20-Hydroxyecdysone

• CAT Number: R016187
• CAS Number: 5289-74-7
• Molecular Formula: C27H44O7
• Molecular Weight: 480.642
• Purity: ≥95%
• Storage: 3 years -20C powder
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• InChI: InChI=1S/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+/m0/s1
• InChIKey: NKDFYOWSKOHCCO-YPVLXUMRSA-N
• SMILES: CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O

Ecdysteroid, extracted from plants of the Rhaponticum genus, Compositae.It is an insect growth and moulting stimulating hormone. It has anabolic effect in mammals without androgenic activity.

Reference

1:Effects of juvenile hormone analogue (methoprene) and 20-hydroxyecdysone on reproduction in Polygonia c-aureum (Lepidoptera: Nymphalidae) in relation to adult diapause. Hiroyoshi S, Reddy GVP, Mitsuhashi J.J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2017 May 11. doi: 10.1007/s00359-017-1179-3. [Epub ahead of print] PMID: 28497253 2:20-hydroxyecdysone positively regulates the transcription of the antimicrobial peptide, lebocin, via BmEts and BmBR-C Z4 in the midgut of Bombyx mori during metamorphosis. Mai T, Chen S, Lin X, Zhang X, Zou X, Feng Q, Zheng S.Dev Comp Immunol. 2017 Apr 6;74:10-18. doi: 10.1016/j.dci.2017.04.002. [Epub ahead of print] PMID: 28390932 3:20-Hydroxyecdysone activates PGRP-SA mediated immune response in Locusta migratoria. Han P, Han J, Fan J, Zhang M, Ma E, Li S, Fan R, Zhang J.Dev Comp Immunol. 2017 Jul;72:128-139. doi: 10.1016/j.dci.2017.02.021. Epub 2017 Feb 27. PMID: 28254619 4:20-Hydroxyecdysone from Dacrycarpus imbricatus bark inhibits the proliferation of acute myeloid leukemia cells. Thuy TT, Tam NT, Anh NT, Hau DV, Phong DT, Thang LQ, Adorisio S, Van Sung T, Delfino DV.Asian Pac J Trop Med. 2017 Feb;10(2):157-159. doi: 10.1016/j.apjtm.2017.01.009. Epub 2017 Jan 21. PMID: 28237481 Free Article5:20-hydroxyecdysone enhances the expression of the chitinase 5 via Broad-Complex Zinc-Finger 4 during metamorphosis in silkworm, Bombyx mori. Zhang X, Zheng S.Insect Mol Biol. 2017 Apr;26(2):243-253. doi: 10.1111/imb.12288. Epub 2016 Dec 29. PMID: 28032930 6:Effect of 20-Hydroxyecdysone on Proteolytic Regulation in Skeletal Muscle Atrophy. Hirunsai M, Yimlamai T, Suksamrarn A.In Vivo. 2016 11-12;30(6):869-877. PMID: 27815474 7:The effect of 20-hydroxyecdysone on the susceptibility of Escherichia coli to different antibiotics. Smirnova G, Bezmaternykh K, Oktyabrsky ON.J Appl Microbiol. 2016 Dec;121(6):1511-1518. doi: 10.1111/jam.13304. Epub 2016 Nov 3. PMID: 27681346 8:The steroid hormone 20-hydroxyecdysone promotes switching from autophagy to apoptosis by increasing intracellular calcium levels. Li YB, Li XR, Yang T, Wang JX, Zhao XF.Insect Biochem Mol Biol. 2016 Dec;79:73-86. doi: 10.1016/j.ibmb.2016.10.004. Epub 2016 Oct 21. PMID: 27777042 9:Identification of LmUAP1 as a 20-hydroxyecdysone response gene in the chitin biosynthesis pathway from the migratory locust, Locusta migratoria. Liu XJ, Sun YW, Li DQ, Li S, Ma EB, Zhang JZ.Insect Sci. 2016 Oct 3. doi: 10.1111/1744-7917.12406. [Epub ahead of print] PMID: 27696733 10:The Steroid Hormone 20-Hydroxyecdysone Promotes the Cytoplasmic Localization of Yorkie to Suppress Cell Proliferation and Induce Apoptosis. Wang D, Li XR, Dong DJ, Huang H, Wang JX, Zhao XF.J Biol Chem. 2016 Oct 7;291(41):21761-21770. Epub 2016 Aug 22. PMID: 27551043