Synthesis of Resveratrol Esters and Aliphatic Acids.

<p>Resveratrol (RV) is a naturally occurring phytoalexin of the stilbenoid family produced by some plant species, and present in grape skin, peanuts, and red wine. It has been found to exhibit anti-cancer, anti-inflammatory, anti-viral, anti-aging, cardio protective, and anti-oxidant properties. Bioavailability is a huge setback that limits the potentials of RV. As a result, efforts have been made to design and synthesize RV esters and aliphatic acids in an attempt to increase its bioavailability, solubility in water, and possibly improving its biological activities. Resveratrol esters, 3,5,4'-triacetyloxystilbene <b>(2)</b> and Methyl 1,1',1''- (3,4',5-stilbenyl)-1,6-hexanedioate <b>(3)</b> have been synthesized. Compound <b>3</b> is a new compound, synthetic yield is 88%, and purity is above 95% based on NMR integration. Both <b>2</b> and <b>3</b> are good candidates for biological evaluation. <b>3</b> was used as a precursor in the synthesis of resveratrol aliphatic acid, 8-(3',5'-dihydroxylstilbene-4''-oxy)-3,6-dioxocotanoic acid <b>(9)</b>. First, 2 was hydrolyzed to resveratrol diester, 3,5-diacetyloxystilbene <b>(4)</b>. Mitsunobu reaction of 4 and methyl 8-hydroxy-3,6-dioxooctanoate (7) was then carried out to afford methyl 8-(3',5'-diacetyoxystilben-4''-oxy)-3.6-dioxooctanoate <b>(/5)<b>, which was then hydrolyzed to afford <b>9</b> in total 43.6 % yield. Structures of all newly synthesized compounds were confirmed by ¹H and ¹³C NMR spectroscopy.</p>

Name thesis:degree_name

MS (Master of Science)

Level thesis:degree_level

Thesis - unrestricted

Discipline thesis:degree_discipline

Chemistry

Year dc:date.issued

2011

Author dc:creator

• Jing, Stanley Mofor

• resveratrol
• phytoalexin
• biological activity
• bioavailability
• stilbenoid
• Biochemistry
• Biochemistry, Biophysics, and Structural Biology
• Life Sciences

Statement dc:rights

• Copyright by the authors.

Repository record dc:identifier

https://dc.etsu.edu/etd/1382

OAI identifier oai:identifier

oai:dc.etsu.edu:etd-2573