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Chemical Synthesis and Isolation of trans ‐Palmitoleic Acid ( trans ‐C16:1 n‐7) Suitable for Nutritional Studies
European Journal of Lipid Science and Technology ( IF 1.8 ) Pub Date : 2020-05-19 , DOI: 10.1002/ejlt.201900409
Etienne Guillocheau 1, 2 , Gaëtan Drouin 1 , Daniel Catheline 1 , Clément Orione 3 , Philippe Legrand 1 , Vincent Rioux 1
Affiliation  

Trans‐palmitoleic acid (trans‐9 C16:1, or trans‐C16:1 n‐7, TPA) is typically found in ruminant‐derived foods (milk and meat). Of note, previous epidemiological studies associated high levels of circulating TPA with a lower risk of type 2 diabetes and metabolic syndrome in humans. At the current time, TPA intakes in humans are ensured by ruminant‐derived foods. However, due to the very low commercial availability of TPA, there are no supplementation studies carried out so far. Therefore, the ability for dietary TPA to prevent type 2 diabetes and metabolic syndrome has never been experimentally assessed. Here, we report a method (among others) to get dozens of grams of pure TPA as ethyl ester, to perform dedicated supplementation studies. For that purpose, we started from food sources containing high amounts of cis‐palmitoleic acid (cis‐9 C16:1, or cis‐C16:1 n‐7, CPA), dealing with fatty acids ethyl esters all along with the experiment. CPA was purified with flash LC, then submitted to a cis/trans isomerization step. Finally, TPA was separated from CPA by low‐temperature crystallization in methanol. The final product was fully characterized by 1H and 13C nuclear magnetic resonance spectrometry. We were able to produce approx. 70 g of 85%‐purity TPA suitable for nutritional studies.

中文翻译:

适用于营养研究的反式棕榈油酸 (trans-C16:1 n-7) 的化学合成和分离

反式棕榈油酸(反式 9 C16:1 或反式 C16:1 n-7,TPA)通常存在于反刍动物源食品(牛奶和肉类)中。值得注意的是,之前的流行病学研究表明,高水平的循环 TPA 与人类 2 型糖尿病和代谢综合征的风险较低有关。目前,人类对 TPA 的摄入量由反刍动物源食品保证。然而,由于 TPA 的商业可用性非常低,到目前为止还没有进行补充研究。因此,从未对膳食 TPA 预防 2 型糖尿病和代谢综合征的能力进行过实验评估。在这里,我们报告了一种获得数十克纯 TPA 作为乙酯的方法(以及其他方法),以进行专门的补充研究。为此,我们从含有大量顺式棕榈油酸(顺式 9 C16:1,或 cis-C16:1 n-7, CPA),在实验中一直处理脂肪酸乙酯。CPA 用快速液相色谱纯化,然后进行顺式/反式异构化步骤。最后,通过在甲醇中低温结晶将 TPA 与 CPA 分离。最终产品通过 1H 和 13C 核磁共振光谱进行了充分表征。我们能够生产大约。70 克 85% 纯度的 TPA,适用于营养研究。
更新日期:2020-05-19
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