Pharmakon1600-01504300

Base Information

• Chemical Name: Pharmakon1600-01504300
• CAS No.: 96829-58-2
• Molecular Formula: C₂₉H₅₃NO₅
• Molecular Weight: 495.744
• Hs Code.: 29322090
• NSC Number: 758881
• Mol file: 96829-58-2.mol

Synonyms:Spectrum_001709;Spectrum2_001678;Spectrum3_001670;Spectrum4_000637;Spectrum5_001472;BSPBio_003459;KBioGR_001254;KBioSS_002189;SPECTRUM1504300;SPBio_001895;KBio2_002189;KBio2_004757;KBio2_007325;KBio3_002679;HMS1922J19;HMS2093G10;Pharmakon1600-01504300;CCG-39096;NSC758881;NCGC00178051-01;SBI-0206793.P001;AB01563297_01;SR-05000001995;SR-05000001995-1

Chemical Property of Pharmakon1600-01504300

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 4.23E-15mmHg at 25°C
• Melting Point: <50 °C
• Refractive Index: 1.469
• Boiling Point: 615.9 °C at 760 mmHg
• PKA: 14.59±0.23(Predicted)
• Flash Point: 326.3 °C
• PSA: 81.70000
• Density: 0.976 g/cm³
• LogP: 7.90870
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 19 mg/mL
• XLogP3: 10
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 23
• Exact Mass: 495.39237379
• Heavy Atom Count: 35
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

Orlistat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=O
• Isomeric SMILES: CCCCCCCCCCC[C@@H](C[C@@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@@H](CC(C)C)NC=O
• Mechanism of Action and Pharmacological Properties: Orlistat is a reversible inhibitor of pancreatic and gastric lipase. It blocks the hydrolysis of triglycerides and reduces fat absorption by about 30%.; Approved by the FDA as an anti-obesity drug in 1999. Widely available in more than 120 countries. Demonstrated to have anti-obesity and antioxidant properties.
• Clinical Applications: Approved for long-term use to manage body weight in obese and overweight adults and adolescents.; Reduces serum total cholesterol and low-density lipoprotein cholesterol (LDL-C) levels independent of weight loss.; Used in combination with a low-calorie diet for the treatment of obesity.
• Anti-Tumor Activity: Emerging evidence suggests potential anti-tumor effects of Orlistat.; Inhibits the survival ability of hepatocellular carcinoma in mice by activating the AKT/mTOR signaling cascades.; Promotes tumor cell apoptosis through various molecular mechanisms, including inhibition of NF-魏B, caspase3/caspase9, AKT/mTOR, and TRAIL signaling pathways.; Induces apoptosis in prostate cancer cells and interferes with tumor cell cycles.
• Pharmacotherapy for Obesity in Adolescents: Orlistat is approved by the FDA for use in adolescent obesity. Results in a 30% reduction in dietary fat absorption.; One of the two medications approved for adolescent obesity by the FDA.
• Molecular Effects on Cancer Cells: Inhibitor of the thioesterase domain of FASN, interfering with cellular fatty acid synthesis. Induces apoptosis and inhibits tumor growth in various cancer cells, including breast cancer cell lines (MDA-MB-231, MDA-MB-468, and MCF-7).
• General Description: Orlistat, also known as (-)-tetrahydrolipstatin or Xenical, is a potent and irreversible inhibitor of pancreatic lipase used as an anti-obesity medication. Its biological activity stems from its γ-lactone structure with specific antistereochemistry, which effectively blocks fat absorption in the digestive system. Orlistat's synthesis involves asymmetric strategies to establish key stereocenters, including an anti-aldol reaction and diastereoselective reduction, yielding high selectivity and efficiency.

Technology Process of Pharmakon1600-01504300

There total 241 articles about Pharmakon1600-01504300 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: 95.2%

(-)-lipstatin (96829-59-3) → 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)

Guidance literature:

With sodium tetrahydroborate; (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine cobalt; copper(l) chloride; In acetonitrile; at 15 ℃; Temperature; Reagent/catalyst; Inert atmosphere;

Reference yield: 94.0%

N-formyl-L-leucine (5338-45-4,44978-39-4,89921-44-8,6113-61-7) + (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone (68711-40-0,104871-99-0,104872-00-6,104872-03-9,104872-05-1,104872-07-3,104872-19-7,104872-06-2) → 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)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/0l1002913

Reference yield: 91.0%

formic anhydride (1558-67-4) + L-leucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (108102-74-5) → 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)

Guidance literature:

In dichloromethane; at -10 - 0 ℃;

upstream raw materials:

formic acid

Z-Leu-OH

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

N-formyl-L-leucine

Downstream raw materials:

N-Formyl-L-leucine (S,E)-1-(Non-2-enyl)dodecyl Ester

(2S,3S,5S)-5-<<(S)-2-(Formylamino)-4-methylpentanoyl>oxy>-2-hexyl-3-hydroxyhexadecanoic Acid

(S)-3-Hexyl-5,6-dihydro-6-undecyl-2H-pyran-2-one

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

Refernces

Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy.

10.1021/ol000070a

The research focuses on the diastereoselective synthesis of (?)-tetrahydrolipstatin, a potent and irreversible inhibitor of pancreatic lipase, which has been marketed as an antiobesity agent under the name Xenical. The purpose of the study was to develop a novel synthetic route for this compound, emphasizing the importance of its biological activity, which is attributed to its γ-lactone moiety with specific antistereochemistry. The synthesis involves several key steps, including an asymmetric ester-derived titanium enolate anti-aldol reaction, a nitro-aldol reaction to append the C-2′ C11 side chain, and a diastereoselective reduction of a β-hydroxy ketone to an anti-1,3-diol functionality. The researchers successfully synthesized (?)-tetrahydrolipstatin with high yields and selectivity, setting three of the four asymmetric centers through asymmetric synthesis.