Determination of optical purity and absolute configuration of natural 12-hydroxystearic acid by the 1H NMR anisotropy method

被引：8
|
作者：
Murakami, Satoshi [1 ]
Satou, Kazuhiro [1 ]
Kijima, Taturo [1 ]
Watanabe, Masataka [1 ]
Izumi, Taeko [1 ]
机构：
[1] Yamagata Univ, Grad Sch Sci & Engn, Yonezawa, Yamagata 9928510, Japan
来源：
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY | 2011年 / 113卷 / 04期
关键词：
Absolute configuration; Anisotropy method; Chiral; 12-Hydroxystearic acid; NMR; 2-METHOXY-2-(1-NAPHTHYL)PROPIONIC ACID; ACETYLENE ALCOHOLS; ENANTIORESOLUTION;
D O I：
10.1002/ejlt.201000348
中图分类号：
TS2 [食品工业];
学科分类号：
0832 ;
摘要：
The enantiopure of (R)-(-) M alpha NPA was allowed to react with racemic 18-(tert-butyldimethylsilyloxy)-5-octadecayne- 7-ol which was derived from dodecane-1,12-diol, yielding diastereomeric esters mixture. These racemic esters were easily separated by HPLC on silica-gel. The absolute configurations of the first-eluted diastereomeric esters from the separated esters were determined using H-1 NMR anisotropy method. Analysis on H-1 NMR spectra and HPLC elution time of the synthesized esters and those of M alpha NP ester derived from natural methyl-12-hydroxystealate showed that the absolute configuration of natural 12-hydroxystearic acid was R form, and the enantiomeric excess was over 99%.
引用
收藏
页码：450 / 458
页数：9
相关论文
共 50 条
  • [41] 1H NMR Reassignment for Z/E-Benzomalvins B and Absolute Configuration of Benzomalvin C
    Rong Chao
    Yan-Wei Wu
    Ling Lu
    Wei-Feng Xu
    Chang-Yun Wang
    Chang-Lun Shao
    Chemistry of Natural Compounds, 2021, 57 : 343 - 345
  • [42] Absolute quantification of dehydroacetic acid in processed foods using quantitative 1H NMR
    Ohtsuki, Takashi
    Sato, Kyoko
    Furusho, Noriko
    Kubota, Hiroki
    Sugimoto, Naoki
    Akiyama, Hiroshi
    FOOD CHEMISTRY, 2013, 141 (02) : 1322 - 1327
  • [43] Direct enantiomeric purity determination of the chiral anesthetic drug bupivacaine by 1H NMR spectroscopy
    Hanna, GM
    PHARMAZIE, 2001, 56 (04): : 314 - 317
  • [44] Determination of the purity of pharmaceutical reference materials by 1H NMR using the standardless PULCON methodology
    Monakhova, Yulia B.
    Kohl-Himmelseher, Matthias
    Kuballa, Thomas
    Lachenmeier, Dirk W.
    JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2014, 100 : 381 - 386
  • [45] Assignment of the absolute configuration of hydroxy acids using 1H NMR spectroscopy: a simple and rapid approach
    Mishra, Sandeep Kumar
    Suryaprakash, N.
    TETRAHEDRON-ASYMMETRY, 2017, 28 (02) : 250 - 256
  • [46] 1H NMR Reassignment for Z/E-Benzomalvins B and Absolute Configuration of Benzomalvin C
    Chao, Rong
    Wu, Yan-Wei
    Lu, Ling
    Xu, Wei-Feng
    Wang, Chang-Yun
    Shao, Chang-Lun
    CHEMISTRY OF NATURAL COMPOUNDS, 2021, 57 (02) : 343 - 345
  • [47] Absolute Configuration of Ketone Cyanohydrins by 1H NMR: The Special Case of Polar Substituted Tertiary Alcohols
    Louzao, Iria
    Garcia, Rosa
    Manuel Seco, Jose
    Quinoa, Emilio
    Riguera, Ricardo
    ORGANIC LETTERS, 2009, 11 (01) : 53 - 56
  • [48] A validated 1H NMR method for the determination of the degree of deacetylation of chitosan
    Lavertu, M
    Xia, Z
    Serreqi, AN
    Berrada, M
    Rodrigues, A
    Wang, D
    Buschmann, MD
    Gupta, A
    JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2003, 32 (06) : 1149 - 1158
  • [49] Synthesis of 2-arloxypropanoic acids analogues of clofibric acid and assignment of the absolute configuration by 1H NMR spectroscopy and DFT calculations
    Ammazzalorso, Alessandra
    Bettoni, Giancarlo
    De Filippis, Barbara
    Fantacuzzi, Marialuigia
    Giampietro, Letizia
    Giancristofaro, Antonella
    Maccallini, Cristina
    Re, Nazzareno
    Amoroso, Rosa
    Coletti, Cecilia
    TETRAHEDRON-ASYMMETRY, 2008, 19 (08) : 989 - 997
  • [50] MTPA vs MPA in the determination of the absolute configuration of chiral alcohols by H-1 NMR
    Latypov, SK
    Seco, JM
    Quinoa, E
    Riguera, R
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8569 - 8577
12345