358730-99-1

Usage

Uses

Used in Biochemical Research:
Hexadecanoic-12-d acid(9CI) is used as a research compound for studying the metabolism and biological processes involving fatty acids. The incorporation of deuterium allows researchers to track the behavior and interactions of the molecule within biological systems, providing insights into the mechanisms of lipid metabolism and related pathways.
Used in Pharmaceutical Development:
Hexadecanoic-12-d acid(9CI) serves as a valuable tool in the development of pharmaceuticals targeting lipid-related disorders. Its isotopically labeled nature enables the investigation of drug interactions with fatty acid metabolism, aiding in the design of more effective and targeted therapies.
Used in Material Sciences:
Hexadecanoic-12-d acid(9CI) is utilized in the study of the properties and behavior of lipids in various materials, such as cosmetics, personal care products, and industrial applications. The deuterium labeling allows for a better understanding of the molecular interactions and stability of these materials, leading to the development of improved formulations and products.

Upstream product

• 57-10-3 1-hexadecylcarboxylic acid 
• 492-97-7 2,2'-Bithiophene 
• 10352-88-2 E-hept-2-enoic acid 
• 7383-19-9 hept-1-yn-3-ol 
• 790695-90-8 (R)-[10,10,11,11-2H₄]-1,12-hexadecandiol 
• 200504-46-7 (S)-hept-1-yn-3-yl acetate 
• 790695-76-0 (S)-(-)-3-methoxymethoxy-1-heptyne 
• 790695-91-9 (S)-[10,10,11,11-2H₄]-1,12-hexadecandiol 
• 152359-21-2 C₇H₁₂⁽²⁾H₂O₂ 
• 152359-30-3 (2S,3S)-1-iodo-<2,3-(2)H>-heptane 
• 152359-28-9 (2S,3S)-<2,3-(2)H>-heptanol 
• 152359-24-5 C₇H₁₂⁽²⁾H₂O₂ 
• 152359-22-3 (2R,3R)-1-iodo-<2,3-(2)H>-heptane 
• 152359-25-6 (2R,3R)-<2,3-(2)H>-heptanol 

Downstream Products

• 29848-79-1 methyl hexadecanoate-d31 
• 241157-04-0 tripalmitin-d₉₃ 
• 218956-22-0 d33-hexadecanethiol 
• 284474-73-3 1-hexadecyl-d33-ol 

Relevant academic research and scientific papers

Mild and Direct Multiple Deuterium-Labeling of Saturated Fatty Acids

We have established a mild and direct platinum on carbon (Pt/C)-catalyzed multi-deuterium labeling of various saturated fatty acids including bioactive compounds with high deuterium efficiencies in a mixed solvent of isopropyl alcohol and deuterium oxide

Deuterium kinetic isotope effects on the dissociation of a protein-fatty acid complex in the gas phase

Deuterium kinetic isotope effects (KIEs) are reported for the first time for the dissociation of a protein-ligand complex in the gas phase. Temperature-dependent rate constants were measured for the loss of neutral ligand from the deprotonated ions of the 1:1 complex of bovine β-lactoglobulin (Lg) and palmitic acid (PA), (Lg + PA)n- → Lgn- + PA, at the 6- and 7- charge states. At 25 °C, partial or complete deuteration of the acyl chain of PA results in a measurable inverse KIE for both charge states. The magnitude of the KIEs is temperature dependent, and Arrhenius analysis of the rate constants reveals that deuteration of PA results in a decrease in activation energy. In contrast, there is no measurable deuterium KIE for the dissociation of the (Lg + PA) complex in aqueous solution at pH 8. Deuterium KIEs were calculated using conventional transition-state theory with an assumption of a late dissociative transition state (TS), in which the ligand is free of the binding pocket. The vibrational frequencies of deuterated and non-deuterated PA in the gas phase and in various solvents (n-hexane, 1-chlorohexane, acetone, and water) were established computationally. The KIEs calculated from the corresponding differences in zero-point energies account qualitatively for the observation of an inverse KIE but do not account for the magnitude of the KIEs nor their temperature dependence. It is proposed that the dissociation of the (Lg + PA) complex in aqueous solution also proceeds through a late TS in which the acyl chain is extensively hydrated such that there is no significant differential change in the vibrational frequencies along the reaction coordinate and, consequently, no significant KIE.

Synthesis and use of stereospecifically deuterated analogues of palmitic acid to investigate the stereochemical course of the Δ11 desaturase of the processionary moth

Thaumetopoea pityocampa pheromone glands contain desaturases that, after several sequential reactions from palmitic acid, catalyze the formation of a unique enyne fatty acid, which is the immediate sex pheromone precursor. In this article, we describe the synthesis of different stereospecifically deuterium-labeled and isotopically tagged palmitic acid probes needed to decipher the stereochemical course of the T. pityocampa Δ11 desaturase. The synthesis of probes has been carried out by a chemoenzymatic route, in which the key step is the kinetic lipase-catalyzed resolution of racemic mixtures of secondary propargyl alcohols. The presence of the acetylenic bond simplifies the absolute configuration determination of the resolved alcohols. Moreover, it allows the introduction of the isotopic tag by deuteration. By use of the probes thus prepared, experimental evidence is presented that the Δ11 desaturase of T. pityocampa transforms palmitic acid into (Z)-11-hexadecenoic acid by removal of the pro-(R)-hydrogen atoms from both C11 and C12.

Synthesis of Deuterium Labelled (11S,12R)- and (11R,12S)--Palmitic Acids; a Facile Route to Highly Labelled Fatty Acids

Chiral, highly deuterated palmitic acids are synthesised from 2,2'-bithienyl in three steps by two alkylations and reductive desulfurisation for the introduction of twelve deuterium atoms.The chiral building blocks are obtained from α,β-unsaturated acids by enantiospecific reduction with broken cells of the microorganism Clostridium tyrobutyricum.