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
• Article Data: 7

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 
• 19466-43-4 (20S,22R)-2β,3β,22-triacetoxy-14α,25-dihydroxy-5β-cholest-7-en-6-one 
• 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 
• 77260-37-8 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 
• 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 
• 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 
• 52717-49-4 26-hydroxyecdysone 
• 82183-62-8 ecdysone-22-phosphate 

Downstream Products

• 39750-00-0 3-Dehydroecdyson 
• 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 

Relevant articles and documents

STEREOSPECIFIC CONVERSION OF DIOSGENIN TO LABELED a-ECDYSONE

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

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.

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