17746-06-4

Usage

Uses

Used in Pharmaceutical Industry:
Tridecanoyl chloride is used as a synthetic intermediate for the production of 5α-Dihydrotestosterone Tridecanoate-d3 (D454172), a labeled compound that aids in the study and analysis of anabolic steroids, specifically Dihydrotestosterone Tridecanoate (D454170) and Androstanolone (A637540). This application is crucial for research and development in the field of anabolic steroids and their potential therapeutic uses.

InChI:InChI=1/C13H25ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13(14)15/h2-12H2,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 638-53-9 tridecanoic acid 
• 112-52-7 1-chlorododecane 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 54889-72-4 methyl 3-oxopentadecanoate 
• 2345-27-9 tetradecan-2-one 
• 112578-72-0 tridecanoic acid p-toluidide 
• 55469-24-4 1-(4-methoxyphenyl)tridecan-1-one 
• 142674-35-9 tridecanoyl carnitine 
• 129742-26-3 Tridecanoic acid 2,3,5-trimethyl-4,6-bis-tridecanoylamino-phenyl ester 
• 96515-55-8 Tridecanoic acid 4-[(E)-4'-(4-tridecanoyloxy-phenyl)-[2,2']bi[[1,3]dithiolylidene]-4-yl]-phenyl ester 
• 59891-27-9 1,3-Ditridecanoin 
• 136386-10-2 2-fluoro-4-n-tridecanoyloxybenzoic acid 
• 24938-64-5 C₄₆H₆₆N₄O₄ 

Relevant academic research and scientific papers

Synthesis of 6- and 9-ethyloctadecanoic acids

Specific branched fatty acids are of great interest in the search for a new type of drug penetration enhancers across human skin for transdermal drug delivery and in gaining an understanding of structure-activity relationships with skin lipids. A convenient synthesis has therefore been developed especially for ethyloctadecanoic acids. The successful syntheses of 6- and 9-ethyloctadecanoic acids are reported here.

Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis

We have analyzed the abundance of bacterial sulfonosphingolipids, including rosette-inducing factors (RIFs), in seven bacterial prey strains by using high-resolution tandem mass spectrometry (HRMS2) and molecular networking (MN) within the Glob

Characterization of the molecular packing, thermotropic phase behaviour and critical micellar concentration of a homologous series of N-acyltaurines (n = 9–18). PXRD, DSC and fluorescence spectroscopic studies

N-acyltaurines (NATs) are amides of fatty acids that can be structurally related to endocannabinoids. They show interesting physiological and pharmacological properties. We have synthesized a homologous series of NATs with saturated acyl chains (n = 9–18) and investigated their supramolecular structure and thermotropic phase transitions by powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC). The d-spacings obtained from PXRD increase linearly with chain length with an increment of ～0.847 ? per additional CH2 moiety suggesting that NATs adopt a tilted bilayer structure with similar packing in crystal lattice. Results obtained from DSC studies indicate that the endothermic transition temperature (Tt) of NATs showed a gradually increasing trend with increasing acyl chain length. The enthalpy (ΔHt) and entropy (ΔSt) of transition show odd-even alternations with odd-chain compounds having higher values than the even-chain compounds. The critical micellar concentration (CMC) of NATs was determined in water at room temperature by fluorescence spectroscopy by monitoring the spectral changes of 8-anilinonaphthalene-1-sulfonic acid (ANS). The CMCs of NATs were found to decrease with increase in acyl chain length. The present results provide a thermodynamic and structural basis for investigating the interaction of NATs with other membrane lipids and proteins, which in turn can shed light in understanding how they function in vivo (in biological membranes).

SUGAR FATTY ACID ESTER AND OIL GELLING AGENT

PROBLEM TO BE SOLVED: To provide a compound that can gel various oils. SOLUTION: The present invention provides a compound containing 1,5-anhydro-D-glucitol fatty acid ester, represented by formula (1), or 1,5-anhydro-D-mannitol fatty acid ester, and a gelling agent containing the compound. (R1 independently represent an acyl group derived from a C10, 11 or 13-22 linear saturated fatty acid). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Stereoselective synthesis of unnatural (2S, 3S)-6-hydroxy-4-sphingenine-containing sphingolipids

6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using an underexplored hydrozirconation-transmetalation reaction and an unusual three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6-hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labeled derivative suitable for future biological studies.

Mesogenic 3,6-bis(4-hydroxyphenyl)-1,2,4,5-tetrazine alkanoate esters

A novel series of 3,6-bis(4-hdroxyphenyl)-1,2,4,5-tetrazine alkanoate esters were synthesized and their mesogenic properties were studied using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). The impact of changing the tail-core linkage from alkyl or alkoxy to ester is profound. Compared to the alkyl or alkoxy linkages, the ester linkage reduced mesogenic properties. Short-tailed compounds are non mesogenic (4a-4e), while long-tailed compounds (4f-4r) exhibit nematic phases. Unlike the alkyl or alkoxy tail series, none of the 18 presented esters in this series exhibits a smectic phase.

Synthesis, antimicrobial activity and in silico studies on thymol esters

Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA

N-Acyl-β-alanines (NABAs) are structural homologues of N-acylglycines (NAGs) and N-acyl-γ-aminobutyric acids (NAGABAs), and achiral isomers of N-acylalanines, which are all present in mammalian brain and other tissues and modulate activity of biological receptors with various functions. In the present study, we synthesized and characterized a homologous series of NABAs bearing saturated acyl chains (n = 8-20) and investigated their supramolecular organization and thermotropic phase behavior. In differential scanning calorimetric (DSC) studies, most of the NABAs gave one or two minor transitions before the main chain-melting phase transition in the dry state as well as upon hydration with water, but gave only a single transition when hydrated with buffer (pH 7.6). Transition enthalpies (ΔHt) and entropies (ΔSt), obtained from the DSC studies showed linear dependence on the chain length in the dry state and upon hydration with buffer, whereas odd-even alteration was observed when hydrated with water. The crystal structures of N-lauroyl-β-alanine (NLBA) and N-myristoyl-β-alanine (NMBA) were solved in monoclinic system in the P21/c space group. Both NLBA and NMBA were packed in tilted bilayers with head-to-head (and tail-to-tail) arrangement with tilt angles of 33.28° and 34.42°, respectively. Strong hydrogen bonding interactions between [sbnd]COOH groups of the molecules from opposite leaflets as well as N[sbnd]H?O hydrogen bonds between the amide groups from adjacent molecules in the same leaflet as well as dispersion interactions between the acyl chains stabilize the bilayer structure. The d-spacings calculated from powder X-ray diffraction studies showed odd-even alteration with odd-chain length compounds exhibiting higher values as compared to the even-chain length ones and the tilt angles calculated from the PXRD data are higher for the even chain NABAs. These observations are relevant to developing structure-activity relationships for these amphiphiles and understand how NABAs differ from their homologues and isomers, namely NAGs, NAGABAs, and N-acylalanines.

Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy

(Chemical Equation Presented) In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.

An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues

Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.