5,7-Dimethoxyflavanone

Base Information

• Chemical Name: 5,7-Dimethoxyflavanone
• CAS No.: 1036-72-2
• Molecular Formula: C17H16 O4
• Molecular Weight: 284.312
• Hs Code.: 2932999099
• NSC Number: 661206
• DSSTox Substance ID: DTXSID20908493
• Nikkaji Number: J109.876D
• Wikidata: Q27189587
• Metabolomics Workbench ID: 27381
• ChEMBL ID: CHEMBL107131
• Mol file: 1036-72-2.mol

Synonyms:5,7-Dimethoxyflavanone;1036-72-2;5,7-dimethoxy-2-phenylchroman-4-one;5,7-Dimethoxyflavanon;Dimethylpinocembrin;Flavanone, 5,7-dimethoxy-;NSC661206;5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one;alpinetin methyl ether;5,7-Dimethoxy-2-phenyl-chroman-4-one;5,7-Dimethoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one;CHEMBL107131;Pinocembrin 5,7-dimethyl ether;36052-66-1;NSC 661206;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-phenyl-;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-phenyl-, (2S)-;5,7-Dimethoxyflavonone;Spectrum_000324;SpecPlus_000873;5,7-Dimethoxylflavanone;Spectrum2_001357;Spectrum3_000587;Spectrum4_001873;Spectrum5_000466;BSPBio_002034;KBioGR_002369;KBioSS_000804;DivK1c_006969;SPBio_001573;(2R)-2,3-Dihydro-5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one;MEGxp0_000558;SCHEMBL2879027;ACon1_001227;KBio1_001913;KBio2_000804;KBio2_003372;KBio2_005940;KBio3_001534;DTXSID20908493;CHEBI:110206;BDBM50338969;CCG-38839;HY-N10879;LMPK12140217;MFCD00143414;NSC-661206;NCGC00142553-01;NCGC00142553-02;NCGC00142553-03;NCI60_021335;CS-0637334;FT-0619849;FT-0775382;SR-05000002541;SR-05000002541-1;BRD-A90249268-001-03-2;BRD-A90249268-001-04-0;Q27189587;5,7-Dimethoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one #;B0005-053969;5,7-Dimethoxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one;5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Chemical Property of 5,7-Dimethoxyflavanone

Chemical Property:

• Vapor Pressure: 5.79E-09mmHg at 25°C
• Melting Point: 144-146°C
• Boiling Point: 468.8°Cat760mmHg
• Flash Point: 209.4°C
• PSA: 44.76000
• Density: 1.204g/cm³
• LogP: 3.41030
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 284.10485899
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,7-Dimethoxyflavanone ≥98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C(=O)CC(O2)C3=CC=CC=C3)C(=C1)OC

Technology Process of 5,7-Dimethoxyflavanone

There total 41 articles about 5,7-Dimethoxyflavanone 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: 93.0%

5,7-dimethoxy-4H-chromen-4-one (59887-91-1) + phenylboronic acid (98-80-6) → Pinocembrin dimethyl ether (1036-72-2,36052-66-1,89395-30-2)

Guidance literature:

With [Rh(OH)(cod)]2; (S)-MeO-F₁₂-BIPHEP; In water; toluene; at 60 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol2004148

Reference yield: 88.0%

(R)-3-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropan-1-one (862254-91-9) → Pinocembrin dimethyl ether (1036-72-2,36052-66-1,89395-30-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)00567-6

Reference yield: 84.0%

flavokawain B (1775-97-9) → 5,7-dimethoxyflavone (1036-72-2)

Guidance literature:

With pyridine; In methanol; water; for 12h; Heating;

upstream raw materials:

dimethyl sulfate

(R)-3-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropan-1-one

3,5-dimethoxyphenol

ethyl (R)-3-hydroxy-3-phenylpropanoate

Downstream raw materials:

8-iodo-5,7-dimethoxy-2-phenyl-chroman-4-one

pinostrobin

3-iodo-5,7-dimethoxy-2-phenyl-chroman-4-one

pinostrobin

Refernces

• 1、 Kshatriya,Machhi,Nazeruddin. "Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions". . p. 857 - 862. Retrieved 2014.
• 2、 Pandey, G.,Krishna, A.,Kumaraswamy, G.. "PHOTOSENSITIZED (SET) CONVERSION OF 2'-HYDROXYCHALCONES TO FLAVONOIDS A PROBABLE BIOGENETIC PATHWAY". . p. 4615 - 4616. Retrieved 1987.
• 3、 Kong, Wenlong,Lai, Jixing,Li, Shengkun,Yang, Juan. "Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads". . . Retrieved 2022/03/31.
• 4、 Kasashima, Yoshio,Mino, Takashi,Sakamoto, Masami,Shimizu, Waku,Uemura, Naohiro,Yoshida, Yasushi. "Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors". . p. 5676 - 5681. Retrieved 2020/10/13.