Naringenin triacetate

Base Information

• Chemical Name: Naringenin triacetate
• CAS No.: 3682-04-0
• Molecular Formula: C21H18O8
• Molecular Weight: 398.36300
• Hs Code.: 2932999099
• Mol file: 3682-04-0.mol

Synonyms:

Chemical Property of Naringenin triacetate

Chemical Property:

• PSA: 105.20000
• LogP: 3.16900

Purity/Quality:

99% ^*data from raw suppliers

NaringeninTriacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Naringenin triacetate

There total 3 articles about Naringenin triacetate 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: 83.0%

acetic anhydride (108-24-7) + naringenin (480-41-1) → (S)-2-(4-acetoxyphenyl)-4-oxochromane-5,7-diyl diacetate (3682-04-0,73111-01-0,93860-46-9)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 45 ℃; for 1h;

DOI:10.1080/14786419.2022.2031186

Reference yield: 39.0%

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) + acetic anhydride (108-24-7) → (S)-2-(4-acetoxyphenyl)-4-oxochromane-5,7-diyl diacetate (3682-04-0,73111-01-0,93860-46-9)

Guidance literature:

With pyridine; at 15 ℃; for 12h;

Reference yield:

→ (S)-2-(4-acetoxyphenyl)-4-oxochromane-5,7-diyl diacetate (3682-04-0,73111-01-0,93860-46-9)

Guidance literature:

1.) Isolation aus d. Extrakt v. Ribes sanguineum, 2.) Chromatogr. nach Acetylierung (Ac2O/Py.);

upstream raw materials:

acetic anhydride

naringenin

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Downstream raw materials:

2-(4-acetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate

sophoraflavanone B

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.