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H5142

20-Hydroxyecdysone

Name: 20-Hydroxyecdysone
Brand: SIGMA

≥93% (HPLC), ecdysteroid hormone, powder

Synonym(s):

β-Ecdysone, 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one, Ecdysterone, Insect moulting hormone, Polypodine A

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₄O₇

CAS Number:

5289-74-7

Molecular Weight:

480.63

NACRES:

NA.77

PubChem Substance ID:

24895674

UNSPSC Code:

12352200

MDL number:

MFCD00036740

Beilstein/REAXYS Number:

1917578

Assay:

≥93% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

20-Hydroxyecdysone, ≥93% (HPLC), powder

sterility

non-sterile

Quality Level

100

assay

≥93% (HPLC)

form

powder

color

white to off-white

solubility

alcohol: soluble

application(s)

agriculture
environmental

shipped in

ambient

storage temp.

−20°C

SMILES string

[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3(O)C1=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]24C)[C@@](C)(O)[C@H](O)CCC(C)(C)O

InChI

1S/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+/m0/s1

InChI key

NKDFYOWSKOHCCO-YPVLXUMRSA-N

Description

Application

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

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 Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Towards long term cultivation of Drosophila wing imaginal discs in vitro

Handke B, et al.

PLoS ONE, 9(9), e107333-e107333 (2014)

Broad-complex functions in postembryonic development of the cockroach Blattella germanica shed new light on the evolution of insect metamorphosis.

Jia-Hsin Huang et al.

Biochimica et biophysica acta, 1830(1), 2178-2187 (2012-10-09)

Insect metamorphosis proceeds in two modes: hemimetaboly, gradual change along the life cycle; and holometaboly, abrupt change from larvae to adult mediated by a pupal stage. Both are regulated by 20-hydroxyecdysone (20E), which promotes molts, and juvenile hormone (JH), which

Reciprocal interactions between olfactory receptor axons and olfactory nerve glia cultured from the developing moth Manduca sexta

Tucker ES and Tolbert LP

Developmental Biology, 260(1), 9-30 (2003)

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