(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on
alpha-Ecdysone
Grundinformationen
- CAS
3604-87-3- Standard-SMILES
C[C@@H]([C@H](O)CCC(C)(C)O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C- InChIKey
UPEZCKBFRMILAV-HXUSGADLSA-N- Summenformel
- C27H44O6
- Durchschnittliche Molmasse
- 464,6 g/mol
- Monoisotopische Masse
- 464,31378912
Überblick
(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2R,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 has been reported in Manduca sexta and Cranfillia vulcanica with data available.
Namen und Bezeichner
- Bevorzugter Name
- alpha-Ecdysone
- IUPAC
- (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2R,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
- Lokaler Name
- (2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on
- Englischer Name
- Ecdysone
- Summenformel
- C27H44O6
- Molmasse
- 464.63
Namen und Synonyme
alpha-EcdysoneDTXSID2020553(20R,22R)-2beta,3beta,14,22,25-Pentahydroxy-5beta-cholest-7-en-6-oneα-EcdysoneECDYSONEA-ECDYSONEEcdyteroneALPHA-ECDYSONALPHA-ECYSONEECDYSONE, ALPHA-ALPHA-ECDYSTERONEEcdysone USP/EP/BP
Datenbank-Bezeichner
- CAS
3604-87-3- PubChem CID
- 165339208
- DTXSID
DTXSID2020553
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 118 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 821
Physikochemische Eigenschaften
- Schmelzpunkt
- 242 °C · 242°C
- Siedepunkt
- 488.1 °C · 488.1°C (rough estimate)
- Dichte
- 1.0493 · 1.0493 (rough estimate)
- Brechungsindex
- 1.4482 · 1.4482 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Methanol (Very Slightly, Heated)
- pka
- 14.07 · 14.07±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Merck
- 13 · 13,3525
- BRN
- 2422986 · 2422986
- Major Application
- agricultureenvironmental
- 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
- 0.87 · 0.870 (est)
- CAS Datenbank
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 10
- wgk
- 3
- RTECS-Nr.
- FZ8170000
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungEcdysterone, 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.
Verwendenα-Ecdysone is a steroidal prohormone.
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