Chemical Analysis of Vitamin A and Analogs
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Date
2013-05
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The Ohio State University
Abstract
Vitamin A plays an important role in growth, vision, epithelial differentiation, immune function, and reproduction. However, vitamin A metabolites like retinoic acid (RA) pose many toxic effects in the body. Certain retinoid drugs like N-(4-hydroxyphenyl)retinamide (4-HPR) have shown promise treating epithelial cancers. Further research into the nonhydrolyzable analog, 4-hydroxybenzylretinone (4-HBR), have determined that it is just as potent but without any of the residual toxicity associated with RA. A new synthetic method for this drug was created, using a para-methyl benzyl phenyl ether as protecting group for the terminal phenol. Synthetic efficiency was also increased by the development of a larger scale synthesis for the expensive starting retinoid, retinal. This new method can successfully synthesize 4-HBR at a lower cost with good yields. This is useful for future chemical and biological studies of the retinoid.
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Keywords
Vitamin A, Cancer, Pharmacology, Organic Synthesis, 4-HBR, Chemistry