beta-Amyrone

Base Information

• Chemical Name: beta-Amyrone
• CAS No.: 638-97-1
• Molecular Formula: C₃₀H₄₈O
• Molecular Weight: 424.711
• ChEMBL ID: CHEMBL461060
• Metabolomics Workbench ID: 135953
• Nikkaji Number: J13.581J
• Pharos Ligand ID: 9G8MTAV9DCTL
• Wikidata: Q104252586
• Mol file: 638-97-1.mol

Synonyms:beta-Amyrone;beta-amyrenone;638-97-1;Beta-Amyrinone;beta-Amyron;CHEMBL461060;(4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one;EX-A6671;HY-N2925;BDBM50242248;AKOS040761409;AC-37065;CS-0023532

Chemical Property of beta-Amyrone

Chemical Property:

• Vapor Pressure: 1.1E-09mmHg at 25°C
• Melting Point: 177-178 °C
• Refractive Index: 1.534
• Boiling Point: 488.3 °C at 760 mmHg
• Flash Point: 202.8 °C
• PSA: 17.07000
• Density: 1.01 g/cm³
• LogP: 8.37710
• Storage Temp.: 2-8°C
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 424.370516150
• Heavy Atom Count: 31
• Complexity: 831

Purity/Quality:

≥98% ^*data from raw suppliers

beta-Amyrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C2C1)C)C)C
• Isomeric SMILES: C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)[C@@H]1CC(CC2)(C)C)C
• Uses: β-Amyron is used as inhibitor of cyclooxygenase and lipoxygenase enzymes to study the structure-activity relationships of pentacyclic triterpenoids.

Technology Process of beta-Amyrone

There total 19 articles about beta-Amyrone 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: 72.0%

beta-amyrin (559-70-6) → β-amyrone (118916-58-8,144666-18-2,638-97-1)

Guidance literature:

With chromium trioxide pyridine; In dichloromethane; for 24h; Ambient temperature;

Reference yield: 35.0%

beta-amyrin (559-70-6) → β-amyrone (118916-58-8,144666-18-2,638-97-1) + 3,11-dioxo-β-amyrene (2935-32-2) + 3β,11α-dihydroxy-olean-12-ene (5282-14-4) + 3β-hydroxy-olean-9(11),12-diene (94530-87-7)

Guidance literature:

With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; iodosylbenzene; In dichloromethane; at 20 ℃; for 5h;

Reference yield:

olean-12-ene-3-ol (107596-78-1) → β-amyrone (118916-58-8,144666-18-2,638-97-1)

Guidance literature:

With Jones reagent; In acetone;

DOI:10.21577/0103-5053.20160219

upstream raw materials:

beta-amyrin

oleana-1,12-dien-3-one

1,3-Dioxoolean-12-en

3-Methoxy-1-oxo-oleanadien-(2,12)

Downstream raw materials:

β-amyr-1-en-3-one

A-nor-β-amyr-1,2-dione

beta-amyrin

3α-hydroxyolean-12-ene

Refernces

• 1、 Calixto, Nivea O.,Cordeiro, Millena S.,Giorno, Thais B. S.,Oliveira, Gibson G.,Lopes, Norberto P.,Fernandes, Patricia D.,Pinto, Angelo C.,Rezende, Claudia M.. "Chemical constituents of Psychotria nemorosa gardner and antinociceptive activity". . p. 707 - 723. Retrieved 2017/03/31.
• 2、 Chauhan,Mohapatra,Mamta,Parkash,Azam. "Biomimetic oxidation of 3β-hydroxy-olean-12-ene and its acetoxy derivative with monooxygen donors catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane". . p. 183 - 189. Retrieved 2007/10/03.