4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid

Base Information

• Chemical Name: 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid
• CAS No.: 77341-67-4
• Deprecated CAS: 754938-59-5
• Molecular Formula: C14H24O4
• Molecular Weight: 256.342
• Hs Code.: 2918990090
• European Community (EC) Number: 426-890-4,616-452-2
• UNII: 85MHF9Y3DI
• DSSTox Substance ID: DTXSID10228071
• Nikkaji Number: J2.067.185H
• Wikidata: Q27269657
• Mol file: 77341-67-4.mol

Synonyms:monomenthyl succinate

Chemical Property of 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 62.0 to 66.0 °C
• Refractive Index: 1.478
• Boiling Point: 259.2 °C at 760 mmHg
• PKA: 4.42±0.17(Predicted)
• Flash Point: 104.5 °C
• PSA: 63.60000
• Density: 1.21 g/cm³
• LogP: 2.85520
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 256.16745924
• Heavy Atom Count: 18
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

(-)-Menthyl Succinate >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)CCC(=O)O)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)CCC(=O)O)C(C)C

Technology Process of 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid

There total 22 articles about 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid 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: 99.9%

succinic acid anhydride (108-30-5) + (-)-menthol (2216-51-5) → L-menthylsuccinic acid (77341-67-4)

Guidance literature:

at 110 ℃; for 8h; Autoclave; Inert atmosphere; Neat (no solvent);

Reference yield: 83.0%

(-)-menthyl acrylate (4835-96-5) + cesium formate (3495-36-1) → L-menthylsuccinic acid (77341-67-4)

Guidance literature:

With bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium⁽¹⁺⁾; 2-(2-pyridyl)pyridine; hexafluorophosphate; In dimethyl sulfoxide; at 50 ℃; for 12h; Inert atmosphere; Irradiation;

DOI:10.1021/acscatal.1c04684

Reference yield:

succinic acid anhydride (108-30-5) + menthol (15356-70-4) → (1S,2R,5S)-(+)-menthol (15356-60-2) + (-)-menthol (2216-51-5) + L-menthylsuccinic acid (77341-67-4) + 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid (204326-53-4)

Guidance literature:

With Candida cylindracea lipase; In diethyl ether; at 20 ℃; for 24h; Schlenk technique; Resolution of racemate; Enzymatic reaction;

DOI:10.1007/s11164-018-3525-7

upstream raw materials:

succinic acid anhydride

(-)-menthol

Neomenthol

DL-neomenthol

Downstream raw materials:

3-p-menthene

succinic acid anhydride

menthol

N-{3-((E)-2-Allyloxycarbonyl-vinyl)-5-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyl)-propionylamino]-phenyl}-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester