Synthesis of 6-O-Octanoyl-1,2-O-isopropylidene-.ALPHA.-D-glucofuranose by Lipase-catalyzed Esterification in an Organic Solvent
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- Kobayashi Takashi
- Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University
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- Takahashi Tomoko
- Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University
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- Adachi Shuji
- Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University
Bibliographic Information
- Other Title
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- Synthesis of 6-O-Octanoyl-1,2-O-isopropylidene-α-D-glucofuranose by Lipase-catalyzed Esterification in an Organic Solvent
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Abstract
The synthesis of 6-O-octanoyl-1,2-O-isopropylidene-α-D-glucofuranose (C8-IpGlc) via the lipase-catalyzed esterification of 1,2-O-isopropylidene-α-D-glucofuranose (IpGlc) with octanoic acid was evaluated using ketones, nitriles, and tertiary alcohols as reaction media. Among the solvents assessed, acetone was the most effective solvent for the synthesis of C8-IpGlc at 50°C, without the formation of a by-product (a diester of IpGlc); the optimum molar ratio of octanoic acid:IpGlc was 2:1. Notwithstanding early-stage substrate inhibition by IpGlc at initial IpGlc concentrations greater than 250 mmol/L, an optimal product concentration of ca. 210 mmol/L (conversion = 53 % at 7 d) was achieved at longer reaction times by changing the initial IpGlc concentration from 25 to 800 mmol/L.
Journal
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- Journal of Oleo Science
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Journal of Oleo Science 61 (2), 75-79, 2012
Japan Oil Chemists' Society
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Details 詳細情報について
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- CRID
- 1390282679068373120
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- NII Article ID
- 130001882211
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- NII Book ID
- AA11503337
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- ISSN
- 13473352
- 13458957
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- NDL BIB ID
- 023388363
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed