Hydroxyecdysone
Synonym(s):β-Ecdysone;2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one;Ecdysterone;Insect moulting hormone;Polypodine A
- CAS NO.:5289-74-7
- Empirical Formula: C27H44O7
- Molecular Weight: 480.64
- MDL number: MFCD00036740
- EINECS: 811-097-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 08:26:49
What is Hydroxyecdysone?
Chemical properties
White or off-white powder, odorless, hygroscopic, the color gradually becomes darker when exposed to light. Soluble in ethanol, slightly soluble in acetone, slightly soluble in hot water, ethyl acetate, chloroform, almost insoluble in ether, derived from Leulu, Achyranthes bidentata, Cyanotis, arachnoidea, Pfaffia glomerata.
The Uses of Hydroxyecdysone
20-Hydroxyecdysone has been used:
- in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sexta
- in Schneider′s medium to reproduce ex-vivo imaginal disc eversion
- as a supplement in Mcl8 medium for culturing Drosophila wing imaginal discs
What are the applications of Application
20-Hydroxyecdysone is a ecdysteroid in both plant and animal species that controls cell death
Definition
ChEBI: 20-hydroxyecdysone is an ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. It has a role as a plant metabolite and an animal metabolite. It is a 20-hydroxy steroid, an ecdysteroid, a 14alpha-hydroxy steroid, a 3beta-sterol, a 2beta-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid and a phytoecdysteroid. It is functionally related to an ecdysone.
Biochem/physiol Actions
20-Hydroxyecdysone is an ecdysteroid hormone that plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in molting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).
storage
+4°C
Purification Methods
Crystallise -ecdyson from water, tetrahydrofuran/pet ether, MeOH and EtOAc after chromatographic purification. It has max (EtOH) at 240nm ( 12,670 M-1cm-1). [Also IR & NMR: Hüppi & Siddall J Am Chem Soc 89 6799 1967, Kametani et al. Tetrahedron Lett 21 4855 1980, Beilstein 8 IV 343.]
Properties of Hydroxyecdysone
Melting point: | 242-244 °C |
Boiling point: | 498.63°C (rough estimate) |
Density | 1.0760 (rough estimate) |
refractive index | 1.5800 (estimate) |
storage temp. | Sealed in dry,Store in freezer, under -20°C |
solubility | alcohol: soluble |
form | powder |
pka | 14.13±0.70(Predicted) |
color | white |
Merck | 13,3525 |
BRN | 1917578 |
CAS DataBase Reference | 5289-74-7(CAS DataBase Reference) |
Safety information for Hydroxyecdysone
Signal word | Warning |
Pictogram(s) |
Environment GHS09 |
GHS Hazard Statements |
H410:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. P391:Collect spillage. Hazardous to the aquatic environment |
Computed Descriptors for Hydroxyecdysone
InChIKey | NKDFYOWSKOHCCO-YPVLXUMRSA-N |
SMILES | O[C@@]12CC[C@]([H])([C@](O)(C)[C@H](O)CCC(O)(C)C)[C@]1(CC[C@]1([H])[C@]3(C[C@H](O)[C@H](O)C[C@@]3([H])C(=O)C=C21)C)C |&1:1,4,6,9,17,20,22,24,26,29,r| |
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