|
| | Hydroxyecdysone Basic information |
| Product Name: | Hydroxyecdysone | | Synonyms: | BETA-ECDYSONE;BETA-ECDYSONE,2,3,14,20,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE;BETA-ECDYSTERONE;7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE;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 | | CAS: | 5289-74-7 | | MF: | C27H44O7 | | MW: | 480.64 | | EINECS: | 811-097-1 | | Product Categories: | Miscellaneous Natural Products;Steroids;Natural Plant Extract;sy;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors | | Mol File: | 5289-74-7.mol |  |
| | Hydroxyecdysone Chemical Properties |
| 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 | | InChI | InChI=1/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/s3 | | 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) |
| | Hydroxyecdysone Usage And Synthesis |
| 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 | | 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.] |
| | Hydroxyecdysone Preparation Products And Raw materials |
|
