An ecdysteroid hormone
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20-hydroxy Ecdysone

Item No. 16145

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-2β,3β,14,20,22R,25-hexahydroxy-cholest-7-en-6-one
CAS Number
5289-74-7
Synonyms
  • Ecdysterone
  • Isoinokosterone
Molecular Formula
C27H44O7
Formula Weight
480.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
243 nm
SMILES
O=C1[C@]2([H])C[C@@H](O)[C@@H](O)C[C@]2(C)[C@]3([H])C([C@@](CC[C@]4([H])[C@]([C@H](O)CCC(C)(O)C)(O)C)(O)[C@]4(C)CC3)=C1
InChi Code
InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
InChi Key
NKDFYOWSKOHCCO-YPVLXUMRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $54

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    10 mg

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    25 mg

    $158

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    50 mg

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    Product Description

    20-hydroxy Ecdysone is an ecdysteroid hormone produced in arthropod species that induces developmental changes associated with ecdysis and the completion of metamorphosis.1 It is also produced in plants as a defensive strategy to disrupt the development of insect pests.2 In target tissues, 20-hydroxy ecdysone binds to the nuclear hormone receptor, ecdysone receptor, initiating a signaling cascade that results in cell cycle arrest.1,3 Ecdysteroids such as this compound have been employed as tools in inducible gene regulation systems controlled by reporter cells transfected with the ecdysone receptor.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fallon, A.M., and Gerenday, A. Ecdysone and the cell cycle: Investigations in a mosquito cell line. J. Insect Physiol. 56(10), 1396-1401 (2010).

    2. Boo, K.H., Lee, D., Jeon, G.L., et al. Distribution and biosynthesis of 20-hydroxyecdysone in plants of Achyranthes japonica Nakai. Biosci. Biotechnol. Biochem. 74(11), 2226-2231 (2010).

    3. Cai, M.J., Dong, D.J., Wang, Y., et al. G-protein-coupled receptor participates in 20-hydroxyecdysone signaling on the plasma membrane. Cell Commun. Signal. 12, 11-16 (2014).

    4. Saez, E., Nelson, M.C., Eshelman, B., et al. Identification of ligands and coligands for the ecdysone-regulated gene switch. Proc. Natl. Acad. Sci. USA 97(26), 14512-14517 (2000).

    5. Karzenowski, D., Potter, D.W., and Padidam, M. Inducible control of transgene expression with ecdysone receptor: Gene switches with high sensitivity, robust expression, and reduced size. Biotechniques 39(2), 191-192 (2005).