4-Methoxy Retinoic Acid Methyl Ester

Base Information

• Chemical Name: 4-Methoxy Retinoic Acid Methyl Ester
• CAS No.: 163808-81-9
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• DSSTox Substance ID: DTXSID90439789
• Mol file: 163808-81-9.mol

Synonyms:4-Methoxy Retinoic Acid Methyl Ester;163808-81-9;methyl (2E,4E,6E,8E)-9-(3-methoxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoate;METHYL (2E,4E,6E,8E)-9-(3-METHOXY-2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)-3,7-DIMETHYLNONA-2,4,6,8-TETRAENOATE;starbld0001201;DTXSID90439789

Chemical Property of 4-Methoxy Retinoic Acid Methyl Ester

Chemical Property:

• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform, Dichloromethane, Ehtyl Acetate
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 628

Purity/Quality:

95% ^*data from raw suppliers

4-MethoxyRetinoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(CCC1OC)(C)C)C=CC(=CC=CC(=CC(=O)OC)C)C
• Isomeric SMILES: CC1=C(C(CCC1OC)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)OC)/C)/C
• Uses: all-trans Retinoic Acid (R250200) impurity.

Technology Process of 4-Methoxy Retinoic Acid Methyl Ester

There total 6 articles about 4-Methoxy Retinoic Acid Methyl Ester 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: 12.0%

all-trans-methyl retinoate (339-16-2) → methyl 5-acetyl-4,18-dinor-retinoate + methyl 4-methoxyretinoate (163808-81-9) + (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester (163955-59-7)

Guidance literature:

With trifluoroacetic acid; lithium chloride; In methanol; at 23 ℃; for 240h;

DOI:10.1248/cpb.43.356

Reference yield: 12.0%

methanol (67-56-1) + all-trans-methyl retinoate (339-16-2) → methyl 5-acetyl-4,18-dinor-retinoate + methyl 4-methoxyretinoate (163808-81-9) + (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester (163955-59-7)

Guidance literature:

With trifluoroacetic acid; lithium chloride; at 23 ℃; for 240h;

DOI:10.1248/cpb.43.356

Reference yield:

4-Hydroxyretinoic acid methyl ester (38030-59-0) + methyl iodide (74-88-4) → (13E)-3,7-dimethyl-9-[(3RS)-3-methoxy-2,6,6-trimethylcyclohexenyl]-2,4,6,8-nontetraenoate methyl ester (163808-81-9)

Guidance literature:

4-Hydroxyretinoic acid methyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 10 - 20 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 10 - 20 ℃; for 2h;

upstream raw materials:

methanol

all-trans-methyl retinoate

all-trans-retinoic-acid

4-Oxo-retinoic acid methyl ester

Downstream raw materials:

4-methoxyretinoic acid