on ergosterol production by liquid-state fermentation of Monascus purpurea [J]. Food science 2017(10):44-48. 4. Lou Ling, Chen Changbao, Zhang Yue, Wanqian Wang Lin, Wang Shumin. Content analysis of ergosterol and ergosterol in different fermentation products of Phyllanthus emblica [J]. Specialty research 2020 42(04):55-59. 5. Liu Ming, Wang Huisen, Li Shen. Study on quality standard of Chunhua Jiangya tablets [J]. Northwest Pharmaceutical Journal, 2020, v.35(03):9-12. 6. Jindong, Hu Rongfeng, Zhou An, etc. Preparation and quality evaluation of Ganoderma lucidum spore oil self-microemulsion [J]. Journal of Anhui University of Traditional Chinese Medicine, 2017, 036(006):89-92. 7. He Rongjun, Zhou Fei, Zhao Yuejun, et al. Optimization of extraction process and antioxidant activity of total sterols from Ganoderma lucidum [J]. Food and Fermentation Industry, 2013, 39(009):200-204. 8. Hu tangling, Yunyun, Xu Zhiqing, Duan Qiangjun, Shao Jing, Wang Tianming, Wang Changzhong. N-butanol extract of Pulsatilla decoction inhibits cell membrane of Candida albicans [J]. Chinese Journal of Traditional Chinese Medicine, 2017,42(16):3185-3190. 9. Dong Yu, Yang Zi, Jia Mengqi, etc. Comprehensive extraction process of effective components from Monascus waste residue [J]. Science and Technology of food industry, 2018, 039(003):158-166. 10. Ang Li, Wei-Yin Xu, Shuangshuang mu, et al. Studies on Pharmacognosy of pear-shaped puffiness fungus [J]. Shi Zhen, National Medicine, 2018, 29(3):611-613. 11. Xu Wei-Yin, Li Ang, Hu DE, et al. Studies on Pharmacognosy of medicinal fungus Nitraria lobata [J]. China edible fungi, 2018, 037(004):47-51. 12. Fan Xiuzhi, Yin Chaomin, Jin Weiling, etc. Optimization of solid fermentation medium and fermentation characteristics of ochratoxin mushroom [J]. Journal of edible fungi, 2018, v.25(04):39-46. 13. Zeng Hui, Zeng Zhiheng, Shu Lili, etc. Determination of relative mycelial mass of Agaricus bisporus W192 by chitin and ergosterol [J]. Journal of edible fungi, 2018, 25(03):40-45. 14. Zheng Shijie, Zhang Rui, Poplar de, etc. Determination of ergocalciferol in Lentinus edodes and its transmission mechanism in human body [J]. Chinese Journal of Bacteriology, 2019, 38(5). 15. Li Yuheng, Sun Xiaodong, Liu runpu, etc. Determination of ergosterol in red yeast rice by HPLC [J]. Chinese condiment, 2019, 044(010):129-131. 16. Luo Jingyan, Zhang Xiaoyu, Xu Ruijie, etc. Comparison of ergosterol, cordycepin, adenosine and polysaccharide in cicadae cicadae under different edible methods [J]. Journal of Anhui Agricultural University, 2018, v.45;No.163(03):11-16. 17. Wang Liying, Hu de, Tang Lei et al. Simultaneous determination of ergosterol and ergosterol in Inonotus obliquus by dual-wavelength HPLC [J]. Pharmaceutical research 2017 36(009):509-511. 18. Yang Xiu-Lu, Meng Jia-Qi, Li Ting et al. Determination of ergosterol and ergosterol in fruiting body and liquid-fermented mycelia of Mevo by dual-wavelength HPLC [J]. Chinese edible fungi 2018(5):57-61. 19. Zhang Xuening, Zhong chengzan, Yang Ming, etc. Establishment of quality control method in production process of jinshuibao capsules [J]. Chinese Journal of Experimental prescriptions, 2020(4). 20. Dong Shujia, Qin, Wei, Shuai, Liu, canzhen, et al. Effect of low nitrogen on ester synthesis in fermentation of Saccharomyces cerevisiae [J]. China brewing 2018 037(001):149-154. 21. Fu tiokun, Zhou Wei, Xia Wen, etc. Study on extraction technology of three main sterols from pitaya stem [J]. Journal of Tropical Agriculture Sciences, 2019, v.39;No.268(12):46-54. 22. Lu Simin, He Xiaobing, Zhang Liting, Ding Hongyan, Qi Yi, Wu tie. Study on the effect of acid leaching high pressure method on the changes of three main components in Ganoderma lucidum spores [J]. Grain and Oil food science and technology, 2019,27(06):93-97. 23. Sun Zhishuang, Jiang Xiaotian. Simultaneous determination of cordycepin, adenosine and ergosterol in Cordyceps militaris by HPLC [J]. Food Research and Development, 2020,41(19):173-176. 24. Lou Ling, Chen Changbao, Zhang Yue, Wan Qianlin, Wang Huan, Wang Shumin. Content analysis of ergosterol and ergosterol in different fermentation products of Phyllanthus emblica [J]. Specialty research, 2020,42(04):55-59. 25. Lou Ling, Chen Changbao, Zhang Yue, Wan Qianlin, Wang Huan, Wang Shumin. Content analysis of ergosterol and ergosterol in different fermentation products of Phyllanthus emblica [J]. Specialty research, 2020,42(04):55-59. 26. Fan Xiuzhi, Yao Fen, Yin Chaomin, Shi Defang, Gao Hong. Exogenous synthesis of ergosterol from Agaricus blazei Murill [J]. Modern food science and technology, 2021,37(01):65-72. 27. Zongzhe et al. [IF = 5.279]. "Deoxynivalenol in Fusarium graminearum: Evaluation of cyanproazole stereosomes In Vitro and In Planta." J Agr Food Chem. 2021;69(34):9735-9742 28. [IF = 4.411] Zhixin Wang et al."Rapid Characterization of Chemical Components in Edible Mushroom Sparassis crispa by UPLC-Orbitrap MS Analysis and Potential Inhibitory Effects on Allergic Rhinitis."Molecules. 2019 Jan;24(16):3014 29. [IF=7.514] Simin Feng et al."Simultaneous analysis of free phytosterols and phytosterol glycosides in rice bran by SPE/GC-MS."Food Chem. 2022 Sep;387:132742 30. [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 |
(22E)-Ergosta-5,7,22-trien-3-ol - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | the chemical name of ergosterol is 24 β-methyl cholesterol -5, 7-en-3β-hydroxy, also known as ergosterol, white or colorless bright small leaf crystal or white crystalline powder. Ergosterol not only has a unique physiological role, but also is widely used in drug development. As an important component of fungal cell membrane, ergosterol has stable structure and strong specificity. It is more representative than glucosamine for the determination of biomass, the biomass of the fungus can therefore be measured by measuring the content of ergosterol. |
| purpose | vitamin D2. is a precursor for the production of vitamin D2, is also an intermediate for the production of hormone drugs, can be used to produce cortisone vitamin D2 biological precursors, it is found in the cell membranes of fungi and some protists such as trypanosomes. Ergosterol is useful in the functional studies of antifungal drugs such as amphotericin B and its analogs and in the studies of ergosterol biosynthetic pathways in various fungi. |
| production method | with the preparation of yeast raw material paste, take dry yeast powder through 60-80 mesh sieve, add 3 times the amount of 82%-84% ethanol extraction 18-24H, at 70 ℃ for 3H, constant stirring, let cool to below 30 ℃, filter, filter residue extraction 2 times, pull out ethanol, combined extract, 70 ° C vacuum concentration, concentration time is not more than 24h, the paste. The residue was used to extract ribonucleic acid and yeast polysaccharide. Dry yeast or Geotrichum [ethanol] → [first 68-70 ℃, after 30 deg C below] extract [70 deg C concentration] → paste ergosterol crude preparation of paste paste add 5%-10% of water, add 3-5 times the amount of ether, vigorously stirred 2-3H, after standing for 16-20h, the middle and lower layers of liquid were discarded, and the upper layer of ether liquid was placed in -5 ℃ refrigerator for 20-24H to precipitate ergosterol crystals. Paste [ether] → ether solution in upper layer [-5 ℃]→ crude ergosterol [20-24H]. extracted from yeast that synthesizes the product from glucose. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:51
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