Lupenone

Base Information

• Chemical Name: Lupenone
• CAS No.: 1617-70-5
• Molecular Formula: C30H48 O
• Molecular Weight: 424.711
• Hs Code.: 29142990
• European Community (EC) Number: 834-243-6
• Nikkaji Number: J82.270A
• Wikidata: Q27136299
• Metabolomics Workbench ID: 138507
• ChEMBL ID: CHEMBL486393
• Mol file: 1617-70-5.mol

Synonyms:lupenone

Chemical Property of Lupenone

Chemical Property:

• Vapor Pressure: 1.38E-09mmHg at 25°C
• Melting Point: 165-167℃
• Boiling Point: 485.7°Cat760mmHg
• Flash Point: 201.6°C
• PSA: 17.07000
• Density: 0.973g/cm³
• LogP: 8.23300
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 9.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 424.370516150
• Heavy Atom Count: 31
• Complexity: 807

Purity/Quality:

98%,99%, ^*data from raw suppliers

Lupenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CCC(=O)C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)C)C
• Uses: Lupenone is a lupane triterpenoid with antioxidant and anticholinesterase activity. It also a potential protein tyrosine phosphatase 1B (PTP1B) inhibitor.

Technology Process of Lupenone

There total 25 articles about Lupenone 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: 91.0%

lupenol (545-47-1) → lupenone (1617-70-5)

Guidance literature:

With Jones reagent; acetic acid; In chloroform; at 20 ℃; for 0.166667h; Cooling with ice;

DOI:10.1016/j.bmcl.2014.05.032

Reference yield: 90.0%

lup-20(29)-en-3-oxime (3607-91-8) → lupenone (1617-70-5)

Guidance literature:

With Montmorillonite K-10 clay; pyridinium chlorochromate; for 0.0333333h; microwave irradiation;

Reference yield: 40.0%

Glochidone (6610-55-5) → lupenol (545-47-1) + lupenone (1617-70-5) + 3-epilupeol (33869-84-0,55870-42-3,101627-40-1,107596-77-0,545-47-1,4439-99-0)

Guidance literature:

With potassium hydroxide; In diethylene glycol; for 2h; Heating;

DOI:10.1016/S0040-4020(01)96647-5

upstream raw materials:

lupenol

Glochidone

3,3-ethylenedioxylup-20⁽²⁹⁾-ene

lupeol

Downstream raw materials:

lupenol

3-epilupeol

lupanol

Glochidone

Refernces

• 1、 Wijeratne, Dharmassree B. T.,Kumar, Vijaya,Sultanbawa, M. Uvais S.. "3-Oxolup-20(29)-en-30-al, a New Lupane from Gymnosporia emarginata (Celastraceae)". . p. 2724 - 2726. Retrieved 1981.
• 2、 Lao,Fujimoto,Tatsuno. "Studies on the constituents of Artemisia argyi LEVL et VANT". . p. 723 - 727. Retrieved 1984.
• 3、 Rao, S. Devendra,Rao, B. Nageswara,Devi, P. Uma,Rao, A. Karteek. "Isolation of lupeol, design and synthesis of lupeol derivatives and their biological activity". . p. 173 - 180. Retrieved 2017.
• 4、 Biedebach. "-". . . Retrieved 1943.
• 5、 Castro, María Julia,Richmond, Victoria,Faraoni, María Belén,Murray, Ana Paula. "Oxidation at C-16 enhances butyrylcholinesterase inhibition in lupane triterpenoids". . p. 301 - 309. Retrieved 2018/05/28.