20-Hydroxyecdysone

Specifications / Handling

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Product Details
Synonyms	β-Ecdysone; Ecdysterone; BRN 1917578 ; NSC 629484; Commisterone; Crustecdyson; Polypodine A; 2β,3β,14α,20R,22R,25-Hexahydroxy-5β-cholest-7-en-6-one
Product Type	Chemical
Properties
Formula	C₂₇H₄₄O₇
MW	480.6
Merck Index	14: 3491
CAS	5289-74-7
Source/Host Chemicals	Isolated from Ipomoea hederacea.
Purity Chemicals	≥95% (HPLC)
Appearance	White solid.
Solubility	Soluble in water, ethanol, methanol, DMSO or acetic acid.
Identity	Identity determined by ¹H-NMR.
InChi Key	NKDFYOWSKOHCCO-MQMWGCQISA-N
Smiles	[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)C3CC[C@]12C)[C@@](C)(O)[C@H](O)CCC(C)(C)O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

A member of the ecdysteroid family.
Ecdysone receptor (EcR) agonist. More potent than ecdysone.
Induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form in polytene chromosomes.
Plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in moulting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).
Regulates lipolysis in insects.
Appears in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects.
Used for controlled gene expression in scientific research, agriculture and medicine.
Used for the development of selective insect growth regulators for use as environmentally benign insecticides.
Shows biological effects on mammalian species.
Neurosteroid. Antiepileptic. Acts on the modulatory site of the GABAA receptor and potentiates GABAergic inhibition in rat.
Was shown to stimulate and modulate neutrophil production.
Antidiabetic and antiobesity. Could be used as a nutritional supplement for the prevention and treatment of obesity and obesity-associated disorders.
May protect PC12 cells against CoCl(2)-induced cell injury by inhibiting ROS production and modulating components of the mitochondrial apoptosis pathway.
Does not have potent anabolic properties, however, a muscle-specific increase is observed and genes are identified to provide an explanation for the muscle accretion.
Potential fibrosis antagonist for renal proximal tubule cells. Acts through suppressing post-receptor signaling of TGF-β1 and blocking the expression of Snail.

Product References

20-hydroxyecdysone, what it can do: F. Engelmann; Science 174, 1041 (1971)
Relationship between 'early' and 'late' protein induced by 20-hydroxyecdysone in imaginal wing discs of Drosophila melanogaster: F.Y. Sin; Mol. Biol. Rep. 12, 7 (1987)
Potentiation of GABA-induced inhibition by 20-hydroxyecdysone, a neurosteroid, in cultured rat cortical neurons: S. Tsujiyama, et al.; Jpn. J. Pharmacol. 68, 133 (1995)
Ecdysone signaling cascade and regulation of Drosophila metamorphosis: E.H. Baehrecke, et al.; Arch. Insect Biochem. Physiol. 33, 231 (1996)
Antiepileptic effects of 20-hydroxyecdysone on convulsive seizures in spontaneously epileptic rats: R. Hanaya, et al.; Jpn. J. Pharmacol. 74, 331 (1997)
20-hydroxyecdysone as a human lymphocyte and neutrophil modulator: In vitro evaluation: D.S. Trenin & V.V. Volodin; Arch. Insect Biochem. Physiol. 41, 156 (1999)
Ecdysone receptors and their biological actions: L.M. Riddiford, et al.; Vitam. Horm. 60, 1 (2000)
Ecdysone-regulated puff genes 2000: C.S Thummel; Insect Biochem. Mol. Biol. 32, 113 (2002)
Ecdysone-controlled expression of transgenes: L.D. Graham; Expert Opin. Biol. Ther. 2, 525 (2002)
Non-genomic ecdysone effects and the invertebrate nuclear steroid hormone receptor EcR--new role for an "old" receptor? U. Schlattner, et al.; Mol. Cell Endocrinol. 247, 64 (2006)
20-Hydroxyecdysone decreases weight and hyperglycemia in a diet-induced obesity mice model: P. Kizelsztein, et al.; Am. J. Physiol. Endocrinol. Metab. 296, E433 (2009)
20-hydroxyecdysone reduces insect food consumption resulting in fat body lipolysis during molting and pupation: S. Wang, et al.; J. Mol. Cell Biol. 2, 128 (2010)
Protective effects of 20-hydroxyecdysone on CoCl(2)-induced cell injury in PC12 cells: J. Hu, et al.; J. Cell Biochem. 111, 1512 (2010)
Quinoa extract enriched in 20-hydroxyecdysone protects mice from diet-induced obesity and modulates adipokines expression: A.S. Foucault, et al.; Obesity 20, 270 (2012)
Continuous Infusion of 20-Hydroxyecdysone Increased Mass of Triceps Brachii in C57BL/6 Mice: D.M. Cheng, et al.; Phytother. Res. 27, 107 (2013)
20-hydroxyecdysone attenuates TGF-β1-induced renal cellular fibrosis in proximal tubule cells: T.J. Hung, et al.; J. Diabetes Complications 26, 463 (2012)
Identification of ecdysone hormone receptor agonists as a therapeutic approach for treating filarial infections: A.S. Mhashilkar, et al.; PLOS Negl. Trop. Dis. 10, e0004772 (2016)
Mortality time trends of three subterranean termite species when exposed to 20-Hydroxyecdysone, alone and in combination with noviflumuron: L. Carnohan & NS. Su; J. Econ. Entom. 111, 2312 (2018)

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