Chemical Properties
light yellow powder
Uses
8-Hydroxyoctanoic Acid is an intermediate in the synthesis of mono-carboxy-isooctyl-phthalate (M525590). 8-Hydroxyoctanoic Acid is also used as a reagent in the synthesis of histone deacetylases (HDAC) inhibitors with an N-formyl hydroxylamine head group which are promising targets for cancer chemotherapy.
Definition
ChEBI: An omega-hydroxy fatty acid that is caprylic acid in which one of the hydrogens of the terminal methyl group is replaced by a hydroxy group.
General Description
8-Hydroxyoctanoic acid is one of the constituents of ‘‘Royal jelly′′ acid found in herbhoneys and genuine honeys.
Synthesis
GENERAL PROCEDURE: All catalytic activity testing experiments were carried out in Schlenk tubes (50 mL) equipped with a condenser. 8-Hydroxycaprylic acid (HCA) was prepared by HDO oxidation reaction in alkaline aqueous medium using H2O2 as oxidant. The typical reaction procedure was as follows: first, the aliphatic diol (0.5 mmol) was weighed and dispersed with catalyst (25 mg) in deionized water (3.5 mL) in a Schlenk tube. Subsequently, 30% H2O2 (0.75 mL) and 0.5 M NaOH (0.75 mL) were added to the above mixture. The Schlenk tubes were placed in an oil bath preheated to 353 K and reacted for different time intervals under continuous magnetic stirring (500 rpm). After completion of the reaction, a portion of the reaction solution was taken and diluted 20-fold with 10 mM aqueous H2SO4 and the catalyst was removed by passing it through a 0.20 μm filter (Milex-LG). The resulting filtrate was analyzed by high performance liquid chromatography (HPLC, WATERS 600) on an Aminex HPX-87H column (Bio-Rad Laboratories, Inc.) with a refractive index detector. An aqueous solution of 10 mM H2SO4 was used as the eluent at a flow rate of 0.5 mL/min, and the column temperature was maintained at 323 K. The conversion and yield were determined by the calibration curve method for commercial products.
References
[1] Catalysis Today, 2016, vol. 265, p. 231 - 239
