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:

≥98% ^*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
• General Description: Ryanodine is a naturally occurring alkaloid that acts as a potent modulator of the ryanodine receptor (RyR), a calcium channel critical for intracellular calcium release in muscle and nerve cells. It is widely studied for its insecticidal properties, as it disrupts calcium homeostasis in pests, leading to paralysis and death. RYANODINE and its derivatives, such as those explored in the study of phthalamides, are being investigated for their potential as environmentally friendly insecticides due to their selective targeting of insect RyRs. Structure-activity relationship (SAR) studies highlight the importance of specific chemical groups, such as fluorine substitutions, in enhancing insecticidal efficacy. Ryanodine and its analogs thus represent a promising class of compounds for developing novel pest control agents.

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

Cbz-glycylryanodine

Refernces

Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel

10.1016/j.bmc.2014.09.052

The study focuses on the synthesis, insecticidal activities, and structure-activity relationships (SAR) of novel phthalamides targeting calcium channels, specifically the ryanodine receptor. These compounds were designed to serve as environmentally friendly insecticides. The research involved the design and synthesis of three series of phthalamides, which included compounds with a heptafluoroisopropyl group, low fluorine atoms group, and non-fluorine group. A total of 35 novel structures were obtained and tested for their insecticidal activities against the oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). The study revealed that most of these compounds exhibited moderate to high insecticidal activities at the tested concentrations. The structure-activity relationship was discussed in detail to understand the role of different chemical groups on the insecticidal efficacy. Additionally, the study employed calcium-imaging techniques to investigate the effects of certain compounds on intracellular calcium ion concentration, indicating their potential as modulators of the insect ryanodine receptor. The findings provide valuable insights for the development of new, environmentally friendly insecticides targeting calcium channels.