Lipid extracts of the fungus Flammulina velutipes were found to contain various
scarce fatty acids including dodec-11-enoic
acid and di- and tri-unsaturated C16 isomers. A biotechnological
approach using a heterologously expressed carboxylic acid reductase
was developed to transform the fatty acids into the respective aldehydes,
yielding inter alia dodec-11-enal. Supplementation
studies gave insights into the fungal biosynthesis of this rarely
occurring acid and suggested a terminal desaturation of lauric acid
being responsible for its formation. A systematic structure–odor
relationship assessment of terminally unsaturated aldehydes (C7–C13) revealed odor thresholds in the range
of 0.24–22 μg/L in aqueous solution and 0.039–29
ng/L in air. In both cases, non-8-enal was identified as the most
potent compound. All aldehydes exhibited green odor qualities. Short-chained
substances were additionally associated with grassy, melon-, and cucumber-like
notes, while longer-chained homologs smelled soapy and coriander leaf-like
with partly herbaceous nuances. Dodec-11-enal turned out to be of
highly pleasant scent without off-notes.