20-Hydroxyecdysone

Base Information

• Chemical Name: 20-Hydroxyecdysone
• CAS No.: 5289-74-7
• Molecular Formula: C27H44O7
• Molecular Weight: 480.642
• Hs Code.: 29372900
• European Community (EC) Number: 811-097-1
• UNII: 779A7KPL0Y
• DSSTox Substance ID: DTXSID5040388
• Nikkaji Number: J13.425B
• Wikipedia: 20-Hydroxyecdysone
• Wikidata: Q423338
• Metabolomics Workbench ID: 34497
• ChEMBL ID: CHEMBL224128
• Mol file: 5289-74-7.mol

Synonyms:20 Hydroxyecdysone;20-Hydroxyecdysone;Beta Ecdysone;Beta-Ecdysone;Crustecdysone;Ecdysterone

Chemical Property of 20-Hydroxyecdysone

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 8.7E-23mmHg at 25°C
• Melting Point: 242-244 °C
• Refractive Index: 1.596
• Boiling Point: 702.1 °C at 760 mmHg
• PKA: 14.13±0.70(Predicted)
• Flash Point: 392.4 °C
• PSA: 138.45000
• Density: 1.28 g/cm³
• LogP: 1.85400
• Storage Temp.: 2-8°C
• Solubility.: alcohol: soluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 480.30870374
• Heavy Atom Count: 34
• Complexity: 869

Purity/Quality:

98%, ^*data from raw suppliers

Beta-Ecdysterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
• Isomeric 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
• Recent ClinicalTrials: Testing the Efficacy and Safety of BIO101 for the Prevention of Respiratory Deterioration in COVID-19 Patients
• Recent EU Clinical Trials: Adaptive design phase 2 to 3, randomized, double- blind, multicenter, to evaluate the safety, efficacy, pharmacokinetics and pharmacodynamics of BIO101 in the prevention of the respiratory deterioration in hospitalized patients with COVID-19 pneumonia (severe stage)
• Uses: insect molting hormone 20-Hydroxyecdysone has been used:in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sextain Schneider′s medium to reproduce ex-vivo imaginal disc eversionas a supplement in Mcl8 medium for culturing Drosophila wing imaginal discs

Technology Process of 20-Hydroxyecdysone

There total 51 articles about 20-Hydroxyecdysone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione → 20-Hydroxyecdysone (5289-74-7)

Guidance literature:

With sodium hydroxide; In methanol; for 2.5h; Heating;

DOI:10.1002/hlca.19870700320

Reference yield: 82.0%

(2S,3R,5R,9R,10R,13R,14S,17S)-14-Hydroxy-17-((1R,2R)-5-hydroxy-1,2-diisopropoxy-1,5-dimethyl-hexyl)-2,3-diisopropoxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one → 20-Hydroxyecdysone (5289-74-7)

Guidance literature:

With lithium; In tetrahydrofuran; ammonia; for 1h;

DOI:10.1002/hlca.19870700320

Reference yield: 80.0%

(20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one (135024-06-5) → 20-Hydroxyecdysone (5289-74-7) + (20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one (123238-67-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4020(01)80901-7

upstream raw materials:

20-hydroxyecdysone-2,3,22-triacetate

22-Dehydro-20-hydroxyecdysone

(20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one

Downstream raw materials:

Poststerone

calonysterone

20-Hydroxyecdysone-2-acetate

20-Hydroxyecdysone-22-acetate

Refernces

• 1、 Baltaev, U. A.,Darmograi, V. N.,Abubakirov, N. K.. "PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. ECDYSTERONE 20-O-BENZOATE FROM Silene tatarica". . p. 706 - 708. Retrieved 1987.
• 2、 Nomura, Keiko,Fujimoto, Yoshinori. "Mechanism of C-2 hydroxylation during the biosynthesis of 20- hydroxyecdysone in Ajuga hairy roots". . p. 344 - 348. Retrieved 2000.
• 3、 Savchenko,Kostyleva,Kachala,Khalilov,Odinokov. "A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids". . p. 995 - 998. Retrieved 2013/09/02.
• 4、 Suksamrarn, Apichart,Tanachatchairatana, Tanud,Sirigarn, Chana. "Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite". . p. 6033 - 6037. Retrieved 2007/10/03.