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E9004

α-Ecdysone

Name: &#945;-Ecdysone
Brand: SIGMA

≥90%, Insect molting hormone, powder

Synonym(s):

2β,3β,14α,22(R),25-Pentahydroxy-7-cholesten-6-one

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₄O₆

CAS Number:

3604-87-3

Molecular Weight:

464.63

NACRES:

NA.77

PubChem Substance ID:

24894686

UNSPSC Code:

51111800

EC Number:

222-760-4

MDL number:

MFCD00042683

Beilstein/REAXYS Number:

2422986

Assay:

≥90%

Form:

powder

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Properties

Product Name

α-Ecdysone, ≥90%

sterility

non-sterile

assay

≥90%

form

powder

solubility

methanol: 20 mg/mL, clear, colorless to faintly yellow

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@H](C)[C@H](O)CCC(C)(C)O

InChI

1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1

InChI key

UPEZCKBFRMILAV-JMZLNJERSA-N

Description

General description

α-Ecdysone is a phytoecdysteroid, synthesized from cholesterol, and one of the major insect molting hormones. Ecdysone is secreted by the ecdysial glands present in insects.

Application

α-Ecdysone has been used:

to study its effects on Drosophila melanogaster′s sexual maturation
to study its effects on specification of neurons in Drosphila male-specific neurite
as a standard to evaluate the ecdysteroid levels by liquid chromatography-mass spectrometry (LC-MS/MS)

Biochem/physiol Actions

Ecdysone exerts its effects via the ecdysone receptor and regulates larval molting, reproduction, and metamorphosis in insects.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Hormonal regulation and developmental role of Krüppel homolog 1, a repressor of metamorphosis, in the silkworm Bombyx mori.

Takumi Kayukawa et al.

Developmental biology, 388(1), 48-56 (2014-02-11)

Juvenile hormone (JH) has an ability to repress the precocious metamorphosis of insects during their larval development. Krüppel homolog 1 (Kr-h1) is an early JH-inducible gene that mediates this action of JH; however, the fine hormonal regulation of Kr-h1 and

Developmental checkpoints and feedback circuits time insect maturation.

Kim F Rewitz et al.

Current topics in developmental biology, 103, 1-33 (2013-01-26)

The transition from juvenile to adult is a fundamental process that allows animals to allocate resource toward reproduction after completing a certain amount of growth. In insects, growth to a species-specific target size induces pulses of the steroid hormone ecdysone

Hormone-responsive enhancer-activity maps reveal predictive motifs, indirect repression, and targeting of closed chromatin.

Daria Shlyueva et al.

Molecular cell, 54(1), 180-192 (2014-04-02)

Steroid hormones act as important developmental switches, and their nuclear receptors regulate many genes. However, few hormone-dependent enhancers have been characterized, and important aspects of their sequence architecture, cell-type-specific activating and repressing functions, or the regulatory roles of their chromatin

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