Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, 20-031, Lublin, Poland.
Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, 20-031, Lublin, Poland.
Talanta. 2023 Jan 1;251:123777. doi: 10.1016/j.talanta.2022.123777. Epub 2022 Aug 10.
for the analysis of cannabinoids in bio-matrices are continually improved to achieve best possible sensitivity in their detection and accurate quantification. It has been well documented that CBD cyclizes to Δ9-THC and Δ9-THC isomerizes to Δ8-THC under acidic conditions by means of a Lewis-acid-catalyzed process, causing difficulty in accurate quantification of Δ9-THC in the presence of CBD, of CBD itself and of Δ9-THC itself when these compounds have to be derivatized by acylation. The present paper shows that CBD cyclization and Δ9-THC isomerization can be blocked by tertiary amines or azines, which capture protons appearing in the derivatizing mixture during acylation. The efficiency of the described acylation of CBD depends on the time and temperature of the derivatizing process, whereas the degree of CBD acylation, i.e. the synthesis of mono- or di-acylate CBD derivative, depends on the mutual ratio of the cannabinoid, the acylating agent and the proton binding compound. The way of mono- and di-acyl CBD derivatives formation described in the paper has not been reported yet. The paper contains a comprehensive analytical characterization of two types of CBD acyl derivatives, CBD-TFA and CBD-Ac, obtained by NMR, GC-MS and LC-MS.
用于生物基质中大麻素分析的方法在不断改进，以实现检测的最佳灵敏度和准确的定量。已有充分的文献记载，CBD 在酸性条件下通过路易斯酸催化过程环化生成 Δ9-THC，Δ9-THC 异构化为 Δ8-THC，这导致在 CBD、CBD 本身和 Δ9-THC 本身存在时，难以准确定量 Δ9-THC，因为这些化合物在衍生化时必须进行酰化。本文表明，CBD 的环化和 Δ9-THC 的异构化可以被叔胺或脒捕获，这些化合物可以捕获酰化混合物中出现的质子。所描述的 CBD 酰化的效率取决于衍生化过程的时间和温度，而 CBD 酰化的程度，即单或二酰化 CBD 衍生物的合成，取决于大麻素、酰化剂和质子结合化合物的相互比例。本文描述的 CBD 单和二酰衍生物的形成方式尚未见报道。本文通过 NMR、GC-MS 和 LC-MS 对两种 CBD 酰基衍生物 CBD-TFA 和 CBD-Ac 进行了全面的分析表征。
