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(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on

Ecdysone Struktur
3604-87-3
CAS-Nr.
3604-87-3
Bezeichnung:
(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on
Englisch Name:
Ecdysone
Synonyma:
ECDYSONE;A-ECDYSONE;Ecdyterone;α-Ecdysone;ALPHA-ECDYSON;ALPHA-ECYSONE;ALPHA-ECDYSONE;ECDYSONE, ALPHA-;ALPHA-ECDYSTERONE;α-Ecdysone ( >90%)
CBNumber:
CB8113524
Summenformel:
C27H44O6
Molgewicht:
464.63
MOL-Datei:
3604-87-3.mol

(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on Eigenschaften

Schmelzpunkt:
242°C
alpha 
20578 +62°
Siedepunkt:
488.1°C (rough estimate)
Dichte
1.0493 (rough estimate)
Brechungsindex
1.4482 (estimate)
storage temp. 
2-8°C
L?slichkeit
Methanol (Very Slightly, Heated)
pka
14.07±0.70(Predicted)
Aggregatzustand
Solid
Farbe
White to Off-White
Optische Aktivit?t
+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 Datenbank
3604-87-3(CAS DataBase Reference)

Sicherheit

S-S?tze: 22-24/25
WGK Germany  3
RTECS-Nr. FZ8170000
10

(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on Chemische Eigenschaften,Einsatz,Produktion Methoden

S-S?tze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.

Beschreibung

?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.

Verwenden

α-Ecdysone is a steroidal prohormone.

Stoffwechselwegen

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.

l?uterung methode

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.]

(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 169)Lieferanten
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3604-87-3((2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on)Verwandte Suche:


  • 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-
  • ALPHA-ECDYSON
  • ALPHA-ECDYSONE
  • ALPHA-ECDYSTERONE
  • 7,(5-ALPHA)-CHOLESTEN-2-BETA, 3-BETA, 14-ALPHA, 22R, 25-PENTOL-6-ONE
  • 2BETA,3BETA,14ALPHA,22[R],25-PENTAHYDROXY-7-CHOLESTEN-6-ONE
  • (2beta,3beta,5beta,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one
  • Ecdysterone(CyanotisArachnoiseaPe)60%ByHplc
  • 2β,3β,14α,22(r),25-pentahydroxy-7-cholesten-6-one
  • ALPHA-ECYSONE
  • β-Ecdysone[20-Hydroxyecdysone]
  • -ECDYSONE 98.0% BY HPLC
  • A-ECDYSONE
  • (2b,3b,5b,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one
  • (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(1S,2R)-2,5-dihydroxy-1,5-dimethyl-hexyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
  • (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methyl-heptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
  • (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
  • Gynostemma Gypenosides
  • (2S,3R,5R,9R,10R,13R,14S,17R)-17-((2S,3R)-3,6-dihydroxy-6-Methylheptan-2-yl)-2,3,14-trihydroxy-10,13-diMethyl-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one
  • Ecdyterone
  • 7, (5a)-CHOLESTEN-2, 3, 14a, 22R, 25-PENTOL-6-ONE
  • α-Ecdysone ( >90%)
  • Ecdysone USP/EP/BP
  • α-Ecdysone
  • Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2β,3β,5β,22R)-
  • Ecdysone 60% HPLC (90%)UV
  • Cholest-7-en-6-one,2,3,14,22,25-pentahydroxy-, (2b,3b,5b,22R)-
  • 7, (5β)-CHOLESTEN-2β, 3β, 14α, 22R, 25-PENTOL-6-ONE
  • 3604-87-3
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