Identification of several Tonalide (R) transformation products in the environment

Organic synthesis combined with trace-analytical methods has been applied to detect potential Tonalide (AHTN) transformation products in a semi-quantitative way in environmental samples by using a well-established trace-analytical method, developed for the quantification of the parent compound AHTN. For the first time, indications for the presence of transformation products of the synthetic musk compound 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone (1) (Tonalide®, AHTN) have been found in the environment. Pure standards of the detected products were obtained by multistep syntheses from Tonalide®. Two main derivatives, 3-acetyl-5,6,7,8-tetrahydro-5,5,7,8,8-pentamethyl-2-naphthalenecarbaldehyde (2) and (3-ethyl-5,6,7,8-tetrahydro-5,5,7,8,8-pentamethyl-2-naphthalenyl)methanol (4), and three minor products, (5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphtalenyl)methanol (6), 5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphtalenecarbaldehyde (7), and methyl 5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenecarboxylate (8), were identified in three human breast-milk samples and three fish samples. All samples contained one or several of these transformation products at a concentration range of around 10 pg/g wet weight.