Synthesis of lipophilic antioxidants by a lipase-B-catalyzed addition of peracids to the double bond of 4-vinyl-2-methoxyphenol
SPO/SPIRAL 4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The add...
Published in: | Journal of Agricultural and Food Chemistry |
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Main Authors: | , , , , , |
Other Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
HAL CCSD
2015
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Subjects: | |
Online Access: | https://hal.archives-ouvertes.fr/hal-01269365 https://doi.org/10.1021/acs.jafc.5b03551 |
Summary: | SPO/SPIRAL 4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The addition of peracids with 4-8 carbons in their alkyl chains led to the formation of two regioisomers, with the prevalence of hydroxyesters bearing a primary free hydroxyl (4c-4e). This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. In this case, only isomers 4f-4h were formed. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and it was found out that the 4-vinyl guaiacol antioxidant activity was significantly increased by grafting alkyl chains with 2-8 carbons. |
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