Abstract
The rapid Friedel-Crafts chromogenic acylation of alkene groups at ambient temperatures using a 25:1 mixture of 98% acetyl chloride and 70% perchloric acid is shown to have all the properties needed to serve as a potential quality control reagent that can be used to routinely discriminate among steroid analogs. Although ostensibly a non-selective reagent, from these and prior applications on terpenes and polyunsaturated acid esters, it is seen that the reaction is capable of discriminating bewteen geometric isomers and even enantiomers. The selectivity towards acylation of the α- over the β-position at C-17 makes the method adaptable to screening for anabolic steroids. Reactions at that position produce the more unusual results, including a positive color reaction for α-methyltestosterone even though there is no alkene functional group in the vicinity of C-17. For molecules with more than one alkene, concurrent acylations are independent one from the other and, in the absence of any interferences, their spectral properties are found to be additive.
PDF Article
More Like This
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures
Anisha Thayil K. N., Alejandro Muriano, J.-Pablo Salvador, Roger Galve, Maria Pilar Marco, Dobryna Zalvidea, Pablo Loza-Alvarez, Tsvi Katchalski, Eran Grinvald, Asher A. Friesem, and Silvia Soria
Opt. Express 16(17) 13315-13322 (2008)
Cited By
You do not have subscription access to this journal. Cited by links are available to subscribers only. You may subscribe either as an Optica member, or as an authorized user of your institution.
Contact your librarian or system administrator
or
Login to access Optica Member Subscription