Honors Theses

Date of Award

Spring 5-8-2022

Document Type

Undergraduate Thesis

Department

Chemistry and Biochemistry

First Advisor

Nathan I. Hammer

Second Advisor

Ryan C. Fortenberry

Third Advisor

Hoang V. Le

Relational Format

Dissertation/Thesis

Abstract

The cannabinoids are a class of molecules endogenous to the cannabis plant. Their scientific relevance has increased in recent years due to the mercurial legal status of marijuana across the United States. Some of the most known are cannabidiol (CBD), δ9-tetrahydrocannabinol (δ9-THC), and δ8-THC due in large part to their widespread use, especially in states where marijuana and related products are legal. However, cannabigerolic acid (CBGA) is arguably the most important cannabinoid; it is enzymatically converted into other acidic cannabinoids, which subsequently undergo non-enzymatic processes (isomerization, thermal decarboxylation, oxidation, etc.) to synthesize further cannabinoids. Although there is a wealth of research regarding these compounds, there are not any examples in the literature of the analysis of the vibrational spectroscopic differences between them as they undergo the different conversion processes. Thus, the goal of this current research was to utilize Raman spectroscopy to collect high resolution spectra for each available cannabinoid in order to highlight key vibrational spectroscopic differences between them. These vibrational differences were subsequently analyzed in the context of the biosynthetic pathways stemming from CBGA. Density functional theory (DFT) calculations were also utilized to generate simulated spectra in order to evaluate the extent of agreement between experiment and theory. The results of this study demonstrate that key vibrational differences, particularly in the OH stretching region, could be identified between the spectra. Additionally, the overall agreement between experiment and theory was good, although it varied depending on the sample.

Available for download on Tuesday, April 30, 2024

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