20-Hydroxyecdysone

20-Hydroxyecdysone
Skeletal formula of 20-hydroxyecdysone
Ball-and-stick model of the 20-hydroxyecdysone molecule
Clinical data
Pregnancy
category
  • X
Routes of
administration		Oral
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
Elimination half-life4-9 hours
ExcretionUrinary:?%
Identifiers
  • (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.241.312 Edit this at Wikidata
Chemical and physical data
FormulaC27H44O7
Molar mass480.642 g·mol−1
3D model (JSmol)
  • O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
  • 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 checkY
  • Key:NKDFYOWSKOHCCO-YPVLXUMRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. It is also a phytoecdysteroid produced by various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides where its purpose is presumably to disrupt the development and reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In humans, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein-coding gene.[1]

  1. ^ Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, et al. (July 2019). "Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans". Archives of Toxicology. 93 (7): 1807–1816. doi:10.1007/s00204-019-02490-x. hdl:11573/1291269. PMID 31123801. S2CID 163166547.