20-Hydroxyecdysone
Grundinformationen
- CAS
5289-74-7- Standard-SMILES
CC(C)(O)CC[C@@H](O)[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
NKDFYOWSKOHCCO-YPVLXUMRSA-N- Summenformel
- C27H44O7
- Durchschnittliche Molmasse
- 480,6 g/mol
- Monoisotopische Masse
- 480,30870375
Überblick
20-hydroxyecdysone is an ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. It has a role as an animal metabolite and a plant metabolite. It is an ecdysteroid, a phytoecdysteroid, a 3beta-sterol, a 20-hydroxy steroid, a 2beta-hydroxy steroid, a 14alpha-hydroxy steroid, a 22-hydroxy steroid and a 25-hydroxy steroid. It is functionally related to an ecdysone.
Namen und Bezeichner
- Bevorzugter Name
- 20-Hydroxyecdysone
- IUPAC
- (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
- Englischer Name
- Hydroxyecdysone
- Summenformel
- C27H44O7
- Molmasse
- 480.64
Namen und Synonyme
20-HYDROXYECDYSONE5289-74-7Crustecdysonebeta-EcdysoneIsoinokosteroneCommisteroneCrustecdysonEcdysteronViticosteroneTHE-7Ekdistenbeta-ECDYSTERONE
Weitere Namen anzeigen
ECDYSTERONEβ-Ecdysteroneβ-EcdysoneB-ECDYSONEEcdysteroid
20-OH ecdysoneEcdystenBIO101779A7KPL0YBIO-101NSC-629484Bio 101DTXSID5040388
Datenbank-Bezeichner
- CAS
5289-74-7- PubChem CID
- 5459840
- DTXSID
DTXSID5040388- ChEMBL
CHEMBL224128- ChEBI
CHEBI:16587- UNII
- 779A7KPL0Y
- EC Number
- 811-097-1
- Nikkaji
- J13.425B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 138 Ų
- H-Brücken-Donoren
- 6
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 34
- Formalladung
- 0
- Komplexität
- 869
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Melting Point237.5 - 239.5 °C
Physical DescriptionSolid
Collision Cross Section
221.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
217.64 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 242 · 242-244 °C
- Siedepunkt
- 498.63 °C · 498.63°C (rough estimate)
- Dichte
- 1.076 · 1.0760 (rough estimate)
- Brechungsindex
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- alcohol: soluble
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 3.1% (1 of 32) of reports.
Warning
H400 (90.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 32 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAquatic Acute 1 (90.6%)
Sicherheitsdaten
- F
- 10
- wgk
- 2
- hs_code
- 29372900
- RTECS-Nr.
- FZ8060000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Sarconeos activates MAS receptors in muscle cells involved in the Renin-Angiotensin System which results in activation of the P13K/AKT/mTOR pathway. This activation increases protein production and helps preserve muscle mass and strength. In addition, Sarconeos also stimulates the AMPK/ACC pathway, which increases energy production and supports muscle strength and mobility.
Cellular LocationsExtracellular
Anwendungen
Beschreibung20-Hydroxyecdysone (also known as Ecdysterone) is a hormone-like substance widely found in animals and plants, with a steroid ring at the core of its structure. It has the function of promoting arthropod molting and protecting plants from insects. Studies have shown that when used as a supplement, ecdysterone has a positive effect on human measurements and performance parameters, and is included in the World Anti-Doping Agency's banned list, but it has recently been found that there is a lack of scientific evidence to support WADA's ban on this substance.
Verwenden20-Hydroxyecdysone has been used:in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sextain Schneider′s medium to reproduce ex-vivo imaginal disc eversionas a supplement in Mcl8 medium for culturing Drosophila wing imaginal discsas an insect molting hormone
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