Demethoxyyangonin

Base Information

• Chemical Name: Demethoxyyangonin
• CAS No.: 15345-89-8
• Deprecated CAS: 26531-51-1
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.247
• UNII: F2MBQ8QRUN
• ChEMBL ID: CHEMBL254218
• DSSTox Substance ID: DTXSID4033390
• Metabolomics Workbench ID: 46463
• Nikkaji Number: J13.042G,J81.846A
• NSC Number: 112161,68686
• Wikidata: Q5264611
• Wikipedia: Desmethoxyyangonin
• Mol file: 15345-89-8.mol

Synonyms:Desmethoxyyangonin;5,6-Dehydrokawain;Demethoxyyangonin;15345-89-8;Desmethoxy Yangonin;5,6-Dehydrokavain;(E)-4-Methoxy-6-styryl-2H-pyran-2-one;1952-41-6;Yangonin, demethoxy-;4-Methoxy-6-styryl-2H-pyran-2-one;NSC 112161;F2MBQ8QRUN;UNII-F2MBQ8QRUN;2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-phenylethenyl]-;4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one;2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)-;CCRIS 9369;DTXSID4033390;(E)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one;NSC 68686;NSC-68686;2H-Pyran-2-one, 4-methoxy-6-styryl-, (E)-;NSC-112161;CHEBI:1995;DMY;DTXCID2013390;4-methoxy-6-[(E)-styryl]pyran-2-one;5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one;26531-51-1;4-methoxy-6-[(E)-2-phenylvinyl]-2H-pyran-2-one;4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one;4-methoxy-6-(2-phenylethenyl)-2h-pyran-2-one;2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-PHENYLETHENYL)-;trans-5,6-Dehydrokawain;5,6-Dehydrokawin;SCHEMBL236641;4-Methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one;CHEMBL254218;DKKJNZYHGRUXBS-BQYQJAHWSA-N;2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI);HY-N0918;NSC68686;Tox21_200296;MFCD00221730;NSC112161;AKOS015896811;Desmethoxyyangonin, analytical standard;CCG-208562;CS-4242;NCGC00091904-01;NCGC00091904-02;NCGC00257850-01;AC-34590;AS-68696;4-Methoxy-6-styryl-(E)-2H-Pyran-2-one;CAS-15345-89-8;C09925;A809430;SR-05000002195;2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-;Q5264611;SR-05000002195-2;4-Methoxy-6-(2-phenylethenyl)-(E)-2H-Pyran-2-one;2H-Pyran-2-one, 4-methoxy-6-[(E)-2-phenylethenyl]-

Chemical Property of Demethoxyyangonin

Chemical Property:

• Appearance/Colour: white to faint yellow powder
• Vapor Pressure: 6.09E-08mmHg at 25°C
• Melting Point: 138-140 ºC
• Boiling Point: 440 °C at 760 mmHg
• Flash Point: 188 °C
• PSA: 39.44000
• Density: 1.18 g/cm³
• LogP: 2.81880
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.078644241
• Heavy Atom Count: 17
• Complexity: 371

Purity/Quality:

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

Demethoxyyangonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
• Isomeric SMILES: COC1=CC(=O)OC(=C1)/C=C/C2=CC=CC=C2
• Uses: The microsomal metabolite The microsomal metabolite of Yangonin (Y100550).

Technology Process of Demethoxyyangonin

There total 22 articles about Demethoxyyangonin 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: 95.0%

4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one (2082-94-2) + dimethyl sulfate (77-78-1) → 5,6-dehydrokawain (1952-41-6,15345-89-8,23768-64-1,26531-51-1)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Reflux; Inert atmosphere;

DOI:10.1080/00397911.2018.1455212

Reference yield: 91.0%

kawain (500-64-1,1635-33-2,3155-48-4,19902-88-6,40610-16-0,86851-85-6) → 5,6-dehydrokawain (1952-41-6,15345-89-8,23768-64-1,26531-51-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 4h; Heating;

DOI:10.1002/jhet.5570180227

Reference yield: 51.0%

benzaldehyde (100-52-7) + 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one (77037-53-7) → 5,6-dehydrokawain (1952-41-6,15345-89-8,23768-64-1,26531-51-1)

Guidance literature:

4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one; With lithium diisopropyl amide; In tetrahydrofuran; at -120 ℃;

benzaldehyde; In tetrahydrofuran; at -120 - 20 ℃; for 3h;

With sulfuric acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1071/ch99119

upstream raw materials:

diazomethane

6-trans-styryl-pyran-2,4-dione

dimethyl sulfate

kawain

Downstream raw materials:

7,8-dihydrokawain

4-acetoxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one

4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one

Refernces

• 1、 Li, Chanjuan,Cheng, Bao,Fang, Sai,Zhou, Huihao,Gu, Qiong,Xu, Jun. "Design, syntheses and lipid accumulation inhibitory activities of novel resveratrol mimics". . p. 114 - 122. Retrieved 2018.
• 2、 Obi, Grace,Van Heerden, Fanie R.. "Synthesis of 5,6-dehydrokawain and some fluorinated analogues". . p. 1482 - 1486. Retrieved 2018/05/31.