68711-40-0

Basic information

• Product Name: (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone
• Synonyms: (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone;(3S,4S)-3-Hexyl-4-[(2S)-2-hydroxytridecyl]-2-oxetanone;(3S,4S)-3-Hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one;[3S-[3α,4β(R*)]]-3-Hexyl-4-(2-hydroxytridecyl)-2-oxetanone
• CAS NO: 68711-40-0
• Molecular Formula: C₂₂H₄₂O₃
• Molecular Weight: 354.57
• Product Categories: Chiral Reagents;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68711-40-0.mol
• Article Data: 48

Chemical Properties

• Melting Point: 63-64 °C
• Boiling Point: 467.893 °C at 760 mmHg
• Flash Point: 176.152 °C
• Appearance: /
• Density: 0.935g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.71±0.20(Predicted)
• CAS DataBase Reference: (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone(68711-40-0)
• EPA Substance Registry System: (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone(68711-40-0)

Safety Data

• Hazardous Substances Data: 68711-40-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(3S,4S)-3-Hexyl-4-[(2S)-2-hydroxytridecyl]-2-oxetanone is an analog of Tetrahydrolipstatin, an inhibitor of the hydrolysis of endocannabinoid 2-arachidonoylglycerol (2-AG), also an intermediate in the preparation of Orlistat (O686500).

InChI:InChI=1/C22H42O3/c1-3-5-7-9-10-11-12-13-14-16-19(23)18-21-20(22(24)25-21)17-15-8-6-4-2/h19-21,23H,3-18H2,1-2H3/t19?,20-,21?/m0/s1

Upstream product

• 1072902-83-0 (2S,3S,5S)-2-hexyl-3-hydroxy-5-((triisopropylsilyl)oxy)hexadecanoic acid 
• 244628-38-4 (3S,4S,2'R,1Z)-3-(1-hexenyl)-4-(2'-phenylmethyloxy-tridecyl)-2-oxetanone 
• 112763-97-0 (R)-3-phenylmethyloxy-tetradecanal 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 104801-96-9 (3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one 
• 124-07-2 Octanoic acid 
• 214683-66-6 ({(E)-(S)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-heptyl]-tetradec-2-enyl}-dimethyl-silanyl)-benzene 
• 214683-65-5 (E)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid tert-butyl ester 
• 214683-79-1 (Z)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid tert-butyl ester 
• 638-45-9 1-Iodohexane 
• 130645-87-3 (7R,8S,10S)-10-Benzyloxy-7-(tert-butyldimethylsilyloxymethyl)-8-dimethyl(phenyl)silylhenicosane 
• 130625-79-5 (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid 
• 130625-76-2 (Z)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid benzyl ester 
• 130625-78-4 (7R,8S,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-8-(dimethyl-phenyl-silanyl)-henicosan-10-ol 

Downstream Products

• 68711-41-1 (S,E)-Henicos-7-en-10-ol 
• 104872-04-0 Orlistat 
• 112764-05-3 (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester 
• 104801-96-9 (3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one 
• 108051-94-1 N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 1225451-00-2 (R)-1'-<((2''S,3''S)-3''-hexyl-4''-oxo-2''-oxetanyl)methyl>dodecyl (S)-N-formylleucinate 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 
• 112764-01-9 (3S,4S,6R)-4-(benzyloxy)-3-hexyl-3,4,5,6-tetrahydro-6-undecyl-2H-pyran-2-one 
• 112764-03-1 benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-hydroxyhexadecanoate 
• 1072902-86-3 N-[(phenylmethoxy)carbonyl]-β-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 1072902-85-2 N-[(phenylmethoxy)carbonyl]-L-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 1072902-87-4 N-[(phenylmethoxy)carbonyl]-L-valine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 1072902-69-2 N-[(phenylmethoxy)carbonyl]-D-leucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 1072902-79-4 N-[(phenylmethoxy)carbonyl]-L-phenylalanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 

Relevant articles and documents

One-step modification to identify dual-inhibitors targeting both pancreatic triglyceride lipase and Niemann-Pick C1-like 1

Pancreatic triglyceride lipase (PTL) and Niemann-Pick C1-like 1 (NPC1L1) have been identified as attractive therapeutic targets for obesity and hypercholesteremia, respectively. Obesity and hypercholesteremia usually co-exist, however no dual-inhibitors against PTL and NPC1L1 were reported for the treatment of obesity patients with hypercholesteremia so far. In this work, molecular hybridization-based one-step modification screening identified a potent dual-inhibitor against PTL and NPC1L1. Compound P1-11 has IC50 values of 2.1 μM against PTL through covalent binding, as well as significantly reduces cholesterol absorption in a non-competitive inhibitory manner. Molecule docking and molecular dynamics studies revealed the reason of its activity to both PTL and NPC1L1. Moreover, the gene and protein expression levels of PTL and NPC1L1 were also determined respectively after the treatment of P1-11. Development of dual-inhibitors against PTL and NPC1L1 could provide novel treatment options for obesity patients with hypercholesteremia. The results of current research would great support the development of dual-inhibitors against PTL and NPC1L1.

Refining method for key intermediate of orlistat

The invention discloses a refining method for a key intermediate of orlistat as well as key intermediate impurities and a preparation method thereof. The refining method comprises the step that a compound I is recrystallized in an organic solvent or a mixed organic solvent to remove impurities 1-5 which are difficult to remove in a process. The method has good selectivity on the impurities 1-5, and is simple and convenient to operate, low in cost and suitable for industrial production. The invention also provides an impurity 3 and a preparation method thereof, and application of the impurity 3 as an impurity reference substance of an orlistat key intermediate (3S,4S)-3-hexyl-4-[(R)-2-(hydroxytridecyl)]oxetan-2-one (the compound I).

COMPOUNDS FOR THE REDUCING LIPOTOXIC DAMAGE

Provided herein are novel lipase inhibitors and methods for using the same to treat inflammation, multisystem organ failure, necrotic pancreatic acinar cell death, acute pancreatitis, sepsis (e.g., culture negative sepsis), burns, and acne. For example, provided herein are two novel lipase inhibitors useful in the methods described herein: (I) (II) or a pharmaceutically acceptable salt thereof.