| Identification | More | [Name]
Hydroxyecdysone | [CAS]
5289-74-7 | [Synonyms]
20-HYDROXYECDYSON
20-HYDROXYECDYSONE
2B,3B,14A,20,22[R],25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
2b,3b,14a,20b,22,25-hexahydroxycholest-7-en-6-one
2BETA,3BETA,14ALPHA,20BETA,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-TRIHYDROXY-10,13-DIMETHYL-17-((1R,2R)-1,2,5-TRIHYDROXY-1,5-DIMETHYL-HEXYL)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-6-ONE
7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE
B-ECDYSONE
BETA-ECDYSON
BETA-ECDYSONE
BETA-ECDYSONE,2,3,14,20,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
BETA-ECDYSTERONE
ECDYSONE, BETA-
ECDYSTERONE
hydroxyecdysone
HYDROXYECDYSONE, 20-
INSECT MOULTING HORMONE
POLYPODINE A
2,3,14,20,22,25-hexahydroxy-,(2-beta,3-beta,5-beta,22r)-cholest-7-en-6-on
2-beta,3-beta,14,20,22,25-hexahydroxy-5-beta-cholet-7-en-6-one | [EINECS(EC#)]
811-097-1 | [Molecular Formula]
C27H44O7 | [MDL Number]
MFCD00036740 | [Molecular Weight]
480.63 | [MOL File]
5289-74-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
242-244 °C
| [Boiling point ]
498.63°C (rough estimate) | [density ]
1.0760 (rough estimate) | [refractive index ]
1.5800 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
alcohol: soluble
| [form ]
powder
| [pka]
14.13±0.70(Predicted) | [color ]
white
| [Merck ]
13,3525 | [BRN ]
1917578 | [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| | [LogP]
-0.270 (est) | [CAS DataBase Reference]
5289-74-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
FZ8060000
| [F ]
10 | [HS Code ]
29372900 |
| Hazard Information | Back Directory | [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.
| [Uses]
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
as an insect molting hormone | [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, protect from light | [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.] |
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