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Merck
CN

44656

α-Ecdysone

≥99.0% (UV)

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
EC Number:
222-760-4
UNSPSC Code:
12352200
PubChem Substance ID:
329756531
Beilstein/REAXYS Number:
2422986
MDL number:
MFCD00042683

Key Documents

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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

assay

≥99.0% (UV)

application(s)

agriculture
environmental

storage temp.

−20°C

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General description

Prothoracic hormone (causes moulting in insects)

Other Notes

Prothorakal gland hormone

Regulatory Information

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E.D. Morgan et al.
Comp. Biochem. Biophys., 578, 99-99 (1977)
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
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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