Ecdysone

Base Information

• Chemical Name: Ecdysone
• CAS No.: 3604-87-3
• Molecular Formula: C27H44O6
• Molecular Weight: 464.643
• Hs Code.: 2937290090
• European Community (EC) Number: 222-760-4
• UNII: RH692X7B7B
• Nikkaji Number: J8.177I
• Wikipedia: Ecdysone
• Wikidata: Q139085
• Metabolomics Workbench ID: 34498
• ChEMBL ID: CHEMBL549300
• Mol file: 3604-87-3.mol

Synonyms:Ecdysone;Molting Hormone

Chemical Property of Ecdysone

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.26E-18mmHg at 25°C
• Melting Point: 242 °C
• Refractive Index: 1.582
• Boiling Point: 632 °C at 760 mmHg
• PKA: 14.07±0.70(Predicted)
• Flash Point: 350 °C
• PSA: 118.22000
• Density: 1.22 g/cm³
• LogP: 2.73910
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Very Slightly, Heated)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 464.31378912
• Heavy Atom Count: 33
• Complexity: 821

Purity/Quality:

99%, ^*data from raw suppliers

Ecdysone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O
• Uses: α-Ecdysone is a steroidal prohormone.

Technology Process of Ecdysone

There total 23 articles about Ecdysone 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:

2,22-dideoxyecdysone (41408-38-2) → 20-Hydroxyecdysone (5289-74-7) + ecdysone (3604-87-3) + 22-Deoxyecdysone (34209-85-3) + 2-deoxyecdysone (72630-20-7,77732-73-1,31575-91-4)

Guidance literature:

With Locusta migratoria; at 33 ℃; for 6h; Product distribution; tissue distr. of C₂₂ hydroxylase;

DOI:10.1016/S0040-4020(01)85918-4

Reference yield:

26-hydroxyecdysone (52717-49-4) → 20-Hydroxyecdysone (5289-74-7) + ecdysone (3604-87-3) + 3-epi-26-hydroxyecdysone (75319-59-4) + Coronatasterone (5289-74-7,7703-93-7,22678-71-3,22678-72-4,35241-82-8,84580-28-9,123238-67-5,54053-93-9) + 3-epi-20,26-dihydroxyecdysone (71939-17-8) + 20,26-dihydroxyecdysone (19458-46-9)

Guidance literature:

metabolism after injection into Pieris brassicae (Lepidoptera) pharate pupae, 3H labeled study;

DOI:10.1016/0039-128X(80)90018-5

Reference yield:

3-((2R,3S,4aR,4bS,6aS,6bR,7S,8R,9aS,10aS,10bR,12aS)-2,3-Diacetoxy-4a,6a,7-trimethyl-12-oxo-octadecahydro-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-propionic acid methyl ester (77260-31-2) → ecdysone (3604-87-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 50 percent / Br₂ / HBr / acetic acid

2: 90 percent / SeO₂ / dioxane / 80 °C / Heating

3: 72 percent / (CF₃CO)2O, SeO₂ (trace) / pyridine / 0 °C

4: Zn, acetic acid / acetic acid / Heating

5: H₂ / Pd-C / ethyl acetate

6: O₂, Rose Bengal / methanol / Irradiation

7: NaI, AcOH / methanol

With selenium(IV) oxide; hydrogen; bromine; oxygen; rose bengal; acetic acid; trifluoroacetic anhydride; sodium iodide; zinc; palladium on activated charcoal; hydrogen bromide; In 1,4-dioxane; pyridine; methanol; acetic acid; ethyl acetate;

DOI:10.1016/S0040-4039(00)77848-8

upstream raw materials:

Acetic acid (2S,3R,5S,9R,10R,13R,14S,17R)-3-acetoxy-14-hydroxy-10,13-dimethyl-6-oxo-17-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

2,22-dideoxyecdysone

(20S,22R)-2β,3β,22-triacetoxy-14α,25-dihydroxy-5β-cholest-7-en-6-one

ecdysone-22-phosphate

Downstream raw materials:

20-Hydroxyecdysone

3-epi-26-hydroxyecdysone

26-hydroxyecdysone

Coronatasterone

Refernces

SIDE CHAIN MODIFIED STEROLS AS PROBES INTO INSECT MOLTING HORMONE METABOLISM. II: SYNTHESIS OF MONOFLUOROCHOLESTEROLS

10.1016/0039-128X(83)90018-1

The research focuses on the synthesis and bioassay of monofluorinated cholesterols as potential inhibitors of hydroxylation events in ecdysone biogenesis, a key process in insect molting. The study involves the preparation of C-20, C-22, C-24, and C-25 monofluorinated cholesterols, with the aim of disrupting specific hydroxylations in the cholesterol side chain that are crucial for ecdysone production. The chemicals used in the research include various reagents such as isohexylmagnesium bromide, diethylaminosulfur trifluoride (DAST), and p-toluenesulfonic acid (TsOH) for synthesis, as well as solvents like tetrahydrofuran (THF) and methylene chloride. The study also involves the use of radioactive labeling with [26-14C] for metabolic studies. The bioassays conducted on Manduca sexta larvae showed that while most monofluorinated compounds had little effect on larval growth and development, the 24-fluorocholesterol isomer caused significant growth retardation and increased mortality.