71271-24-4

Basic information

• Product Name: DL-2-HYDROXYDECANOIC ACID METHYL ESTER
• Synonyms: 2-HYDROXY C10:0 METHYL ESTER;METHYL 2-HYDROXYDECANOATE;METHYL ALPHA-HYDROXYCAPRATE;DL-2-HYDROXYDECANOIC ACID METHYL ESTER;α-hydroxycapric acid methyl ester;2-Hydroxycapric acid methyl ester;2-Hydroxydecanoic acid methyl ester
• CAS NO: 71271-24-4
• Molecular Formula: C₁₁H₂₂O₃
• Molecular Weight: 202.29
• Mol File: 71271-24-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 249 °C at 760 mmHg
• Flash Point: 103.2 °C
• Appearance: /
• Density: 0.956 g/cm³
• Vapor Pressure: 0.00377mmHg at 25°C
• Refractive Index: 1.444
• Storage Temp.: −20°C
• CAS DataBase Reference: DL-2-HYDROXYDECANOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-HYDROXYDECANOIC ACID METHYL ESTER(71271-24-4)
• EPA Substance Registry System: DL-2-HYDROXYDECANOIC ACID METHYL ESTER(71271-24-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 71271-24-4(Hazardous Substances Data)

Usage

Biochem/physiol Actions

α-hydroxycapric acid methyl ester is a medium chain saturated hydroxy fatty acid. Enantiomeric mixtures of 2-OH-DA methyl ester may be used to evaluate hydroxyl FA enantiomer separation and detection technologies.

InChI:InChI=1/C11H22O3/c1-3-4-5-6-7-8-9-10(12)11(13)14-2/h10,12H,3-9H2,1-2H3

Upstream product

• 20487-42-7 2-methoxy-decanoic acid methyl ester 
• 5393-81-7 DL-2-hydroxydecanoic acid 
• 7367-85-3 methyl (E)-dec-2-enoate 
• 67-56-1 methanol 
• 124-19-6 nonan-1-al 
• 124838-34-2 1,1,1-tris(methylthio)-2-decanol 

Downstream Products

• 70267-29-7 (S)-2-Hydroxydecanoic acid 
• 85398-16-9 (R)-2-Hydroxydecansaeuremethylester 
• 81623-66-7 (+)-1,2-epoxy-decane 
• 67210-36-0 (R)-(+)-1,2-epoxydecane 

Relevant articles and documents

Gas chromatography/electron-capture negative ion mass spectrometry for the quantitative determination of 2- and 3-hydroxy fatty acids in bovine milk fat

2- and 3-hydroxy fatty acids (2- and 3-OH-FAs) are bioactive substances reported in sphingolipids and bacteria. Little is known of their occurrence in food. For this reason, a method suitable for the determination of OH-FAs at trace levels in bovine milk fat was developed. OH-FAs (and conventional fatty acids in samples) were converted into methyl esters and the hydroxyl group was derivatized with pentafluorobenzoyl (PFBO) chloride to give PFBO-O-FA methyl esters. These derivatives with strong electron affinity were determined by gas chromatography interfaced to mass spectrometry using electron-capture negative ion in the selected ion monitoring mode (GC/ECNI-MS-SIM). This method proved to be highly sensitive and selective for PFBO-O-FA methyl esters. For the analysis of samples, two internal standards were used. For this purpose, 9,10-dideutero-2-OH-18:0 methyl ester (ISTD-1) from 2-OH-18:1(9c) methyl ester as well as the ethyl ester of 3-PFBO-O-12:0 (ISTD-2) was synthesized. ISTD-1 served as a recovery standard whereas ISTD-2 was used for GC/MS measurements. The whole-sample cleanup consisted of accelerated solvent extraction of dry bovine milk, addition of ISTD 1, saponification, conversion of fatty acids into methyl esters by use of boron trifluoride, separation of the methyl esters of OH-FAs from nonsubstituted FAs on activated silica, conversion of OH-FAs methyl esters into PFBO-O-FA methyl esters, addition of ISTD-2, and measurement by GC/ECNI-MS-SIM. By this method, ten OH-FAs were quantified in bovine milk fat with high precision in the range from 0.02 ± 0.00 to 4.49 ± 0.29 mg/100 g of milk fat.

Synthesis of intermediates in the preparation of ACAT inhibitors

This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.

Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals

In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.