We reported previously the microbial cu-oxidation of isopropyl end of capsaicin and of dihydrocapsaicin. To clarify the ω-oxidation on straight side chain of capsinoids, nonoylvanillylamide which shows same order of pungency as natural caysaicin was chosen as a substrate. When this compound was exposed to Aspergillus niger, 3 metabolites of vanillylamide were accumulated on expense of substrate or on expense of earlier accumulated metabolite. 3 metabolites were presumed as to be phenolic compounds by diazotized sulfanitic acid test. In a typical experiment, 1g of nonoylvanillylamide was dissolved in minimum amount of dimethyl-formamide and incubated in A. niger culture broth in 250r ml for 70 hours. Incubation was terminated by acidifying (pH about 3 by hydrochloric acid,`, After removal of mycelium with cheese cloth, the broth was extracted with ethyl acetate and worked out as usual method. 1.8g of extraction residue was obtained. The residue was applied over a silicic acid column and gradient elution system consisting of benzene and ethyl acetate was applied. Fractions of less polar metabolite were combined and removal of the solvent gave 400mg of crystalline compound. This compound showed the same pattern of U. V. absorption as shown by capsaicin. With comparison of NMR signals of this compound in deuterated DMSO, acetylation product in CDC₃, and authentic nonoylvanillylamide and acetylated nonoylvanillylamide, existence of ω-hydroxy group in the inetabolite was proved. Furthermore GC-mass spectral data backed up the proposed structure as 9-hydroxynonoylvanillylamide. For isolation of most polar metabolite of nonoylvanillvlamide, 1g of substrate was incubated for a prolonged period of time (150 hrs.). After working out as usual manner 1.2g of residue obtained was applied over silicic acid column and a gradient elution with benzene and ethyl acetate gave 200mg of noncrystalline compound Acidic nature was proved by bromeresol green test. Pattern of U.V. spectrum was same as that of substrate. NMR spectral data and GC-mass data showed the hydroxylation on the aliphatic portion of the side chain along with w-oxidation. Its possible structure is $lt;화학식생략$gt; We are investigating the exact position and configuration of newly introduced hydroxy group.