Sedanolide

Base Information

• Chemical Name: Sedanolide
• CAS No.: 6415-59-4
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.274
• ChEMBL ID: CHEMBL2165230
• DSSTox Substance ID: DTXSID001027843
• Metabolomics Workbench ID: 46553
• Nikkaji Number: J1.462.040K
• Wikidata: Q21099594
• Wikipedia: Sedanolide
• Mol file: 6415-59-4.mol

Synonyms:neocnidilide;neocnidilide, (cis)-isomer;neocnidilide, (trans)-isomer;neocnidilide, cis-(-)-isomer;sedanolide

Chemical Property of Sedanolide

Chemical Property:

• Melting Point: 30～31℃
• Boiling Point: 342.0±11.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.03
• LogP: 2.82850
• Solubility.: insoluble in H2O; ≥52.8 mg/mL in EtOH; ≥6.65 mg/mL in DMSO
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 194.130679813
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

99%, ^*data from raw suppliers

Trans-Sedanolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C2CCCC=C2C(=O)O1
• Uses: Sedanolide is a natural phthalide isolates from seed oil of Umbelliferae family. It induces the expression of glutathione S-transferase and reduces chemical induced carcinogenesis in mice.

Technology Process of Sedanolide

There total 48 articles about Sedanolide 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: 75.0%

Imidazole-1-carbothioic acid O-((3R,3aR,4R)-3-butyl-1-oxo-1,3,3a,4,5,6-hexahydro-isobenzofuran-4-yl) ester → isocnidilide (2550-44-9,3553-29-5,3861-62-9,4567-33-3,6415-59-4,114923-85-2,114923-86-3,124815-25-4,132697-21-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2.5h; Heating;

DOI:10.1021/jo00007a017

Reference yield:

C12H20O3 → (+/-)-neocnidilide (2550-44-9,3553-29-5,3861-62-9,4567-33-3,6415-59-4,114923-85-2,114923-86-3,124815-25-4,132697-21-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.035

Reference yield:

C12H20O3 → isocnidilide (2550-44-9,3553-29-5,3861-62-9,4567-33-3,6415-59-4,114923-85-2,114923-86-3,124815-25-4,132697-21-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.035

upstream raw materials:

pentanal

N-methyl-1-cyclohexene-1-carboxamide

cyclohex-1-enecarbonitrile

4-hydroxy-cis-neocnidilide

Refernces

• 1、 Oguro, Daichi,Watanabe, Hidenori. "Synthesis and sensory evaluation of all stereoisomers of sedanolide". experimental part. p. 777 - 781. Retrieved 2011/03/19.