Methyl mycophenolate

Base Information

• Chemical Name: Methyl mycophenolate
• CAS No.: 31858-66-9
• Molecular Formula: C18H22 O6
• Molecular Weight: 334.369
• UNII: 0B5C0EG8E8
• DSSTox Substance ID: DTXSID501112946
• Nikkaji Number: J2.135.783I
• Wikidata: Q27236563
• ChEMBL ID: CHEMBL237760
• Mol file: 31858-66-9.mol

Synonyms:Methyl mycophenolate;31858-66-9;Methyl Mycophenolate (EP Impurity E);Mycophenolic Acid Methyl Ester;(E/Z)-Methyl mycophenolate;24243-40-1;UNII-0B5C0EG8E8;methyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate;0B5C0EG8E8;CHEMBL237760;4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, methyl ester, (4E)-;Mycophenolate mofetil specified impurity E [EP];Methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate;methyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate;Mycophenolate mofetil impurity, methyl mycophenolate- [USP];MPA-OMe;Mycophenolate methyl ester;SCHEMBL1152477;ZPXRQFLATDNYSS-BJMVGYQFSA-N;DTXSID501112946;6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enoic acid methyl ester;Mycophenolate Mofetil EP Impurity E;BDBM50331100;AKOS040744287;AT27356;HY-113972A;Mycophenolic acid methyl ester_130118;CS-0112357;J-018555;MYCOPHENOLATE MOFETIL IMPURITY E [EP IMPURITY];MYCOPHENOLATE SODIUM IMPURITY C [EP IMPURITY];Q27236563;MYCOPHENOLATE MOFETIL IMPURITY, METHYL MYCOPHENOLATE- [USP IMPURITY];(E)-Methyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate;4-Methyl-5-methoxy-6-[(E)-3-methyl-6-oxo-6-methoxy-2-hexenyl]-7-hydroxy-1,3-dihydroisobenzofuran-1-one;Methyl (4E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate;methyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate;methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7- methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate;methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -4-methyl-4-hexenoate;methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate;methyl (E)-6-(1,3-dihydro4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate;methyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-hex-4-enoate

Chemical Property of Methyl mycophenolate

Chemical Property:

• Vapor Pressure: 2.72E-12mmHg at 25°C
• Melting Point: 105-106°C
• Refractive Index: 1.556
• Boiling Point: 540.4°C at 760 mmHg
• PKA: 9.87±0.20(Predicted)
• Flash Point: 194.1°C
• PSA: 0.00000
• Density: 1.222g/cm³
• LogP: 0.45030
• Storage Temp.: -20°C Freezer
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 334.14163842
• Heavy Atom Count: 24
• Complexity: 500

Purity/Quality:

99.90% ^*data from raw suppliers

MethylMycophenolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OC)O
• Isomeric SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)OC)O
• Uses: Degradation product of Mycophenolate mofetil. EP Impurity E

Technology Process of Methyl mycophenolate

There total 27 articles about Methyl mycophenolate 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: 100.0%

methanol (67-56-1) + mycophenolic acid (24280-93-1) → methyl mycophenolate (31858-66-9)

Guidance literature:

With sulfuric acid; for 2h; Heating;

DOI:10.1002/jlcr.2580360508

Reference yield: 88.0%

(E)-6-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxymethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid methyl ester (188291-78-3) → methyl mycophenolate (31858-66-9)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; methanol; for 0.75h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00061-6

Reference yield: 86.0%

5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide (60435-90-7) → methyl mycophenolate (31858-66-9)

Guidance literature:

With boron trichloride; In dichloromethane; for 192h;

DOI:10.1016/S0040-4039(98)00423-7

upstream raw materials:

methanol

mycophenolic acid

(E)-6-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxymethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid methyl ester

5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide

Downstream raw materials:

methyl (E) 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

2-morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate hydrochloride

methyl mycophenolate 7-O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranose

mycophenolate mofetil

Refernces

• 1、 Silalai, Patamawadee,Pruksakorn, Dumnoensun,Chairoungdua, Arthit,Suksen, Kanoknetr,Saeeng, Rungnapha. "Synthesis of propargylamine mycophenolate analogues and their selective cytotoxic activity towards neuroblastoma SH-SY5Y cell line". . . Retrieved 2021.
• 2、 Smith,Waltos,Loughhead,Weikert,Morgans Jr.,Rohloff,Link,Zhu. "Asymmetric synthesis and stereochemical assignment of RS-97613, a potent immunosuppressive and antiinflammatory agent". . p. 2236 - 2241. Retrieved 1996.
• 3、 -. "LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS". Paragraph 00594. . Retrieved 2019/03/17.