5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)-
alpha-ecdysone
CAS: 3604-87-3
Molecular Formula: C27H44O6
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- - Names and Identifiers
| Name | alpha-ecdysone |
| Synonyms | ECDYSONE Ecdysone AI3-44726 CCRIS 6931 BRN 2422986 ALPHA-ECDYSON alpha-Ecdysone ALPHA-ECDYSONE alpha-ecdysone ECDYSONE, ALPHA- ALPHA-ECDYSTERONE 4-08-00-03613 (Beilstein Handbook Reference) (2beta,3beta,5beta,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one 7,(5-ALPHA)-CHOLESTEN-2-BETA, 3-BETA, 14-ALPHA, 22R, 25-PENTOL-6-ONE (2beta,3beta,5beta,9xi,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one 2-beta,3-beta,14,22,25-pentahydroxy-,(20s,22r)-5-beta-cholest-7-en-6-on 2,3,14,22,25-pentahydroxy-,(2-beta,3-beta,5-beta,22r)-cholest-7-en-6-on 5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2-beta,3-beta,5-beta,22R)- (9CI) |
| CAS | 3604-87-3 |
| EINECS | 222-760-4 |
| InChI | InChI=1/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17?,19-,20+,22+,23-,25+,26+,27+/m0/s1 |
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- - Physico-chemical Properties
| Molecular Formula | C27H44O6 |
| Molar Mass | 464.63 |
| Density | 1.0493 (rough estimate) |
| Melting Point | 242°C |
| Boling Point | 488.1°C (rough estimate) |
| Specific Rotation(α) | 20578 +62° |
| Flash Point | 350°C |
| Solubility | chloroform |
| Vapor Presure | 1.26E-18mmHg at 25°C |
| Appearance | Cryst. |
| Color | White to Off-White |
| Merck | 13,3525 |
| BRN | 2422986 |
| pKa | 14.07±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4482 (estimate) |
| Use | Can promote cell growth, stimulate dermal cell division, the human body also has a role in promoting protein synthesis |
| In vivo study | Ecdysone (α-Ecdysone; 6 µg/g/day; SC; for 14 days) evidently impaires kidney function marked by a statistically significant increase in BUN levels and amplifies renal expression of α-SMA in male C57BL/6 mice aged 10 weeks. Ecdysone confers an MR dependent nephropathic effect. |
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | FZ8170000 |
| FLUKA BRAND F CODES | 10 |
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- - Reference
| Reference Show more | 1. Zhou, Jing, et al. "A strategy for rapid discovery of traceable chemical markers in herbal products using MZmine 2 data processing toolbox: A case of Jing Liqueur." Chinese Herbal Medicines (2021). 2. [IF=5.34] Jing Zhang et al."Application of “spider-web” mode in discovery and identification of Q-markers from Xuefu Zhuyu capsule."Phytomedicine. 2020 Oct;77:153273 |
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- - Reference Information
| overview | ecdysterone (ecdysterone,β-ecdysone) is a hormone that regulates insect growth and metabolism and was first studied by entomologists. In 1954, Butenandt et al. isolated 250mg of the original insect metamorphic active substance ecdyone (ecdysone) from 500kg silkworm pupa. Since then, many similar substances have been isolated in many species of plants. It has been found that the distribution of molting in the plant kingdom is not only higher than that in the animal kingdom, but also wider and rich in resources, such as domestic Achyranthes bidentata, Achyranthes bidentata, Mulberry leaf, Prunella vulgaris, Alisma orientalis, Luohan pine, yew, black hair ferns and purple skies all contain their analogs. It is the study of the mechanism of action of ecdysone that makes people realize that steroidal substances play a role by changing genetic activity and affecting the transcription of genetic information. In the following years, the structure of ecdyone was determined. The pharmacological effects of ecdysone, especially ecdysterone, are beginning to attract people's research interest. Research in the past two decades has found that ecdysterone also shows strong pharmacological activity for higher animals. |
| Effect | 1. Promoting the synthesis of nucleic acids and proteins The research on ecdysterone was first about its assimilation. 2. Effects on glucose metabolism The effects of ecdysterone on mammals, including its effects on glucose metabolism, are mediated through the cAMP-protein kinase system. 3. Promoting lipid metabolism The regulation of ecdysterone on lipid metabolism is related to the effect of ecdysterone on cAMP-protein kinase system. 4. Immunomodulatory effects The inhibitory effect of ecdysterone on histamine release from rat peritoneal mast cells may be related to its inhibitory effect on the mobilization of intracellular stored calcium. 5. Effects on the central nervous system ecdysterone, as a hormone regulating insect growth and metabolism, also has a wide range of pharmacological effects on higher animals, with little toxic and side effects, and is widely distributed in the plant kingdom. In-depth study of the pharmacological effects of ecdysterone can not only provide basis for the mechanism of action of many traditional Chinese medicines. |
| preparation | a method for extracting ecdysterone from plants, characterized by the following steps: a. raw materials are crushed, biological enzymes are added to hydrolyze at 40-50 ℃ for 2-3 hours, water is added to heat the temperature to 70-80 ℃, soaking for 1-2 hours, extracting 2-3 times, and filtering to obtain the extract; B the extract is added to ultrafiltration membrane ultrafiltration, the permeate is then added with a nanofiltration membrane for concentration, the concentrated solution is added with an equal volume of ethanol solution for filtration, and then ethyl acetate is added for extraction, the raffinate is added with activated carbon for reflux decolorization, the decolorization solution is filtered and concentrated to alcohol-free crystals, and the crystals are dried to obtain ecdysterone. |
| Biological activity | Ecdysone (α-Ecdysone) is the main steroid hormone in insects and herbs, which can activate mineralocorticoid receptor (MR) and induce apoptosis (apoptosis). Ecdysone plays an important role in coordinating developmental transition and homeostatic sleep regulation through its active metabolite, 20-hydroxyecdysone (Crustecdysone; 20E; HY-N6979). |
| Cell Line: | Inner medullary collecting duct cells (IMCD) IMCD cells |
| Concentration: | 100 nM 10, 100 nM |
| Incubation Time: | For 48 hours For 48 hours |
| Result: | Caused renal tubular cell apoptosis. Induced the expression of a-smooth muscle actin (SMA), a standard mesenchymal marker in a dose dependent fashion. |
| use | can promote cell growth, stimulate dermal cell division, and promote protein synthesis |
Last Update：2024-04-09 19:05:11
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