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Merck
CN

E9004

α-Ecdysone

≥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

Key Documents

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Product Name

α-Ecdysone, ≥90%

InChI key

UPEZCKBFRMILAV-JMZLNJERSA-N

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

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

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

Quality Level

200

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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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9691
BCBW4130
BCCK7684
BCCC8948
BCBV6339

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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
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
Naoki Yamanaka et al.
Annual review of entomology, 58, 497-516 (2012-10-18)
The steroid hormone ecdysone is the central regulator of insect developmental transitions. Recent new advances in our understanding of ecdysone action have relied heavily on the application of Drosophila melanogaster molecular genetic tools to study insect metamorphosis. In this review
Laura Boulan et al.
Current biology : CB, 23(6), 473-478 (2013-03-13)
During the development of multicellular organisms, body growth is controlled at the scale of the organism by the activity of long-range signaling molecules, mostly hormones. These systemic factors coordinate growth between developing tissues and act as relays to adjust body
Jean-Philippe Parvy et al.
Development (Cambridge, England), 141(20), 3955-3965 (2014-09-26)
In most animals, steroid hormones are crucial regulators of physiology and developmental life transitions. Steroid synthesis depends on extrinsic parameters and autoregulatory processes to fine-tune the dynamics of hormone production. In Drosophila, transient increases of the steroid prohormone ecdysone, produced
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