Sakuranetin

Base Information

• Chemical Name: Sakuranetin
• CAS No.: 2957-21-3
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.284
• European Community (EC) Number: 220-980-5
• UNII: 3O38P61299
• Nikkaji Number: J7.652J
• Wikipedia: Sakuranetin
• Wikidata: Q3459689
• RXCUI: 2263158
• Pharos Ligand ID: AWR963QMT467
• Metabolomics Workbench ID: 27722
• ChEMBL ID: CHEMBL448297
• Mol file: 2957-21-3.mol

Synonyms:naringenin 7-methyl ether;sakuranetin

Chemical Property of Sakuranetin

Chemical Property:

• Melting Point: 153-154 °C
• Boiling Point: 555.9 °C at 760 mmHg
• PKA: 7.42±0.40(Predicted)
• Flash Point: 212.4 °C
• PSA: 75.99000
• Density: 1.37 g/cm³
• LogP: 2.81290
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

≥98% ^*data from raw suppliers

Sakuranetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
• Isomeric SMILES: COC1=CC(=C2C(=O)C[C@H](OC2=C1)C3=CC=C(C=C3)O)O
• General Description: Sakuranetin is a bioactive flavanone derivative, specifically a 7-O-methylated form of naringenin, synthesized through regioselective deacetylation of naringenin triacetate at the C-7 position followed by methylation. SAKURANETIN, along with its structural analogs, holds significance due to its biological activity and potential applications in pharmaceutical and chemical research.

Technology Process of Sakuranetin

There total 13 articles about Sakuranetin 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + naringenin (480-41-1) → (-)-(S)-sakuranetin (520-29-6,2957-21-3,17784-36-0,118244-13-6)

Guidance literature:

In methanol; diethyl ether; at 20 ℃; for 6h;

DOI:10.1016/j.phytochem.2005.04.031

Reference yield: 76.0%

dimethyl sulfate (77-78-1) + naringenin (480-41-1) → (-)-(S)-sakuranetin (520-29-6,2957-21-3,17784-36-0,118244-13-6)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃; for 12h;

DOI:10.1016/j.bmc.2020.115798

Reference yield: 31.8%

naringenin (480-41-1) + methyl iodide (74-88-4) → (-)-(S)-sakuranetin (520-29-6,2957-21-3,17784-36-0,118244-13-6)

Guidance literature:

With sodium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 0.0833333h;

upstream raw materials:

5,4′-dihydroxy-7-methoxyflavanone 5-O-β-D-glucopyranoside

diazomethane

naringenin

naringin

Downstream raw materials:

Acetic acid (S)-2-(4-acetoxy-phenyl)-7-methoxy-4-oxo-chroman-5-yl ester

naringenin

Refernces

Simple synthesis of sakuranetin and selinone via a common intermediate, utilizing complementary regioselectivity in the deacetylation of naringenin triacetate

10.1248/cpb.c16-00190

The research presents a simple synthesis of sakuranetin and selinone, two biologically active compounds, utilizing the regioselective deacetylation of naringenin triacetate. Imidazole was used to selectively deacetylate naringenin triacetate at the C-7 position, leading to the formation of an intermediate that was subsequently methylated to produce sakuranetin. For the synthesis of selinone, the same starting material was subjected to transesterification with 2-propanol in the presence of Candida antarctica lipase B, resulting in selective deacetylation at the C-4′ position. This intermediate was then prenylated under Mitsunobu conditions to yield selinone. The study highlights the importance of these chemicals in achieving the desired regioselectivity and in the overall synthesis of these bioactive compounds.