(2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid

Base Information

• Chemical Name: (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid
• CAS No.: 130793-30-5
• Molecular Formula: C22H44O4
• Molecular Weight: 372.589
• Mol file: 130793-30-5.mol

Synonyms:(2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid ;[2S-(2R*,3R*,5R*)]-;Orlistat IMpurity M3;(2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid (See H295855, SodiuM Salt)

Chemical Property of (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 61-63°C
• Boiling Point: 526.706°C at 760 mmHg
• Flash Point: 286.419°C
• PSA: 77.76000
• Density: 0.974g/cm³
• LogP: 5.69040
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform, Methanol

Purity/Quality:

95% ^*data from raw suppliers

ORLISTAT M3 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Orlistat (O686500) impurity M3.

Technology Process of (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid

There total 3 articles about (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic 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:

Orlistat (104872-04-0,104872-27-7,104872-28-8,111466-61-6,111466-62-7,111466-63-8,130193-40-7,130193-41-8,130193-42-9,130193-43-0,96829-58-2,1225451-00-2) → (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid (130793-30-5)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2021.113358

Reference yield:

(3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one (68711-33-1) → (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid (130793-30-5)

Guidance literature:

With hydrogenchloride; potassium hydroxide; In 1,4-dioxane; 1.) 1h, RT;

DOI:10.1002/hlca.19900730427

Reference yield:

Tetrahydrolipstatin (96829-58-2,104872-04-0,104872-27-7,104872-28-8,111466-61-6,111466-62-7,111466-63-8,130193-40-7,130193-41-8,130193-42-9,130193-43-0,1225451-00-2) → (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid (130793-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / 1N KOH / dioxane / 4 h / Ambient temperature

2: 1.) 1N KOH; 2.) 1N HCl / dioxane / 1.) 1h, RT

With hydrogenchloride; potassium hydroxide; In 1,4-dioxane;

DOI:10.1002/hlca.19900730427

upstream raw materials:

(3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Tetrahydrolipstatin

Orlistat

Downstream raw materials:

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

(3S,4S)-3-hexyl-4-[(2S)-2-[(triisopropylsilyl)oxy]tridecyl]oxetan-2-one

Refernces

• 1、 Stalder,Schneider,Oesterhelt. "Tetrahydrolipstatin: Thermal and hydrolytic degradation". . p. 1022 - 1036. Retrieved 2007/10/02.