Ryanodine

Base Information

• Chemical Name: Ryanodine
• CAS No.: 15662-33-6
• Deprecated CAS: 8047-13-0,1580-06-9,25800-57-1,15800-60-9
• Molecular Formula: C25H35 N O9
• Molecular Weight: 493.554
• European Community (EC) Number: 239-732-2
• DSSTox Substance ID: DTXSID0032574
• Metabolomics Workbench ID: 53415
• Wikidata: Q59851226
• Wikipedia: Ryanodine
• Mol file: 15662-33-6.mol

Synonyms:Ryanodine

Chemical Property of Ryanodine

Chemical Property:

• Appearance/Colour: White solid.
• Melting Point: 219-220 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 714.2°Cat760mmHg
• PKA: 10.66±0.70(Predicted)
• Flash Point: 385.7°C
• PSA: 172.70000
• Density: 1.55g/cm³
• LogP: -0.18760
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 493.23118169
• Heavy Atom Count: 35
• Complexity: 1010

Purity/Quality:

99%, ^*data from raw suppliers

Ryanodine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnN
• Hazard Codes: Xn,N
• Statements: 21/22-50/53
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C3(CC4(C5(C(C(C3(C5(C2(C1O)O4)O)O)OC(=O)C6=CC=CN6)(C(C)C)O)C)O)C)O
• Isomeric SMILES: C[C@H]1CC[C@@]2([C@@]3(C[C@]4([C@@]5([C@]([C@H]([C@@]3([C@]5([C@]2([C@@H]1O)O4)O)O)OC(=O)C6=CC=CN6)(C(C)C)O)C)O)C)O
• Description: Ryania insecticide is the ground stem wood of the tropical tree Ryania speciosa Vahl., and it contains over a dozen of several structurally related alkaloids. Nowadays, this botanical preparation is of minor importance, but one of its major ingredients, ryanodine, is a widely used pharmacological tool in studies of the calcium release channels in sarcoplasmic reticulum membranes of skeletal and cardiac muscle of both insects and mammals (11,12).
• Uses: Insecticide. Ryanodine is a potent inhibitor of Ca2+ release from sarcoplasmic reticulum with potential application towards the treatment of huntingtons disease.

Technology Process of Ryanodine

There total 29 articles about Ryanodine 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: 76.0%

C39H45NO9 → ryanodine (15662-33-6,97588-26-6,150736-85-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 48h; under 760.051 Torr;

DOI:10.1002/chem.201503641

Reference yield:

15-benzylryanodine → ryanodine (15662-33-6,97588-26-6,150736-85-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 3.5h; under 760.051 Torr;

DOI:10.1248/cpb.c16-00214

Reference yield:

Dehydroryanodine (94513-55-0) → ryanodine (15662-33-6,97588-26-6,150736-85-9) + 9-Epiryanodine

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1039/c39840001265

upstream raw materials:

Dehydroryanodine

Downstream raw materials:

N-butylryanodine

10-O-(3-benzoyloxycarbamoylpropionyl)ryanodine

N-benzylryanodine

C₂₅H₃₅NO₁₁

Refernces

• 1、 Masuda, Kengo,Nagatomo, Masanori,Inoue, Masayuki. "Chemical conversion of ryanodol to ryanodine". . p. 874 - 879. Retrieved 2016/07/14.
• 2、 Waterhouse, Andrew L.,Holden, Ian,Casida, John E.. "Ryanoid Insecticides: Structural Examination by Fully Coupled Two-dimensional 1H-13C Shift Correlation Nuclear Magnetic Resonance Spectroscopy". . p. 1011 - 1016. Retrieved 2007/10/02.