Frescolat

Base Information

• Chemical Name: Frescolat
• CAS No.: 59259-38-0
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.332
• Hs Code.: 29181100
• European Community (EC) Number: 261-678-3
• UNII: XFS8QYW6WY
• DSSTox Substance ID: DTXSID601315646
• Nikkaji Number: J2.067.184J
• RXCUI: 1866625
• Mol file: 59259-38-0.mol

Synonyms:l-menthyl lactate

Chemical Property of Frescolat

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 8.58E-05mmHg at 25°C
• Melting Point: 40 °C
• Refractive Index: -80 ° (C=5, MeOH)
• Boiling Point: 304 °C at 760 mmHg
• PKA: 13.01±0.20(Predicted)
• Flash Point: 116 °C
• PSA: 46.53000
• Density: 0.99 g/cm³
• LogP: 2.37120
• Storage Temp.: 2-8°C
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 228.17254462
• Heavy Atom Count: 16
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

L-Menthyl lactate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 24/25-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C(C)O)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@@H](C)O)C(C)C
• Description: L-Menthyl lactate has a weak odor somewhat reminiscent of tobacco and chamomile. It is almost tasteless, with a lasting gentle cooling effect.
• Uses: L-Menthyl Lactate is used in preparation of amides for generating a trigeminal sensory effect.

Technology Process of Frescolat

There total 3 articles about Frescolat 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:

2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (951-98-4) → (-)-menthyl lactate (17162-29-7,61597-98-6,59259-38-0,185915-25-7)

Guidance literature:

With 1-naphthylphenylsilane; Rh catalyst; In benzene;

DOI:10.1021/jo00430a001

Reference yield:

2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (951-98-4) → (1R,2S,5R)-menthyl (S)-(-)-lactate (61597-98-6,185915-25-7) + (-)-menthyl lactate (17162-29-7,61597-98-6,59259-38-0,185915-25-7)

Guidance literature:

With LiAlH; In tetrahydrofuran; at -78 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)80456-5

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propionate (29066-36-2,68539-56-0,86014-82-6,109716-85-0,127471-65-2,141552-99-0,141553-01-7,4951-48-8) → (1R,2S,5R)-menthyl (S)-(-)-lactate (61597-98-6,185915-25-7) + (-)-menthyl lactate (17162-29-7,61597-98-6,59259-38-0,185915-25-7)

Guidance literature:

With MoO₅*pyridine*HMPA; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, 2.) THF, hexane;

DOI:10.1016/S0957-4166(00)86253-9

upstream raw materials:

2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propionate

Downstream raw materials:

(R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate

Refernces

• 1、 Boireau, G.,Deberly, A.. "Highly diastereoselective reduction of (-) menthylphenylglyoxalate and (-) menthylpyruvate using new hindered lithiumtrialkoxyaluminohydrides". . p. 771 - 774. Retrieved 2007/10/02.