Production of Saturated Acyl l-Ascorbate by Immobilized Lipase Using a Continuous Stirred Tank Reactor

6-O-Decanoyl, 6-O-dodecanoyl, or 6-O-tetradecanoyl l-ascorbate was continuously produced at 50 °C using a continuous stirred tank reactor (CSTR) with an immobilized lipase, Chirazyme L-2 C2, from Candida antarctica. Acetone was used as the reaction medium. For each saturated acyl l-ascorbate, the pr...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2003-07, Vol.51 (16), p.4628-4632
Main Authors: Watanabe, Yoshiyuki, Kuwabara, Ko, Adachi, Shuji, Nakanishi, Kazuhiro, Matsuno, Ryuichi
Format: Article
Language:English
Subjects:
acetone
Acylation
Ascorbic Acid - analogs & derivatives
Ascorbic Acid - analysis
Ascorbic Acid - metabolism
Bioreactors
Candida antarctica
Enzymes, Immobilized
Fatty Acids - analysis
Fatty Acids - metabolism
Free Radical Scavengers
Lipase - metabolism
Pseudozyma antarctica
Solubility
soybean oil
triacylglycerol lipase
water solubility
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Summary:6-O-Decanoyl, 6-O-dodecanoyl, or 6-O-tetradecanoyl l-ascorbate was continuously produced at 50 °C using a continuous stirred tank reactor (CSTR) with an immobilized lipase, Chirazyme L-2 C2, from Candida antarctica. Acetone was used as the reaction medium. For each saturated acyl l-ascorbate, the productivity of ca. 60 g/L reactor/day was achieved for at least 11 days. The solubility of the saturated acyl l-ascorbate in the soybean oil or water was measured at various temperatures. The solubilities in both the soybean oil and the water were higher for l-ascorbate with a shorter acyl chain. The acyl chain dependence of the solubility in water was stronger than that of the solubility in soybean oil. The temperature dependences of the solubility in both soybean oil and water could be expressed by the van't Hoff equation, and the dissolution enthalpy (ΔH) values for the soybean oil and water were about 20 and 90 kJ/mol, respectively, irrespective of the acyl chain length. The radical scavenging activities of l-ascorbic acid and the saturated acyl l-ascorbates against 1,1-diphenyl-2-picrylhydrazyl free radical were ca. 95% for all of the compounds, and the introduction of a saturated acyl group to the l-ascorbic acid did not affect the activity. Keywords: Acyl l-ascorbate; immobilized lipase; continuous stirred tank reactor; solubility; radical scavenging activity
ISSN:0021-8561
1520-5118
DOI:10.1021/jf030076p