Oxidation of sterols: Energetics of C?H and O?H bond cleavage

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F12%3A00376443" target="_blank" >RIV/61388955:_____/12:00376443 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.foodchem.2012.02.031" target="_blank" >http://dx.doi.org/10.1016/j.foodchem.2012.02.031</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.foodchem.2012.02.031" target="_blank" >10.1016/j.foodchem.2012.02.031</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Oxidation of sterols: Energetics of C?H and O?H bond cleavage

Popis výsledku v původním jazyce

Phytosterols, as components of human diet, received much attention because of their cholesterol-lowering and antioxidant properties. We have theoretically studied sterols oxidation in terms of O?H and C?H bond dissociation enthalpies (BDE). In 17 ?5- and?7-sterols, BDEs were obtained for reported sites of oxidation attack. Obtained results indicate that ?7-sterols are more susceptible to oxidation attack in comparison to ?5-sterols. In sterol nuclei, the lowest BDE was found for C7?H bond in ?5-sterolsand for C14?H in ?7-sterols. When ?5-sterol has a C=C double bond in the side chain, the lowest BDEs are usually found for C?H bonds in ?-positions to this bond. The homolytic cleavage of hydroxyl O?H bond requires larger energy in comparison to the studied C?H bonds. We have shown that the C?H bonds with lowest BDE values actually correspond to the dominant sites of oxidation attack.

Název v anglickém jazyce

Oxidation of sterols: Energetics of C?H and O?H bond cleavage

Popis výsledku anglicky

Phytosterols, as components of human diet, received much attention because of their cholesterol-lowering and antioxidant properties. We have theoretically studied sterols oxidation in terms of O?H and C?H bond dissociation enthalpies (BDE). In 17 ?5- and?7-sterols, BDEs were obtained for reported sites of oxidation attack. Obtained results indicate that ?7-sterols are more susceptible to oxidation attack in comparison to ?5-sterols. In sterol nuclei, the lowest BDE was found for C7?H bond in ?5-sterolsand for C14?H in ?7-sterols. When ?5-sterol has a C=C double bond in the side chain, the lowest BDEs are usually found for C?H bonds in ?-positions to this bond. The homolytic cleavage of hydroxyl O?H bond requires larger energy in comparison to the studied C?H bonds. We have shown that the C?H bonds with lowest BDE values actually correspond to the dominant sites of oxidation attack.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP208%2F11%2F0161" target="_blank" >GAP208/11/0161: Dynamika solvatovaných elektronů v molekulových klastrech: experiment a teorie</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Food Chemistry

ISSN

0308-8146

e-ISSN

—

Svazek periodika

133

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

6

Strana od-do

1435-1440

Kód UT WoS článku

000303847400045

EID výsledku v databázi Scopus

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