Octane-1,3-diol and its derivatives from pear fruits

 In extracts obtained by liquid-liquid extraction from seven pear (Pyrus communis L.) cultivars, octane-1,3-diol, 5(Z)octene-1,3-diol, methyl 3-hydroxyoctanoate, ethyl 3-hydroxyoctanoate and ethyl 5(Z)-3-hydroxyoctenoate were identified by capillary gas chromatography-mass spectrometry. Evaluation of the absolute configuration was achieved by multidimensional gas chromatography, using a polar achiral column (DB-Wax) and a chiral main column (2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-β-cyclodextrin/OV 1701). Comparison of retention times of synthesized optically enriched reference compounds with those of isolated diols and hydroxy esters revealed (R)-configurations for the 3-hydroxy derivatives, exhibiting enantiomeric excesses greater than 99%. In addition, (2S, 4R)- and (2R, 4R)-2-methyl-4-pentyl-1,3-dioxane as well as (2S, 4R)- and (2R, 4R)-2-methyl-4-(2′(Z)-pentenyl)-1,3-dioxane, products formed by acetaldehyde and octane-1,3-diol or 5(Z)-octene-1,3-diol, respectively, were detected in pear fruits. Received: 13 February 1997