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H5142

Sigma-Aldrich

20-Hydroxyecdysone

≥93% (HPLC), powder

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Synonym(s):
β-Ecdysone, 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one, Ecdysterone, Insect moulting hormone, Polypodine A
Empirical Formula (Hill Notation):
C27H44O7
CAS Number:
Molecular Weight:
480.63
Beilstein:
1917578
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

sterility

non-sterile

Quality Level

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

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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).

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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)
Balpreet Bhogal et al.
Development (Cambridge, England), 143(12), 2147-2159 (2016-06-04)
Dendritic arbor morphology is a key determinant of neuronal function. Once established, dendrite branching patterns must be maintained as the animal develops to ensure receptive field coverage. The translational repressors Nanos (Nos) and Pumilio (Pum) are required to maintain dendrite

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