semivioxanthin

Base Information

• Chemical Name: semivioxanthin
• CAS No.: 70477-26-8
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• Mol file: 70477-26-8.mol

Synonyms:(3r)-9,10-dihydroxy-7-methoxy-3-methyl-3,4-dihydro-1h-benzo[g]isochromen-1-one;Semivioxanthin;

Chemical Property of semivioxanthin

Chemical Property:

• Vapor Pressure: 1.77E-10mmHg at 25°C
• Melting Point: 174-177℃
• Boiling Point: 496.4°Cat760mmHg
• PKA: 4.88±0.40(Predicted)
• Flash Point: 190.5°C
• PSA: 75.99000
• Density: 1.379g/cm³
• LogP: 2.36100

Purity/Quality:

98% ^*data from raw suppliers

(R)-Semivioxanthin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-Semivioxanthin is a naphthopyranone metabolite from the fungus Paecilomyces variotii.

Technology Process of semivioxanthin

There total 19 articles about semivioxanthin 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: 82.0%

3,4-dihydro-10-hydroxy-7-methoxy-9-methoxymethoxy-3-methyl-1-oxo-1H-naphtho<2,3-c>pyran (153413-94-6) → Semivioxanthin (70477-26-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1080/00397919308011118

Reference yield: 66.0%

(R)-3,4-dihydro-10-hydroxy-7-methoxy-9-(2-methoxyethoxy)methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one (1160957-74-3) → (+)-semivioxanthin (70477-26-8)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2009.03.016

Reference yield: 51.0%

1,8-Dihydroxy-6-methoxy-3-(2-oxo-propyl)-naphthalene-2-carboxylic acid methyl ester (127983-39-5) → Semivioxanthin (70477-26-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -78 ℃; for 1h;

upstream raw materials:

(R)-9-benzyloxymethoxy-3,4-dihydro-10-hydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one

2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester

methyl 2-benzyloxymethoxy-4-methoxy-6-methylbenzoate

(R)-3,4-dihydro-10-hydroxy-7-methoxy-9-(2-methoxyethoxy)methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one

Refernces

• 1、 Tan, Nichole P.H.,Donner, Christopher D.. "Total synthesis and confirmation of the absolute stereochemistry of semiviriditoxin, a naphthopyranone metabolite from the fungus Paecilomyces variotii". experimental part. p. 4007 - 4012. Retrieved 2009/09/30.
• 2、 Deshpande,Khan,Rai,Ayyangar. "Synthesis of semivioxanthin". . p. 2337 - 2345. Retrieved 2007/10/02.