Ecdysone Chemical Properties

Melting point:

242°C

alpha 

20578 +62°

Boiling point:

488.1°C (rough estimate)

Density 

1.0493 (rough estimate)

refractive index 

1.4482 (estimate)

storage temp. 

2-8°C

solubility 

Methanol (Very Slightly, Heated)

pka

14.07±0.70(Predicted)

form 

Solid

color 

White to Off-White

optical activity

+5820 (c 0.1, ethanol)

Merck 

13,3525

BRN 

2422986

InChIKey

UPEZCKBFRMILAV-JMZLNJERSA-N

SMILES

[C@H]1(C[C@@]2([C@](C)(C[C@@H]1O)[C@]1([H])C([C@]3([C@@](CC1)(C)[C@@H]([C@H](C)[C@@H](CCC(C)(C)O)O)CC3)O)=CC2=O)[H])O

LogP

0.870 (est)

CAS DataBase Reference

3604-87-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

FZ8170000

F 

10

MSDS

• Language:English Provider:SigmaAldrich

Ecdysone Usage And Synthesis

Description

?Ecdysterone, also known as ecdysone or β-ecdysone, is a hormone that regulates the growth and development of insects. In 1954, Butenandt et al. isolated 250mg of the initial insect metamorphic active substance, ecdysone, from 500kg of silkworm pupae. Since then, various similar substances have been isolated from many plants. It has been found that ecdysteroids are not only more abundant in the plant kingdom compared to the animal kingdom, but also widely distributed and abundant in resources. Examples of ferns that contain ecdysteroids include Chinese cornbind, Sichuan cornbind, mulberry leaves, Dectenium heterocarpon, water plantain, Ginkgo biloba, yew, Thelypteris palustris, and Cyrtomium falcatum, among others.

Uses

α-Ecdysone is a steroidal prohormone.

Definition

ChEBI: Ecdysone is a 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone. It has a role as a prohormone. It is a 2beta-hydroxy steroid, a 14alpha-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid, a 6-oxo steroid, a 3beta-sterol and an ecdysteroid. It derives from a hydride of a 5beta-cholestane.

target

Sodium Channel | ATPase | Potassium Channel | Autophagy

Metabolic pathway

When white mice are administered 3H-ecdyson, (2b,3b,14a,22(R),25-pentahydroxy-5b-cholest-7-ene-6- one) by injection intraperitoneally, ecdysone is metabolized via hydroxylation at C14, followed by reduction of ring B into the 6a-hydroxy derivative and epimerization at C3.

storage

+4°C

Purification Methods

Recrystallise -ecdyson from tetrahydrofuran/pet ether and from H2O as a hydrate. It has been purified by chromatogaphy on Al2O3 and elution with EtOAc/MeOH. It has max at 242nm ( 12,400). Its acetate has m 214-216o from EtOAc/pet ether, and the 2,4-dinitrophenylhydrazone has m 170-175o(dec) from EtOAc. [Karlson & Hoffmeister Justus Liebigs Ann Chem 662 1 1963, Karlson Pure Appl Chem 14 75 1967, Beilstein 8 IV 3613.]

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