Disease relevance of ethyl acetoacetate

• Proteinaceous casts were found in the bladder of approximately half the male rats given 1000 mg ethyl acetoacetate/kg, and nephrocalcinosis was a common occurrence in female rats in this dose group [1].
• Ethyl acetoacetate encapsulated in gum arabic was administered in rodent diet for a minimum of 28 consecutive days to groups of 16 male and 16 female rats (Sprague-Dawley strain) at levels of approximately 100, 300 and 1000 mg/kg body weight/day [1].
• This was demonstrated by reducing ethyl acetoacetate with whole cells of an E. coli strain that overexpressed an NADPH-dependent, short-chain dehydrogenase from baker's yeast (Saccharomyces cerevisiae) [2].

Psychiatry related information on ethyl acetoacetate

• Following complete sensory deprivation or long-term stimulation with ethyl acetoacetate, the mean diameter of glomeruli was significantly reduced everywhere, except in the ventrolateral and ventromedial regions of the posterior olfactory bulb in rats reared with a single odor [3].

High impact information on ethyl acetoacetate

• It is assumed that neuronal pathways activated by ethyl acetoacetate stimulation are mainly located in the posterior part of the olfactory bulb [4].
• Carbon dioxide catalysis of the reaction of peroxynitrite with ethyl acetoacetate: an example of aliphatic nitration by peroxynitrite [5].
• However, the olfactory response to ethyl acetoacetate is significantly less in hypogonadal mice [6].
• An ontogenetic study of [14C]2-deoxyglucose (2-DG) uptake within the olfactory bulbs was performed in 1-, 4-, 7- and 21 day-old guinea-pigs exposed to a pure chemical odor, ethyl acetoacetate (EAA) [7].
• The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H(2)O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0 degrees C) [8].

Biological context of ethyl acetoacetate

• 3-Phenylpyrazolo[4,3-b]pyridines were synthesized via a cyclization of 4-amino-3-phenylpyrazoles 11-13 with ethyl acetoacetate [9].
• The administration of ethyl acetoacetate in the diet did not adversely affect the growth or general health of the animals or their food intakes [1].
• A synthetic route for A-ring aromatic steroid intermediates starting from alkylation of dianion derived from acetoacetic ester with m-methoxyphenylethyl bromide to form benzene ring connected to a linear six-carbon fragment is described [10].

Associations of ethyl acetoacetate with other chemical compounds

• A series of quinoline-based 3,5-dihydroxyheptenoic acid derivatives were synthesized from quinolinecarboxylic acid esters by homologation, aldol condensation with ethyl acetoacetate dianion, and reduction of 3-hydroxyketone to evaluate their ability to inhibit the enzyme HMG-CoA reductase in vitro [11].
• We synthesized 5,6-dehydrokawain (1) and yangonin (4) via three steps from the dianion of ethyl acetoacetate achieving a good yield and determined their conformations by high resolution NMR and x-ray crystallographic analysis [12].

References