Synthesis of 13 C-labelled ω-hydroxy carboxylic acids of the general formula HO213 C-(CH2 )n -CH2 OH or HO2 C-(CH2 )n -13 CH2 OH (n = 12, 16, 20, 28)

Abstract

¹³ C-labelled ω-hydroxy-carboxylic acids HO₂¹³ C-(CH₂ )_n -CH₂ OH or HO₂ C-(CH₂ )_n -¹³ CH₂ OH (n = 12, 16, 20, 28) with ¹³ C labels selectively introduced either at the carboxy group or at the primary alcohol function at the end of the hydrocarbon chain have been synthesized. Different synthetic strategies had to be applied depending on the position of the label, the chain length of the respective synthetic target and due to economic considerations. ¹³ C labels in general were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding labelled carboxy functions, which may also be reduced to give the labelled primary alcohol group. All new compounds are characterized by GC/MS, IR and NMR methods as well as by elemental analysis.

Keywords: 13C labelling; cutin; fatty acids; suberin; ω-hydroxy-carboxylic acids.