Student Theses and Dissertations

Date of Award

Spring 5-18-2024

Document Type

Thesis

Degree Name

B.A. with honors

Honors Designation

yes

Program of Study

Chemistry

Language

English

First Advisor

Edyta Greer

Abstract

Foul smelling compounds exist in waste products from sperm whales that arise from their cephalopod diet. A potential air-ocean interface photooxidation of these waste products convert the natural product ambrein to volatile breakdown products ambrox and 𝛾-dihydroionone. In contrast to their original odor, these products have a pleasant smell, and are therefore desirable in the perfume industry. Our density functional theory (DFT) studies pointed to singlet oxygen (1O2) oxidation of ambrein in an 'ene' reaction due to the structure of the products formed. In the absence of 1O2, a tetrahydropyran ring would have formed. However, when 1O2 reacts with ambrein in the ‘ene’ reaction, a tetrahydrofuran ring is formed instead, which is seen in the product ambrox. The mechanism proceeds with the loss of a hydrogen and oxygen atom, resulting in an oxide radical. A part of the molecule is expelled, and the resulting molecule then undergoes a reaction to form the tetrahydrofuran ring. The molecule then breaks apart into two, resulting in the two desired products: ambrox and 𝛾-dihydroionone. The results of these DFT studies are discussed.

Available for download on Monday, May 26, 2025

Share

COinS