Malabaricone C

Base Information

• Chemical Name: Malabaricone C
• CAS No.: 63335-25-1
• Molecular Formula: C21H26 O5
• Molecular Weight: 358.434
• NSC Number: 287968
• UNII: C9K53R3PRN
• DSSTox Substance ID: DTXSID40212721
• Nikkaji Number: J19.530H
• Wikidata: Q27137360
• Pharos Ligand ID: 24Q1KRVCZW91
• Metabolomics Workbench ID: 38765
• ChEMBL ID: CHEMBL524100
• Mol file: 63335-25-1.mol

Synonyms:malabaricone C

Chemical Property of Malabaricone C

Chemical Property:

• PSA: 97.99000
• LogP: 4.66510
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 358.17802393
• Heavy Atom Count: 26
• Complexity: 403

Purity/Quality:

99% ^*data from raw suppliers

Malabaricone C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)C(=O)CCCCCCCCC2=CC(=C(C=C2)O)O)O
• Description: Malabaricone C is a diarylnonanoid that has been found in Myristica and has diverse biological activities. It scavenges 59.9% of 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals when used at a concentration of 7 μg/ml. Malabaricone C is active against S. aureus, B. subtilis, and C. albicans in vitro (MICs = 2-32 μg/ml). It is cytotoxic to A549, HL-60, and MCF-7 cells (IC50s = 12.3, 46.1, and 10.8 μM, respectively). Malabaricone C inhibits sphingomyelin synthase 1 (SMS1) and SMS2 activity in cell lysates (IC50s = 3 and 1.5 μM, respectively). It decreases body weight gain, hepatic steatosis, and hepatic and plasma triglyceride levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 0.1% in the diet.

Technology Process of Malabaricone C

There total 15 articles about Malabaricone C 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: 97.0%

1-(2,6-Dihydroxyphenyl)-9-(3,4-dimethoxyphenyl)nonan-1-one (133839-80-2) → Malabaricone C (63335-25-1)

Guidance literature:

With boron tribromide; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.39.18

Reference yield: 78.0%

1-(2,6-dimethoxyphenyl)-9-(3,4-dimethoxyphenyl)nonan-1-one → Malabaricone C (63335-25-1) + 9-(3,4-dihydroxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)nonan-1-one

Guidance literature:

With boron tribromide; In dichloromethane; at -40 - 20 ℃; for 18h;

DOI:10.1021/acs.jnatprod.6b01119

Reference yield:

1-bromo-6-benzyloxyhexane (54247-27-7) → Malabaricone C (63335-25-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / 2 h / 140 °C

2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min

3: 83 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature

4: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min

5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min

6: 91 percent / p-toluenesulfonic acid / benzene / 1 h / Heating

7: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature

8: 97 percent / boron tribromide / CH₂Cl₂ / 0.17 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; potassium tert-butylate; hydrogen; boron tribromide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; dichloromethane; acetone; benzene;

DOI:10.1248/cpb.39.18

upstream raw materials:

1-(2,6-Dihydroxyphenyl)-9-(3,4-dimethoxyphenyl)nonan-1-one

2,6-dihydroxylacetophenone

1-bromo-6-benzyloxyhexane

1-[2-(benzyloxy)-6-hydroxyphenyl]ethanone

Refernces

• 1、 Pham, Van Cuong,Jossang, Akino,Sévenet, Thierry,Bodo, Bernard. "Cytotoxic acylphenols from Myristica maingayi". . p. 1707 - 1713. Retrieved 2007/10/03.