20-Hydroxyecdysone (Crustecdysone)

Alias: B-ecdysone; Commisterone; B-ecdysone; Crustecdysone; Commisterone Ecdysterone; 20E
Cat No.:V2376 Purity: ≥98%
20-Hydroxyecdysone (also known as B-ecdysone, Crustecdysone, Commisterone Ecdysterone, 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods.
20-Hydroxyecdysone (Crustecdysone) Chemical Structure CAS No.: 5289-74-7
Product category: Caspase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

20-Hydroxyecdysone (also known as B-ecdysone, Crustecdysone, Commisterone Ecdysterone, 20E) is an ecdysteroid hormone that is present in nature and regulates the ecdysis (moulting) and metamorphosis of arthropods. In H4IIE cell culture, 20-Hydroxyecdysone treatment reduces the expression of the enzymes glucose-6-phosphatase (G6Pase) and phosphoenolpyruvate carboxykinase (PEPCK), lowers glucose production, and increases Akt2 phosphorylation that is responsive to the phosphoinositide-3 kinase pathway inhibitor LY-294002. Treatment with 20-hydroxyecdysone either before or after exposure to CoCl2 significantly reduces CoCl2-induced cellular damage.

Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
ln Vitro
20-Hydroxyecdysone treatment in H4IIE cell culture reduces the expression of glucose-6-phosphatase (G6Pase) and phosphoenolpyruvate carboxykinase (PEPCK), lowers glucose production, and increases Akt2 phosphorylation sensitive to the phosphoinositide-3 kinase pathway-specific inhibitor LY-294002.[1] Treatment with 20-hydroxyecdysone either before or after exposure to CoCl2 significantly lessens the cellular damage caused by CoCl2. 20-Hydroxyecdysone significantly decreases the production of reactive oxygen species (ROS) that CoCl2-induced, as well as the depolarization of the mitochondrial membrane, the release of cytochrome c into the cytosol, the Bax/Bcl-2 ratio, and the activation of caspase-3 that CoCl2-induced.[2] With an IC50 of 31.8 µM, 20-hydroxyecdysone prevents NF-κB activation in HeLa cells that have been persistently transfected with an IL-6-bound reporter gene.[3] The apoptotic genes Apaf-1, Nedd2 like1, Nedd2 like2, ICE1, ICE3, ICE5, Arp, and IAP are upregulated when 20-Hydroxyecdysone is administered to larval fat body tissues in vitro.[4] 20-hydroxyecdysone reverses TGF-1-induced upregulation of Smad7 and upregulation of intracellular and extracellular fibronectin. 20-Hydroxyecdysone also significantly reduces the effects of TGF-1 on the upregulation of Smad2/3 and pSmad2/3, as well as the downregulation of E-Cadherin. Additionally, TGF-1-induced increases in Snail expression are sharply suppressed by 20-hydroxyecdysone.[5]
ln Vivo
In C57BL/6J mice fed a high-fat diet, oral administration of 20-Hydroxyecdysone (10 mg/kg/day for 13 weeks) reduces body weight gain and body fat mass significantly when compared to untreated animals. It also improves obesity and insulin resistance. In addition, 20-hydroxyecdysone therapy significantly reduces plasma insulin levels and glucose tolerance. Along with these modifications, visceral fat tissue produces more adiponectin and PEPCK and G6Pase are expressed less strongly in the liver. [1] Injection of 20-Hydroxyecdysone into day 2 of fifth instar larvae significantly induces apoptosis and upregulates apoptotic genes in the fat body of the silkworm, Bombyx mori, after 6 hours of treatment.[4]
Animal Protocol
Formulated in vehicle solution (10% DMSO in corn oil); 10 mg/kg/day; Oral administration
Male C57BL/6J mice fed a high-fat diet
References

[1]. Am J Physiol Endocrinol Metab . 2009 Mar;296(3):E433-9.

[2]. J Cell Biochem . 2010 Dec 15;111(6):1512-21. doi: 10.1002/jcb.22877.

[3]. J Pharm Pharmacol . 2011 Nov;63(11):1483-95.

[4]. Arch Insect Biochem Physiol . 2012 Apr;79(4-5):207-19.

[5]. J Diabetes Complications . 2012 Nov-Dec;26(6):463-9.

[6]. Phytother Res . 2013 Jan;27(1):107-11.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H44O7
Molecular Weight
480.63
Exact Mass
480.3087
Elemental Analysis
C, 67.47; H, 9.23; O, 23.30
CAS #
5289-74-7
Related CAS #
5289-74-7
Appearance
Solid powder
SMILES
C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O
InChi Key
NKDFYOWSKOHCCO-YPVLXUMRSA-N
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
Chemical Name
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms
B-ecdysone; Commisterone; B-ecdysone; Crustecdysone; Commisterone Ecdysterone; 20E
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~96 mg/mL (~199.7 mM)
Water: <1 mg/mL
Ethanol: ~96 mg/mL (~199.7 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 1% DMSO +30% polyethylene glycol+1% Tween 80 : 30 mg/mL

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0806 mL 10.4030 mL 20.8060 mL
5 mM 0.4161 mL 2.0806 mL 4.1612 mL
10 mM 0.2081 mL 1.0403 mL 2.0806 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04827537 Active
Recruiting
Drug: Placebo Oral
Drug: Metronidazole Oral
Giardia Lamblia Infection Research Institute of
Epidemiology, Microbiology
and Infectious Diseases,
Uzbekistan
January 1, 2021 Phase 2
Phase 3
NCT03452488 Completed Drug: BIO101
Drug: Placebo oral capsule
Sarcopenia
Muscle Weakness
Biophytis May 24, 2018 Phase 2
Biological Data
  • 20-Hydroxyecdysone. Phytother Res . 2013 Jan;27(1):107-11.
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