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 (2) and Methyl 1,1',1''- (3,4',5-stilbenyl)-1,6-hexanedioate (3) have been synthesized. Compound 3 is a new compound, synthetic yield is 88%, and purity is above 95% based on NMR integration. Both 2 and 3 are good candidates for biological evaluation. 3 was used as a precursor in the synthesis of resveratrol aliphatic acid, 8-(3',5'-dihydroxylstilbene-4''-oxy)-3,6-dioxocotanoic acid (9). First, 2 was hydrolyzed to resveratrol diester, 3,5-diacetyloxystilbene (4). 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 (/5), which was then hydrolyzed to afford 9 in total 43.6 % yield. Structures of all newly synthesized compounds were confirmed by 1H and 13C NMR spectroscopy.
","abstract_html":"<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 <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy.</p>","abstract_has_math":false,"creators":["Jing, Stanley Mofor"],"institution":null,"degree_name":"MS (Master of Science)","degree_level":"Thesis - unrestricted","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2011,"date_issued":"2011-12-17T08:00:00Z","date_published":"2011-12-17T08:00:00Z","updated_at":"2026-07-24T02:20:31Z","subjects":["resveratrol","phytoalexin","biological activity","bioavailability","stilbenoid","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Life Sciences"],"languages":[],"rights":["Copyright by the authors."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://dc.etsu.edu/etd/1382","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Jing, Stanley Mofor"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["1990-01-01T08:00:00Z"]},{"key":"dc:date.issued","label":"Date","values":["2011-12-17T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis - unrestricted"]},{"key":"thesis:degree_name","label":"Degree Name","values":["MS (Master of Science)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["resveratrol","phytoalexin","biological activity","bioavailability","stilbenoid","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Life Sciences"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["Copyright by the authors."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://dc.etsu.edu/context/etd/article/2573/viewcontent/JingS120311f.pdf","https://dc.etsu.edu/etd/1382"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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 (2) and Methyl 1,1',1''- (3,4',5-stilbenyl)-1,6-hexanedioate (3) have been synthesized. Compound 3 is a new compound, synthetic yield is 88%, and purity is above 95% based on NMR integration. Both 2 and 3 are good candidates for biological evaluation. 3 was used as a precursor in the synthesis of resveratrol aliphatic acid, 8-(3',5'-dihydroxylstilbene-4''-oxy)-3,6-dioxocotanoic acid (9). First, 2 was hydrolyzed to resveratrol diester, 3,5-diacetyloxystilbene (4). 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 (/5), which was then hydrolyzed to afford 9 in total 43.6 % yield. Structures of all newly synthesized compounds were confirmed by 1H and 13C NMR spectroscopy.
"]},{"key":"dc:title","label":"Title","values":["Synthesis of Resveratrol Esters and Aliphatic Acids."]}]}],"canonical_facts":{"dc:creator":["Jing, Stanley Mofor"],"dc:date.available":["1990-01-01T08:00:00Z"],"dc:date.issued":["2011-12-17T08:00:00Z"],"dc:description.abstract":["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 (2) and Methyl 1,1',1''- (3,4',5-stilbenyl)-1,6-hexanedioate (3) have been synthesized. Compound 3 is a new compound, synthetic yield is 88%, and purity is above 95% based on NMR integration. Both 2 and 3 are good candidates for biological evaluation. 3 was used as a precursor in the synthesis of resveratrol aliphatic acid, 8-(3',5'-dihydroxylstilbene-4''-oxy)-3,6-dioxocotanoic acid (9). First, 2 was hydrolyzed to resveratrol diester, 3,5-diacetyloxystilbene (4). 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 (/5), which was then hydrolyzed to afford 9 in total 43.6 % yield. Structures of all newly synthesized compounds were confirmed by 1H and 13C NMR spectroscopy.
"],"dc:identifier":["https://dc.etsu.edu/context/etd/article/2573/viewcontent/JingS120311f.pdf","https://dc.etsu.edu/etd/1382"],"dc:rights":["Copyright by the authors."],"dc:subject":["resveratrol","phytoalexin","biological activity","bioavailability","stilbenoid","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Life Sciences"],"dc:title":["Synthesis of Resveratrol Esters and Aliphatic Acids."],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis - unrestricted"],"thesis:degree_name":["MS (Master of Science)"]},"updated_at":"2026-07-24T02:20:31Z"}