92168-98-4Relevant articles and documents
Biotechnological Production of Odor-Active Methyl-Branched Aldehydes by a Novel α-Dioxygenase from Crocosphaera subtropica
Albrecht, Florian,Buchhaupt, Markus,Fraatz, Marco A.,Geissler, Torsten,Hahne, Friederike,Hammer, Andreas K.,Jordan, Paulina,Ley, Jakob,Schrader, Jens,Zorn, Holger
, p. 10432 - 10440 (2020/10/26)
As a result of their pleasant odor qualities and low odor thresholds, iso-and anteiso-fatty aldehydes represent promising candidates for applications in flavoring preparations. A novel cyanobacterial α-dioxygenase from Crocosphaera subtropica was heterologously expressed in Escherichia coli and applied for the biotechnological production of C12-C15 branched-chain fatty aldehydes. The enzyme has a sequence identity of less than 40% to well-investigated α-dioxygenase from rice. Contrary to the latter, it efficiently transformed short-chained fatty acids. The kinetic parameters of α-dioxygenase toward unbranched and iso-branched-chain substrates were studied by means of an oxygen-depletion assay. The transformation products (C12-C15 iso-and anteiso-aldehydes) were extensively characterized, including their sensory properties. The aldehydes exhibited green-soapy, sweety odors with partial citrus-like, metallic, peppery, and savory-tallowy nuances. Moreover, the two C14 isomers showed particularly low odor threshold values of 0.2 and 0.3 ng/L in air as determined by means of gas chromatography-olfactometry.
Identification and total synthesis of novel fatty acids from the siphonarid limpet Siphonaria denticulata
Carballeira,Cruz,Hill,De Voss,Garson
, p. 1426 - 1429 (2007/10/03)
The novel fatty acids 17-methyl-6(Z)-octadecenoic acid and 17-methyl-7(Z)-octadecenoic acid were identified for the first time in nature in the mollusk Siphonaria denticulata from Queensland, Australia. The principal fatty acids in the limpet were hexadecanoic acid, octadecanoic acid, and (Z)-9-octadecenoic acid, while the most interesting series of monounsaturated fatty acids was a family of five nonadecenoic acids with double bonds at either Δ7, Δ9, Δ12, or Δ13. The novel compounds were characterized using a combination of GC-MS and chemical transformations, such as dimethyl disulfide derivatization. The first total syntheses for the two novel methyl-branched nonadecenoic acids are also described, and these were accomplished in four to five steps and in high yields.
