Hydroxyecdysone Chemical Properties

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

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+/s3

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|

LogP

-0.270 (est)

CAS DataBase Reference

5289-74-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

2

RTECS 

FZ8060000

F 

10

HS Code 

29372900

MSDS

• Language:English Provider:20-Hydroxyecdysone
• Language:English Provider:SigmaAldrich

Hydroxyecdysone Usage And Synthesis

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.

Uses

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
as an insect molting hormone

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.]

Hydroxyecdysone(5289-74-7)Related Product Information

• β-Ecdysone[20-Hydroxyecdysone]
• 4'-Hydroxyacetophenone
• Dehydroepiandrosterone
• 2'-Hydroxyacetophenone
• 1-Decen-3-ol
• 3,7-DIMETHYL-1-OCTEN-3-OL
• 4-Methyl-3-decen-5-ol
• 2-Methyl-3-buten-2-ol
• turkesterone
• 1-N-PROPYLCYCLOPENTANOL
• 5-METHYL-2-HEPTEN-4-ONE
• 2-METHYL-1-PENTEN-3-OL
• TRANS-2-METHYLCYCLOPENTANOL
• (S)-1,2-DECANEDIOL
• 4-METHYL-4-HEPTEN-3-OL
• (S)-1,2-OCTANEDIOL
• Ponesterone A
• Hydroxyecdysone
• Ecdysterone