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Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol From D-sorbitol and Cinnamic Acid Esters

Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol From D-sorbitol and Cinnamic Acid Esters

Jung-Ho Kim, Shashi Kant Bhatia, Dongwon Yoo, Hyung Min Seo, Da-Hye Yi, Hyun Joong Kim, Ju Hee Lee, Kwon-Young Choi, Kwang Jin Kim, Yoo Kyung Lee, Yung-Hun Yang

Appl Biochem Biotechnol. 2015 May;176(1):244-52.

PMID: 25809993

Abstract:

To overcome the poor properties of solubility and stability of cinnamic acid, cinnamate derivatives with sugar alcohols were produced using the immobilized Candida antarctica lipase with vinyl cinnamate and D-sorbitol as substrate at 45 °C. Immobilized C. antarctica lipase was found to synthesize 6-O-cinnamoyl-sorbitol and confirmed by HPLC and (1)H-NMR and had a preference for vinyl cinnamate over other esters such as allyl-, ethyl-, and isobutyl cinnamate as co-substrate with D-sorbitol. Contrary to D-sorbitol, vinyl cinnamate, and cinnamic acid, the final product 6-O-cinnamoyl-sorbitol was found to have radical scavenging activity. This would be the first report on the biosynthesis of 6-O-cinnamoyl-sorbitol with immobilized enzyme from C. antarctica.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3098928	Vinyl cinnamate		3098-92-8	Price

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