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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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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

Related Categories

Bioactive Small Molecules

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)

Regulatory Information

涉药品监管产品

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Ecdysone receptors: from the Ashburner model to structural biology.

Ronald J Hill et al.

Annual review of entomology, 58, 251-271 (2012-10-18)

In 1974, Ashburner and colleagues postulated a model to explain the control of the puffing sequence on Drosophila polytene chromosomes initiated by the molting hormone 20-hydroxyecdysone. This model inspired a generation of molecular biologists to clone and characterize elements of

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

Towards long term cultivation of Drosophila wing imaginal discs in vitro

Handke B, et al.

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

Transcriptome Analysis of

Danielle Christesen et al.

G3 (Bethesda, Md.), 7(2), 467-479 (2016-12-16)

Importance of miRNA stability and alternative primary miRNA isoforms in gene regulation during Drosophila development.

Li Zhou et al.

eLife, 7 (2018-07-20)

Mature microRNAs (miRNAs) are processed from primary transcripts (pri-miRNAs), and their expression is controlled at transcriptional and post-transcriptional levels. However, how regulation at multiple levels achieves precise control remains elusive. Using published and new datasets, we profile a time course

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Global Trade Item Number

SKU	GTIN
H5142-10MG	04061833797396
H5142-5MG	04061833797419
H5142-25MG	04061832850443

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