151763-75-6

Basic information

• Product Name: ETHYL (R)-3-HYDROXY-TETRADECANOATE
• Synonyms: TETRADECANOIC ACID, 3-HYDROXY-, ETHYL ESTER, (R);ETHYL (R)-3-HYDROXY-TETRADECANOATE
• CAS NO: 151763-75-6
• Molecular Formula: C₁₆H₃₂O₃
• Molecular Weight: 272.42
• Mol File: 151763-75-6.mol

Chemical Properties

• Boiling Point: 374.2±15.0 °C(Predicted)
• Appearance: /
• Density: 0.926±0.06 g/cm3(Predicted)
• PKA: 14.41±0.20(Predicted)
• CAS DataBase Reference: ETHYL (R)-3-HYDROXY-TETRADECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (R)-3-HYDROXY-TETRADECANOATE(151763-75-6)
• EPA Substance Registry System: ETHYL (R)-3-HYDROXY-TETRADECANOATE(151763-75-6)

Safety Data

• Hazardous Substances Data: 151763-75-6(Hazardous Substances Data)

Upstream product

• 17049-50-2 n-decyl magnesium bromide 
• 112083-63-3 ethyl (-)-(2S)-oxirane-2-acetate 
• 74124-22-4 ethyl 3-oxotetradecanoate 
• 112-29-8 1-bromo dodecane 
• 112-54-9 Dodecanal 
• 335153-25-8 (E)-Tetradec-2-enoic acid ethyl ester 
• 112100-39-7 (S)-4-iodo-3-hydroxy-butyric acid ethyl ester 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 
• 87357-66-2 phrnacyl (R)-3-(benzyloxy)tetradecanoate 
• 91681-56-0 (3R)-3-dodecanoyloxytetradecanoic acid 
• 339316-63-1 (R)-3-Dodecanoyloxy-tetradecanoic acid 2-oxo-2-phenyl-ethyl ester 
• 87357-65-1 (3R)-3-hydroxytetradecanoic acid phenacyl ester 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 104872-04-0 Orlistat 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 

Relevant articles and documents

BIFUNCTIONAL COMPOUND AND ITS USE IN IMMUNOTHERAPY

The invention relates to a bifunctional compound that is, on one side, an agonist of the TLR4 and, on the other side, an important inhibitor of the PSMA. Said compound is useful in immunotherapy for the treatment and/or prevention of prostate cancer. Therefore, the invention also relates to the use of the compound and to the pharmaceutical composition comprising it.

SYNTHETIC DERIVATIVES OF MPL AND USES THEREOF

In one aspect, the present disclosure provides compounds of formulae (I) and (II). In another aspect, a compound of formula (I) or (II) is formulated into compositions with an antigen, optionally with a vesicle. In some embodiments, compositions are administered intramuscularly.

BETA-LACTONE COMPOUNDS

The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

Synthesis of novel &β-lactone inhibitors of fatty acid synthase

Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report on the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a β-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the α- and β-alkyl chains, their chemical composition, and amino ester substitutions were altered and the resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display an increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings support the idea that an orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.

Highly enantioselective hydrogenation of β-alkyl and β-(ω-chloroalkyl) substituted β-keto esters

Highly enantioselective hydrogenation of β-alkyl and β-(ω-chloroalkyl) substituted β-keto esters was achieved with Ru catalysts based on chiral diphosphines in EtOH at 50°C under 50-bar initial hydrogen pressure, affording the corresponding β-hydroxy esters in >98% ee. Copyright Taylor & Francis Group, LLC.

Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase

Concise syntheses of orlistat (Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the α-side chain. Versatile strategies for modifying the δ-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.

An efficient synthesis of (R)-3-hydroxytetradecanoic acid

A short, efficient synthesis of (R)-3-hydroxytetradecanoic acid, a key component of bacterial endotoxins, using (R)-oxirane acetic acid ethyl ester as the source of chirality is described. The method is general and can be used in the preparation of other chiral 3-hydroxy acids.