Kawain

Base Information

• Chemical Name: Kawain
• CAS No.: 500-64-1
• Deprecated CAS: 40610-16-0
• Molecular Formula: C14H14 O3
• Molecular Weight: 230.263
• Hs Code.: 2932999099
• European Community (EC) Number: 207-907-2,626-921-3
• UNII: 5L1NI60TGB
• DSSTox Substance ID: DTXSID00904756
• Nikkaji Number: J1.892.684I,J2.647.246F
• Wikipedia: Kavain
• Wikidata: Q27262508
• Metabolomics Workbench ID: 144273
• ChEMBL ID: CHEMBL1482039
• Mol file: 500-64-1.mol

Synonyms:cavain;kavain;kavain, (+-)-isomer;kavain, (E)-(+-)-isomer;kavain, (R)-(E)-isomer;kavain, (R)-isomer;kavaine;kawain;Neuronica;Neuronika

Chemical Property of Kawain

Chemical Property:

• Appearance/Colour: white, fine powder
• Vapor Pressure: 1.09E-07mmHg at 25°C
• Melting Point: 142-148℃
• Refractive Index: 1.5557 (estimate)
• Boiling Point: 432.6 °C at 760 mmHg
• Flash Point: 184.6 °C
• PSA: 35.53000
• Density: 1.15 g/cm³
• LogP: 2.54560
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 324

Purity/Quality:

more than 98% ^*data from raw suppliers

Kawain ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

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: Kawain is a plant extract that shows antioxidant activity through cyclooxygenase enzyme inhibition. May also be active in tumor suppression and apoptotic induction.
• Therapeutic Function: Anesthetic; Tranquilizer

Technology Process of Kawain

There total 33 articles about Kawain 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: 87.0%

dimethyl sulfate (77-78-1) + ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (735287-46-4) → Kavain (500-64-1)

Guidance literature:

ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate; With potassium carbonate; In methanol; at 20 ℃; for 2h;

dimethyl sulfate; In acetone; at 20 ℃;

DOI:10.1021/ol0493960

Reference yield: 84.0%

(E)-3-phenylpropenal (14371-10-9) + ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane (90857-62-8) → kawain (500-64-1,1635-33-2,3155-48-4,19902-88-6,40610-16-0,86851-85-6)

Guidance literature:

With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(01)90181-9

Reference yield: 81.0%

(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester (356793-34-5) + dimethyl sulfate (77-78-1) → Kavain (500-64-1)

Guidance literature:

(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester; With potassium carbonate; In methanol; at 20 ℃; for 5h;

dimethyl sulfate; In acetone; at 20 ℃; for 12h;

DOI:10.1055/s-2005-871953

upstream raw materials:

(E)-3-phenylpropenal

((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane

ethyl γ-bromo-β-methoxy-cis-crotonate

3-phenyl-propenal

Downstream raw materials:

7,8-dihydrokavain

5,6-dehydrokawain

7,8-dihydrokawain

5-((E)-2-Hydroxy-4-phenyl-but-3-enyl)-1,2-dihydro-pyrazol-3-one

Refernces

• 1、 Akagawa, Kengo,Kudo, Kazuaki. "Biomimetic iterative method for polyketide synthesis". supporting information. p. 8645 - 8648. Retrieved 2017/08/10.
• 2、 Mineno, Masahiro,Sawai, Yasuhiro,Kanno, Kazuaki,Sawada, Naotaka,Mizufune, Hideya. "A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2- pyrones through double Reformatsky reaction". . p. 10921 - 10926. Retrieved 2014/01/06.