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HomeProduct name listHydroxyecdysone

Hydroxyecdysone

Synonym(s):β-Ecdysone;2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one;Ecdysterone;Insect moulting hormone;Polypodine A

  • CAS NO.:5289-74-7
  • Empirical Formula: C27H44O7
  • Molecular Weight: 480.64
  • MDL number: MFCD00036740
  • EINECS: 811-097-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
Hydroxyecdysone Structural

What is Hydroxyecdysone?

Chemical properties

White or off-white powder, odorless, hygroscopic, the color gradually becomes darker when exposed to light. Soluble in ethanol, slightly soluble in acetone, slightly soluble in hot water, ethyl acetate, chloroform, almost insoluble in ether, derived from Leulu, Achyranthes bidentata, Cyanotis, arachnoidea, Pfaffia glomerata.

The Uses of Hydroxyecdysone

20-Hydroxyecdysone has been used:

  • in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sexta
  • in Schneider′s medium to reproduce ex-vivo imaginal disc eversion
  • as a supplement in Mcl8 medium for culturing Drosophila wing imaginal discs

What are the applications of Application

20-Hydroxyecdysone is a ecdysteroid in both plant and animal species that controls cell death

Definition

ChEBI: 20-hydroxyecdysone is an ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. It has a role as a plant metabolite and an animal metabolite. It is a 20-hydroxy steroid, an ecdysteroid, a 14alpha-hydroxy steroid, a 3beta-sterol, a 2beta-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid and a phytoecdysteroid. It is functionally related to an ecdysone.

Biochem/physiol Actions

20-Hydroxyecdysone is an ecdysteroid hormone that plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in molting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).

storage

+4°C

Purification Methods

Crystallise -ecdyson from water, tetrahydrofuran/pet ether, MeOH and EtOAc after chromatographic purification. It has max (EtOH) at 240nm ( 12,670 M-1cm-1). [Also IR & NMR: Hüppi & Siddall J Am Chem Soc 89 6799 1967, Kametani et al. Tetrahedron Lett 21 4855 1980, Beilstein 8 IV 343.]

Properties of Hydroxyecdysone

Melting point: 242-244 °C
Boiling point: 498.63°C (rough estimate)
Density  1.0760 (rough estimate)
refractive index  1.5800 (estimate)
storage temp.  Sealed in dry,Store in freezer, under -20°C
solubility  alcohol: soluble
form  powder
pka 14.13±0.70(Predicted)
color  white
Merck  13,3525
BRN  1917578
CAS DataBase Reference 5289-74-7(CAS DataBase Reference)

Safety information for Hydroxyecdysone

Signal word Warning
Pictogram(s)
ghs
Environment
GHS09
GHS Hazard Statements H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P273:Avoid release to the environment.
P391:Collect spillage. Hazardous to the aquatic environment

Computed Descriptors for Hydroxyecdysone

InChIKey NKDFYOWSKOHCCO-YPVLXUMRSA-N
SMILES O[C@@]12CC[C@]([H])([C@](O)(C)[C@H](O)CCC(O)(C)C)[C@]1(CC[C@]1([H])[C@]3(C[C@H](O)[C@H](O)C[C@@]3([H])C(=O)C=C21)C)C |&1:1,4,6,9,17,20,22,24,26,29,r|

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