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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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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
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
Florentina Rus et al.
The EMBO journal, 32(11), 1626-1638 (2013-05-09)
Throughout the animal kingdom, steroid hormones have been implicated in the defense against microbial infection, but how these systemic signals control immunity is unclear. Here, we show that the steroid hormone ecdysone controls the expression of the pattern recognition receptor
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
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