(3R)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Base Information

• Chemical Name: (3R)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one
• CAS No.: 480-33-1
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.188
• UNII: Y30Y67M5SV
• Nikkaji Number: J12.353F
• Wikipedia: Mellein
• Wikidata: Q104399016
• Metabolomics Workbench ID: 139391
• ChEMBL ID: CHEMBL499303
• Mol file: 480-33-1.mol

Synonyms:mellein;ochracin

Chemical Property of (3R)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Chemical Property:

• Vapor Pressure: 9.9E-07mmHg at 25°C
• Boiling Point: 392.7oC at 760 mmHg
• Flash Point: 181.3oC
• PSA: 46.53000
• Density: 1.252g/cm3
• LogP: 1.49360
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 214

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-(-)-Mellein ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=C(C(=CC=C2)O)C(=O)O1
• Isomeric SMILES: C[C@@H]1CC2=C(C(=CC=C2)O)C(=O)O1
• Uses: (R)-(?)-Mellein is a dihydroisocoumarin compound produced by A. ochraceus Wilhelm. It has a variety of biological activities including antibacterial, antimalarial, antifungal, and anticancer effects. (R)-(?)-Mellein inhibits proliferation of human breast cancer (MCF-7 and MDA-MB-468) and melanoma (SK-MEL-28 and Malme-3M) cell lines with IC50 values greater than 200 μM.[Cayman Chemical]

Technology Process of (3R)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

There total 32 articles about (3R)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one 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: 98.0%

8-hydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-isochromen-1-one (126784-47-2) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2006.11.068

Reference yield: 97.0%

8-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one (16281-42-8,30407-92-2,76985-75-6) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With hydrogen bromide; acetic acid; for 4h; Heating;

DOI:10.1016/S0957-4166(97)00217-6

Reference yield: 97.0%

(R)-(-)-mellein acetate (104331-43-3) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With methanol; water; triethylamine; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96780-8

upstream raw materials:

carbon dioxide

(R)-1-(3-Methoxymethoxy-phenyl)-propan-2-ol

1-Methoxymethoxy-3-((R)-2-methoxymethoxy-propyl)-benzene

(-)-3,4-dihydro-8-hydroxy-3-methyl-7-isocoumarincarboxylic acid

Downstream raw materials:

2-hydroxy-6-methylbenzoic acid

6-(1-propenyl)salicylic acid

(1R,3S)-(-)-thysanone

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