4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-
• CAS No.: 206660-42-6
• Molecular Formula: C15H12O4
• Molecular Weight: 256.258
• DSSTox Substance ID: DTXSID30349853
• Wikidata: Q63395297
• Metabolomics Workbench ID: 133528
• ChEMBL ID: CHEMBL399249
• Mol file: 206660-42-6.mol

Synonyms:206660-42-6;(R)-PINOCEMBRIN;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-;(2R)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one;(R)-5,7-Dihydroxy-2-phenylchroman-4-one;(2R)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one;pinocembrine;(2R)-5,7-dihydroxy-2-phenylchroman-4-one;(R)-5,7-dihydroxyflavanone;CHEMBL399249;SCHEMBL10080882;BDBM26666;DTXSID30349853;URFCJEUYXNAHFI-CYBMUJFWSA-N;TNP00071;AKOS030254805;NCGC00017205-01;NCGC00017205-02;NCGC00142377-01;(2R)-5,7-dihydroxy-2-phenyl-chroman-4-one;A14759;A836234;Q63395297

Chemical Property of 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-

Chemical Property:

• Melting Point: 195-198°C
• PSA: 66.76000
• LogP: 2.80430
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

(R)-Pinocembrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• Isomeric SMILES: C1[C@@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• Uses: (2R)-Pinocembrin is the (R)-enantiomer of Pinocembrin, a flavanoid with antioxidant activity found in damiana, honey, and propolis. (2R)-Pinocembrin is a potential inhibitor of PIM1 kinase, an oncogen e that has been implicated in the development of leukemias, lymphomas, and prostate cancer. (2R)-Pinocembrin is the (R)-enantiomer of Pinocembrin, a flavanoid with antioxidant activity found in damiana, honey, and propolis. (2R)-Pinocembrin is a potential inhibitor of PIM1 kinase, an oncogene that has been implicated in the development of leukemias, lymphomas, and prostate cancer.

Technology Process of 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-

There total 8 articles about 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)- 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: 90.0%

C22H18O4 (1159852-74-0) → (R)-5,7-dihydroxyflavanone (206660-42-6)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In water; N,N-dimethyl-formamide; for 5h; under 760.051 Torr;

Reference yield: 90.0%

C21H16O4 → (R)-5,7-dihydroxyflavanone (206660-42-6)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In water; N,N-dimethyl-formamide; under 760.051 Torr;

Reference yield:

pinocembrin (480-39-7,61490-55-9,68745-38-0) → (R)-5,7-dihydroxyflavanone (206660-42-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate; potassium iodide / ethyl acetate / 2 h / Reflux

2: titanium tetrachloride; triethylamine / benzene / 48 h / Inert atmosphere

3: water; hydrogenchloride / ethanol / 1.5 h / Reflux

4: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide

With hydrogenchloride; palladium 10% on activated carbon; water; hydrogen; titanium tetrachloride; potassium carbonate; triethylamine; potassium iodide; In ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/acs.jnatprod.6b00474

upstream raw materials:

(1S)-10-camphorsulfonic acid

2'.4'.6'-triacetoxy-trans-chalcone

C₂₂H₁₈O₄

5,7-dihydroxy-2-phenyl-chromen-4-one