Gingerenone A

Base Information

• Chemical Name: Gingerenone A
• CAS No.: 128700-97-0
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419
• ChEMBL ID: CHEMBL1086746
• DSSTox Substance ID: DTXSID50873741
• Metabolomics Workbench ID: 46938
• Nikkaji Number: J282.842A
• Wikidata: Q27106727
• Mol file: 128700-97-0.mol

Synonyms:gingerenone A

Chemical Property of Gingerenone A

Chemical Property:

• Vapor Pressure: 1.19E-13mmHg at 25°C
• Boiling Point: 571.3°Cat760mmHg
• Flash Point: 200.3°C
• PSA: 75.99000
• Density: 1.183g/cm³
• LogP: 3.80570
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 356.16237386
• Heavy Atom Count: 26
• Complexity: 450

Purity/Quality:

≥98% ^*data from raw suppliers

GingerenoneA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCC=CC(=O)CCC2=CC(=C(C=C2)O)OC)O
• Isomeric SMILES: COC1=C(C=CC(=C1)CC/C=C/C(=O)CCC2=CC(=C(C=C2)O)OC)O
• Uses: Gingerenone A is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders.

Technology Process of Gingerenone A

There total 7 articles about Gingerenone A 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: 84.0%

hexahydrocurcumin (36062-05-2,39886-84-5,93559-28-5,100667-55-8) → (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one (79067-88-2,81569-02-0,128700-97-0)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 2h; Heating;

Reference yield: 70.0%

4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5) + 3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde (80638-48-8) → (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one (79067-88-2,81569-02-0,128700-97-0)

Guidance literature:

With DIMCARB; at 20 ℃; for 96h;

DOI:10.1039/c9ob02662b

Reference yield:

curcumin (458-37-7) → (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one (79067-88-2,81569-02-0,128700-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 136 mg / H₂ / Pd/C / ethanol

2: 75 percent / p-TsOH*H₂O / benzene / Heating

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; benzene;

DOI:10.1016/S0031-9422(02)00618-0

upstream raw materials:

hexahydrocurcumin

curcumin

1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione

curcumin

Downstream raw materials:

hirsutenone

Refernces

• 1、 -. "FOOD COMPOSITION FOR PREVENTING OBESITY, PHARMACEUTICAL COMPOSITION FOR TREATING OBESITY, AND ANIMAL MEDICINE FOR TREATING OBESITY, CONTAINING GINGERNONE A". Sheet 1. . Retrieved 2016/04/10.
• 2、 Venkateswarlu,Ramachandra,Rambabu,Subbaraju. "Synthesis of gingerenone-A and hirsutenone". . p. 495 - 497. Retrieved 2007/10/03.