Production and properties of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid conversion by Pseudomonas aeruginosa
✍ Scribed by Tsung Min Kuo; Gerhard Knothe
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 107 KB
- Volume
- 106
- Category
- Article
- ISSN
- 1438-7697
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✦ Synopsis
Abstract
This study was undertaken to produce a novel antifungal compound, 7,10,12‐trihydroxy‐8(E)‐octadecenoic acid (7,10,12‐THOD), in large quantities for determining its properties by use of crude ricinoleic acid as converted by Pseudomonas aeruginosa NRRL B‐23260. A useful reactor process was developed by employing a unique aeration mechanism and a new agitation device. The aeration mechanism involved a filtered airflow constantly supplied from the top through two ports on the headplate at 220 mL/min and at varied rates as needed and regulated through a bottom sparger, to control foaming. The agitation device combined a marine impeller and an open turbine to overcome the early phase of oxygen depletion and enhance production yields. A yield of 40% was achieved after 77 h of reaction when down‐stream processing of the bioproduct was most suitable. 7,10,12‐THOD was crystallized from ethyl acetate extracts of the reactor broth following a sequential cooling process to −20 °C. The melting point of 7,10,12‐THOD was 94.5–95.0 °C. The ^1^H‐ and ^13^C‐NMR signals of all protons and carbons in the 2(E)‐ene‐1,4,6‐triol moiety of 7,10,12‐THOD were now assigned, also with the aid of various 2D techniques. 7,10,12‐THOD was found to exhibit a unique surface‐active property. This study provides basic information and process technology for potential new uses of 7,10,12‐THOD.