6-Hydroxymellein

Base Information

• Chemical Name: 6-Hydroxymellein
• CAS No.: 19314-92-2
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Mol file: 19314-92-2.mol

Synonyms:3,4-Dihydro-6,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one

Chemical Property of 6-Hydroxymellein

Chemical Property:

• Melting Point: 209-211 °C
• Boiling Point: 472.3±34.0 °C(Predicted)
• PKA: 8.11±0.40(Predicted)
• PSA: 66.76000
• Density: 1.380±0.06 g/cm3(Predicted)
• LogP: 1.19920

Purity/Quality:

6,8-Dihydroxy-3-methylisochroman-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 6,8-Dihydroxy-3-methylisochroman-1-one is an intermediate used in the total synthesis of 6,8-dimethoxy-3-methylisocoumarin, a fungal metabolite precursor.

Technology Process of 6-Hydroxymellein

There total 15 articles about 6-Hydroxymellein 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: 88.0%

3,4-dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one (77844-97-4) → 3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-one (19314-92-2)

Guidance literature:

With boron tribromide; In dichloromethane; a.) -10 deg C, 30 min, b.) RT, 1 h;

DOI:10.1080/00397919208021540

Reference yield:

ethyl orselinate (2524-37-0) → 3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-one (19314-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / K₂CO₃ / acetone / Heating

2: 1.) LDA, 2.) acetaldehyde / 1.) THF, hexane-78 deg C, 30 min, 2.) THF, hexane, a.) -78deg C, 1 h, b.) RT, overnight

3: 88 percent / BBr₃ / CH₂Cl₂ / a.) -10 deg C, 30 min, b.) RT, 1 h

With boron tribromide; potassium carbonate; acetaldehyde; lithium diisopropyl amide; In dichloromethane; acetone;

DOI:10.1080/00397919208021540

Reference yield:

6,8‐dimethoxy‐3‐methylisocoumarin (18110-66-2) → 3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-one (19314-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / sodium borohydride / 1 h / Heating

2: 82 percent / boron tribromide / CH₂Cl₂ / 1.) -70 deg C, 24 h, 2.) -70 deg C-room temperature, 12 h

With sodium tetrahydroborate; boron tribromide; In dichloromethane;

upstream raw materials:

3,4-dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one

ethyl orselinate

ethyl 2,4-dimethoxy-6-methylbenzoate

6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione

Downstream raw materials:

6-methoxymellein

(+)-terrein

Refernces

• 1、 Kendall, J. Kirby,Fisher, Thomas H.,Schultz, Harry P.,Schultz, Tor P.. "An Improved Synthesis of 6,8-Dimethoxy-3-methylisocoumarin, a Fungal Metabolite Precursor". . p. 4218 - 4220. Retrieved 2007/10/02.
• 2、 Hill, Robert A.,Carter, Rachel H.,Staunton, James. "Biosynthesis of Fungal Metabolites. Terrein, a Metabolite of Aspergillus terreus Thom". . p. 2570 - 2576. Retrieved 2007/10/02.