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A synthesis of 4‐hydroxy‐2‐ trans ‐nonenal and 4‐( 3 H) 4‐hydroxy‐2‐ trans ‐nonenal
Author(s) -
Chandra Animesh,
Srivastava Satish K.
Publication year - 1997
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-997-0100-6
Subject(s) - chemistry , acetal , aldehyde , oxidizing agent , hydrolysis , sodium methoxide , pyridinium , catalysis , organic chemistry , pyridinium chlorochromate , derivative (finance) , medicinal chemistry , financial economics , economics
4‐Hydroxy‐2‐ trans ‐nonenal, the most abundant and toxic unsaturated aldehyde generated during membrane lipid peroxidation, was synthesized starting from fumaraldehyde dimethyl acetal. In the first step of the synthesis, the fumaraldehyde dimethyl acetal was partially hydrolyzed using amberlyst catalyst to obtain the monoacetal. The 4‐hydroxy‐2‐ trans ‐nonenal was synthesized by the Grignard reaction of the fumaraldehyde monoacetal with 1‐bromopentane. 4‐Hydroxy‐2‐ trans ‐nonenal, obtained as its dimethylacetal, was oxidized to its corresponding 4‐keto derivative using pyridinium chlorochromate buffered with sodium acetate as the oxidizing agent. 4‐( 3 H) 4‐Hydroxy‐2‐ trans ‐nonenal was obtained in one step by the sodium borotriteride reduction of the 4‐keto derivative.