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7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE

20-Hydroxyecdysone

CAS: 5289-74-7

Molecular Formula: C27H44O7

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  5. 7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Names and Identifiers

Name 20-Hydroxyecdysone
Synonyms ecdysterone
Beta Ecdysone
BETA-ECDYSONE
Hydroxyecdysone
Beta Ecdysterone
beta-Ecdysterone
BETA-ECDYSTERONE
20-Hydroxyecdysone
2b,3b,14a,20b,22,25-hexahydroxycholest-7-en-6-one
2B,3B,14A,20,22[R],25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
BETA-ECDYSONE,2,3,14,20,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
2BETA,3BETA,14ALPHA,20BETA,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE
(2beta,3beta,5beta,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
(2beta,3beta,9xi,17xi,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
(2beta,3beta,5beta,20S,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
(2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-TRIHYDROXY-10,13-DIMETHYL-17-((1R,2R)-1,2,5-TRIHYDROXY-1,5-DIMETHYL-HEXYL)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-6-ONE
CAS 5289-74-7
EINECS 811-097-1
InChI InChI=1/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15?,17?,19-,20+,21?,22-,24-,25-,26-,27-/m1/s1
InChIKey NKDFYOWSKOHCCO-YPVLXUMRSA-N

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Physico-chemical Properties

Molecular FormulaC27H44O7
Molar Mass480.64
Density1.0760 (rough estimate)
Melting Point242-244°C
Boling Point498.63°C (rough estimate)
Specific Rotation(α)+61.8 (CHCl3)
Flash Point392.3°C
Solubility Soluble in methanol, DMSO, insoluble in petroleum ether.
Vapor Presure8.7E-23mmHg at 25°C
AppearanceWhite needle crystal
Colorwhite
Merck13,3525
BRN1917578
pKa14.13±0.70(Predicted)
Storage ConditionSealed in dry,Store in freezer, under -20°C
Refractive Index1.5800 (estimate)
MDLMFCD00036740
Physical and Chemical PropertiesWhite crystalline powder, soluble in ethanol, slightly soluble in acetone, slightly soluble in hot water, ethyl acetate, chloroform, almost insoluble in ether, derived from the leakage of Lu, Achyranthes bidentata, Pearl Dew grass Cyanotis,arachnoidea, brazilian ginseng (Pfaffia glomerata).

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
S36 - Wear suitable protective clothing.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany2
RTECSFZ8060000
FLUKA BRAND F CODES10
HS Code29372900

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Reference

Reference
Show more
1. Che Qitao, Yang Huixin, Wang Lili et al. Quality Analysis of Achyranthes bidentata in different harvest time [J]. World Science and Technology-modernization of traditional Chinese medicine 2019(12).
2. Wang Xiaoxi, Zhao Guiying, Yang Hang, etc. Effects of ecdysone and valmin on gene expression of chitin synthase B in armyworm [J]. Chinese Journal of Applied Entomology, 2019(5).
3. Liu Zhichong, Sun Longsheng, Yang Jiawei, etc. Effects of dietary β-ecdysone on growth performance of Macrobrachium rosenbergii. Feed and animal husbandry.
4. LV Zihao, Wang Chunyan, Lin Tong. Temporal and spatial dynamics of neutral endopeptidase gene expression in the yellow wild borer [J]. Jiangsu Journal of Agricultural Sciences, 2019.
5. LV Zihao, Li Zhixing, Lin Tong. Identification and expression analysis of ecdysone receptor gene HvEcR of yellow borer [J]. Northwest Journal of Agricultural Sciences, 2019, 028(007):1187-1194.
6. Liu Ming, Wang Huisen, GE Wenjing, et al. Optimization of water decoction process of Chunhua hypotensive tablets by multi-index orthogonal test [J]. Chinese Medicine Guide, 2020, v.26;No.350(04):20-22 27.
7. Huang Hui, Wang Xiaoqin, Du Yue et al. Simultaneous determination of six components in Flos crenulae by HPLC [J]. Journal of Pharmaceutical Analysis, 2017, 037(006):956-961.
8. Yan: Yu, Zhang: Yu. Simultaneous determination of five components in jinguolan by HPLC-ESI-MS/MS [J]. Chinese herbal medicines, 2017, 40(002):395-398.
9. Zhang Xiaoyu, Li Jia. Simultaneous determination of seven effective components in the wind of gold thread by HPLC-ESI-MS/MS [J]. Chinese Journal of Traditional Chinese Medicine, 2017,32(06):2762-2764.
10. Fan xiaulong, Chen Ran, Wu Wanqin, Liu Guoyan, Huang Kun, Jiang Feng. Determination of 20 functional components in food by liquid chromatography tandem mass spectrometry [J]. Food and machinery, 2021,37(01):86-93 98.
11. Li, Zhixing, et al. "Cloning, Expression Analysis, 20-hydroxyecdysone Induction, and RNA Interference Study of Autophagy-Related Gene 8 from Heortia vitessoides Moore." Insections 11.4 (2020): 245.https://doi.org/10.3390/insects11040245
12. Wang, Chun-Yan, et al. "Chitin deacetylase 1 and 2 are indispensable for larval-pupal and pupal-adult molts in Heortia vitessoides (Lepidoptera: Crambidae)." Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology 237 (2019): 110
13. Zhang, Jing, et al. "Application of “spider-web” mode in discovery and identification of Q-markers from Xuefu Zhuyu capsule." Phytomedicine 77 (2020): 153273.https://doi.org/10.1016/j.phymed.2020.153273
14. [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
15. [IF=3.935] Zhengchao Ji et al."Global identification and quantitative analysis of representative components of Xin-Nao-Kang Capsule, a traditional Chinese medicinal formula, by UHPLC-Q-TOF-MS and UHPLC-TQ-MS."J Pharmaceut Biomed. 2021 May;198:114002
16. [IF=2.769] Zhixing Li et al."Cloning, Expression Analysis, 20-Hydroxyecdysone Induction, and RNA Interference Study of Autophagy-Related Gene 8 from Heortia vitessoides Moore."Insects. 2020 Apr;11(4):245
17. [IF=2.231] Chun-Yan Wang et al."Chitin deacetylase 1 and 2 are indispensable for larval-pupal and pupal-adult molts in Heortia vitessoides (Lepidoptera: Crambidae)."Comp Biochem Phys B. 2019 Nov;237:110325
18. [IF=1.902] Ting Zhang et al."The influence of essential oils from ZhaLi NuSi Prescription on the pharmacokinetics of its non-volatile components in normal rats."Biomedical Chromatography. 2021 Oct 21
19. [IF=1.698] Zhixing Li et al."RNA interference of eclosion hormone gene reveals its roles in the control of ecdysis behavior in Heortia vitessoides Moore."Arch Insect Biochem. 2020 Sep;105(1):e21726

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Introduction

Pharmacological effects: It can promote the synthesis of colloidal protein, anti-arrhythmia, and anti-fatigue; promote cell growth, stimulate dermal cell division, and eliminate cholesterol in the body; lower blood lipids, inhibit blood sugar rise; clear channels and activate collaterals, dehumidification and analgesia, etc. Physiological activity.
Last Update:2022-10-16 17:25:55

7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE - Reference Information

overview ecdysone acts on the human body to promote protein synthesis, eliminate cholesterol in the body, lower blood lipids, inhibit blood sugar rise and other physiological activities, folk used for rheumatoid arthritis. In the sericulture industry, it is used to shorten the age of silkworm and promote silkworms; in the breeding industry, the breeding of prawns and crabs is also widely used; in cosmetics, ecdysone is also used as a special additive; Ecdysone is added to cosmetics to prevent dry skin and make skin more tender. Ecdysone can affect the entire development stage of insects from hatching larvae to adults, so it controls or kills agricultural pests. It has been developed and applied as the third generation pesticide; ecdysone also has certain effects on the physiological process of crops, and has good development and application prospects in crop yield additives.
properties light yellow crystalline powder, odorless, hygroscopic, and gradually darker after light.
Ingredients Ecdysone or ecdysteroid hormones and ecdysteroids are steroid hormones of arthropods that participate in the regulation of molting, development, and to a lesser extent affect reproduction. Ecdysone includes ecdysone, 20-hydroxyecdysone, 2-deoxyecdysone, etc. These compounds are usually converted from food-borne cholesterol and are catalyzed by enzymes of the Halloween gene family in cytochrome P450. Many plants often contain plant ecdysteroids, which act as toxins or antifeedants to combat herbivorous insects.
application ecdysone can promote gum protein synthesis, anti-arrhythmia and anti-fatigue on human body. Promote cell growth, stimulate dermal cell division, and eliminate cholesterol in the body; Lowering blood lipid and inhibiting blood sugar rise; It has physiological activities such as dredging meridians and activating collaterals, dehumidification and analgesia. It is a natural anti-cancer preparation. Since its inception in 1976, ecdystic hormone of deusis, indefinite tablets, injections and ointments have been developed. Folk is used for rheumatoid arthritis. It has a good effect in the treatment of rheumatism and arthritis patients with different symptoms. Its effective ingredient 20-hydroxyecdysterone has been proved by clinical studies to have a direct hypoglycemic effect, and the total effective rate for type 2 diabetes is 84%. It is particularly obvious to improve the symptoms of "three more and one less" in diabetic patients.
use ecdysone is used to shorten the age of silkworm, neatly clustered, and promote silking and cocoon formation. Hormones; High-grade cosmetics; Health care products.
β-ecdysone has the effects of promoting gum protein synthesis, anti-arrhythmia and anti-fatigue.
it plays a key role in insect growth, development, cell expansion and apoptosis, and regulates molting and metamorphosis by regulating gene expression.
Last Update:2024-04-09 21:21:28
7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE
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View History
7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE
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