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E9004

Sigma-Aldrich

α-Ecdysone

≥90%

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
Beilstein:
2422986
EC Number:
222-760-4
MDL number:
MFCD00042683
UNSPSC Code:
51111800
PubChem Substance ID:
24894686
NACRES:
NA.77

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

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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 Code

11 - Combustible Solids

WGK

WGK 3

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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W Robert Shaw et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(16), 5854-5859 (2014-04-09)
Anopheles gambiae mosquitoes are major African vectors of malaria, a disease that kills more than 600,000 people every year. Given the spread of insecticide resistance in natural mosquito populations, alternative vector control strategies aimed at reducing the reproductive success of
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
Juri Hikiba et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 915-916, 52-56 (2013-01-22)
The concentration changes of endogenous ecdysteroids are closely related to the regulation of insect growth and development. Although they are frequently measured by immunoassays with anti-steroid antibodies, the separate estimations of the individual concentrations of ecdysone and other ecdysteroids with
Cecilia Stahl Vieira et al.
Developmental and comparative immunology, 114, 103864-103864 (2020-09-13)
Rhodnius prolixus is an insect vector of two flagellate parasites, Trypanosoma rangeli and Trypanosoma cruzi, the latter being the causative agent of Chagas disease in Latin America. The R. prolixus neuroendocrine system regulates the synthesis of the steroid hormone ecdysone
Hiroyuki Shirai et al.
PloS one, 7(11), e49348-e49348 (2012-11-21)
Three distinct classes of nuclear receptors, EcR, E75, and HR3, are key regulators in the ecdysone-inducible gene activation cascade in insects. The transcription of these genes is induced by ecdysone (20E) differently, although the detailed mechanisms underlying their responses to
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