3604-87-3

Basic information

• Product Name: Ecdysone
• Synonyms: 2,3,14,22,25-pentahydroxy-,(2-beta,3-beta,5-beta,22r)-cholest-7-en-6-on;2-beta,3-beta,14,22,25-pentahydroxy-,(20s,22r)-5-beta-cholest-7-en-6-on;ECDYSONE;ECDYSONE, ALPHA-;2BETA,3BETA,14ALPHA,22[R],25-PENTAHYDROXY-7-CHOLESTEN-6-ONE;ALPHA-ECDYSON;ALPHA-ECDYSONE;ALPHA-ECDYSTERONE
• CAS NO: 3604-87-3
• Molecular Formula: C27H44O6
• Molecular Weight: 464.63
• EINECS: 222-760-4
• Product Categories: Steroids;Natural Plant Extract
• Mol File: 3604-87-3.mol

Chemical Properties

• Melting Point: 242°C
• Boiling Point: 488.1°C (rough estimate)
• Flash Point: 350 °C
• Appearance: powder
• Density: 1.0493 (rough estimate)
• Vapor Pressure: 1.26E-18mmHg at 25°C
• Refractive Index: 1.4482 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Very Slightly, Heated)
• PKA: 14.07±0.70(Predicted)
• Merck: 13,3525
• BRN: 2422986
• CAS DataBase Reference: Ecdysone(CAS DataBase Reference)
• NIST Chemistry Reference: Ecdysone(3604-87-3)
• EPA Substance Registry System: Ecdysone(3604-87-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: FZ8170000
• F: 10
• Hazardous Substances Data: 3604-87-3(Hazardous Substances Data)

Usage

Uses

α-Ecdysone is a steroidal prohormone.

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.

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.]

InChI:InChI=1/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17?,19-,20+,22+,23-,25+,26+,27+/m0/s1

Upstream product

• 19327-83-4 Acetic acid (2S,3R,5S,9R,10R,13R,14S,17R)-3-acetoxy-14-hydroxy-10,13-dimethyl-6-oxo-17-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 
• 41408-38-2 2,22-dideoxyecdysone 
• 52717-49-4 26-hydroxyecdysone 
• 77273-84-8 3-((2R,3S,4aR,4bR,6aR,6bR,7S,8R,9aS,10aS,12aS)-2,3-Diacetoxy-10a-hydroxy-4a,6a,7-trimethyl-12-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester 
• 82183-62-8 ecdysone-22-phosphate 
• 19466-43-4 (20S,22R)-2β,3β,22-triacetoxy-14α,25-dihydroxy-5β-cholest-7-en-6-one 
• 77260-37-8 Acetic acid (2S,3R,5S,9R,10R,13R,14S,17R)-3-acetoxy-14-hydroperoxy-10,13-dimethyl-6-oxo-17-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 
• 77260-32-3 3-((2R,3S,4aR,4bS,6aS,6bR,7S,8R,9aS,10aS,10bR,11S,12aS)-2,3-Diacetoxy-11-bromo-4a,6a,7-trimethyl-12-oxo-octadecahydro-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester 
• 77260-34-5 3-((2R,3S,4aR,4bR,6aR,6bR,7S,8R,9aS,12aS)-2,3-Diacetoxy-4a,6a,7-trimethyl-12-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,12,12a-tetradecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester 
• 77260-33-4 3-((2R,3S,4aR,4bR,6aS,6bR,7S,8R,9aS,10aR,12aS)-2,3-Diacetoxy-4a,6a,7-trimethyl-12-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester 
• 77260-31-2 3-((2R,3S,4aR,4bS,6aS,6bR,7S,8R,9aS,10aS,10bR,12aS)-2,3-Diacetoxy-4a,6a,7-trimethyl-12-oxo-octadecahydro-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester 
• 77260-36-7 Acetic acid (2S,3R,5S,9R,10R,13R,17R)-3-acetoxy-10,13-dimethyl-6-oxo-17-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 

Downstream Products

• 5289-74-7 20-Hydroxyecdysone 
• 75319-59-4 3-epi-26-hydroxyecdysone 
• 52717-49-4 26-hydroxyecdysone 
• 5289-74-7 Coronatasterone 
• 71939-17-8 3-epi-20,26-dihydroxyecdysone 
• 19458-46-9 20,26-dihydroxyecdysone 
• 39750-00-0 3-Dehydroecdyson 

Relevant articles and documents

STEREOSPECIFIC CONVERSION OF DIOSGENIN TO LABELED a-ECDYSONE

15,16-3H2>-α-Ecdysone has been synthesized from diosgenin.

PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. VI. α-ECDYSONE 22-SULFATE - A NEW ECDYSTEROID FROM Silene brahuica

A phytoecdysteroid consisting of the sodium salt of α-ecdysone 22-sulfate has been isolated from the roots of Silene brahuica Boiss.

STUDY ON THE BIOSYNTHESIS OF ECDYSONE PART IV: Synthesis of high specific activity -2,22-dideoxyecdysone Tissue distribution of the C-22 hydroxylase in Locusta migratoria

We have synthesized a tritiated form of 2,22-dideoxyecdysone -3β,14α,25-trihydroxy-5β-cholest-7-en-6-one> of high specific activity (2.2 TBq/mmol).We have examined the capacity of various endocrine (prothoracic glands, follicle cells) and peripheral (fat body, Malpighian tubules) tissues of Locusta migratoria to use this molecule as a precursor of ecdysone biosynthesis.Efficient conversion of 2,22-dideoxyecdysone to 2-deoxyecdysone and to ecdysone could principally be monitored in the prothoracic glands and follicle cells.

Identification of Ecdysone-22-phosphate and 2-Deoxyecdysone-22-phosphate in Eggs of the Desert Locust, Schistocerca gregaria, by Fast Atom Bombardment Mass Spectrometry and N.M.R. Spectroscopy

Ecdysone-22-phosphate and 2-deoxyecdysone-22-phosphate have been purified by h.p.l.c. from eggs of the desert locust, Schistocerca gregaria, and their structures determined primarily by Fast Atom Bombardment mass spectrometry and 1H, 13C, and 31P n.m.r.spectroscopy.

THE CONSTITUENTS OF PARIS VERTICILLATA M.V. BIEB.

Nine compounds (1-9) have been isolated from the whole plants of Paris verticillata M.v.BIEB. (Liliaceae) and their structures characterized.They can be divided into four groups; phytosteryl derivatives (I, phytosteryl (6'-palmitoyl)-β-D-glucopyranoside; 2, the despalmitate of 1), phytoecdysones (3, ecdysone; 4, ajugasterone A; 5, ecdysterone), pennogenin glycosides (6, pennogenin tetraglycoside (T-g); 7, prototype glycoside of 6), and kaempferol glycosides (8, kaempferol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside; 9, 7-O-β-D-glucopyranosyl kaempferol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside).Keywords: Paris verticillata; Liliaceae; phytosteryl (6'-palmitoyl)-glucoside; ecdysone; ajugasterone A; ecdysterone; pennogenin glycoside; furostanol glycoside; kaempferol glycoside