Oxidative Metabolism of Heterocyclic Ring Systems

Damani, L. A.; Crooks, Peter A.

doi:10.1016/b978-0-12-380060-2.50010-6

Cited by 19 publications

(17 citation statements)

References 42 publications

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“…The supporting substance pyrazine ] is a weak base with a pK a = 0.6 (Damani & Crooks, 1982). At intestinal pH (pH = 5 -7), absorption of weak amine bases such as pyrazine is optimal, because at these pHs such substances occur largely in the non-ionised state, which facilitates their absorption through the gastro-intestinal membranes (Hogben et al, 1959;Schranker et al, 1957).…”

Section: Iii2 Absorption Distribution and Eliminationmentioning

confidence: 99%

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24

Flavourings¹

2011

EFS2

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The remaining 18 substances were evaluated through a stepwise approach that integrates information on structure-activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. The Panel concluded that 17 substances 14.083, 14.084, 14.086, 14.087, 14.091, 14.097, 14.099, 14.101, 14.102, 14.108, 14.113, 14.122, 14.127, 14.129, 14.148, and 14.161] do not give rise to safety concerns at their levels of dietary intake, estimated on the basis of the MSDI approach. For the remaining substance .052] additional toxicity data are required. Besides the safety assessment of these flavouring substances, the specifications for the materials of commerce have also been considered and for two substances information on specifications is lacking.

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Section: Iii2 Absorption Distribution and Eliminationmentioning

confidence: 99%

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24

Flavourings¹

2011

EFS2

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“…Further oxidation of the acetyl group on 2-acetyl-5-methylpyrrole is also expected. According to (Damani and Crooks, 1982) pyrroles are likely substrates for elecrophilic enzymatic oxidation at N-1.…”

Section: Iii4 Summary On Metabolismmentioning

confidence: 99%

Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28

Flavourings¹

2013

EFS2

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to evaluate 24 flavouring substances in the Flavouring Group Evaluation 24, Revision 2, using the Procedure in Commission Regulation (EC) No 1565/2000. This revision was made required owing to the inclusion of the assessment of new toxicity data on one supporting substance, 2-acetylpyrrole , to support the re-evaluation of one candidate substance, 2-acetyl-5-methylpyrrole ]. Nine of the original 33 candidate substances 14.002, 14.023, 14.094, 14.107, 14.138, 14.145, 14.163 and 14.169], for which additional data were requested, are no longer supported by Industry for use as flavouring substances in Europe and will therefore not be considered any further. None of the 24 substances were considered to have genotoxic potential. These candidate substances were evaluated through a stepwise approach that integrates information on the structure-activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. The Panel concluded that the 24 substances 14.088, 14.089, 14.092, 14.093, 14.103, 14.104, 14.105, 14.106, 14.110, 14.115, 14.116, 14.117, 14.118, 14.120, 14.124, 14.125, 14.131, 14.134, 14.135, 14.136, 14.140, 14.143 and 14.150] do not give rise to safety concern at their levels of dietary intake, estimated on the basis of the MSDI approach. Besides the safety assessment of these flavouring substances, the specifications for the materials of commerce have also been considered. Adequate specifications including complete purity criteria and identity for the materials of commerce have been provided for all 24 candidate substances. Since the publication of the previous version of FGE.24, FGE.24Rev1, nine of the original 33 candidate substances 14.002, 14.023, 14.094, 14.107, 14.138, 14.145, 14.163 and 14.169], for which additional data were required, are no longer supported by Industry for use as flavouring substances in Europe and will therefore not be considered any further. This revision of FGE.24, FGE.24Rev2, therefore deals only with 24 candidate substances.None of the 24 candidate substances can exist as geometrical or optical isomers.Twenty-two of the candidate substances are classified into structural class II and two are classified into structural class III.Twenty-one candidate substances in the present group have been reported to occur naturally in a wide range of food items.In its evaluation, the Panel as a default used the "Maximised Survey-derived Daily Intake" (MSDI) approach to estimate the per capita intakes of the flavouring substances in Europe. However, when the Panel examined the information provided by the European Flavour Industry on the use levels in various foods, it appeared obvious that the MSDI approach in a number of cases would grossly underestimate the intake by regular consumers of products flavoured at the use level reported by the Industry, especially in those cases where the an...

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“…3-Hydroxyindole (indoxyl), resulting from electrophilic attack at C-3, is the main metabolite of indole in various species. Minor metabolites are oxindole and 5-hydroxyoxindole, resulting from hydroxylation at C-2 and subsequent C-5 hydroxylation (Damani and Crooks, 1982). The metabolism of [2][3][4][5][6][7][8][9][10][11][12][13][14] C]-indole was investigated by King et al (1966).…”

Section: Metabolismmentioning

confidence: 99%

Safety and efficacy of pyridine and pyrrole derivatives belonging to chemical group 28 when used as flavourings for all animal species

Additives¹,

Högstrand²

2016

EFS2

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Following a request from the European Commission, the EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific opinion on the safety and efficacy of nine compounds belonging to chemical group 28 (pyridine, pyrrole and quinoline derivatives). They are currently authorised as flavours in food. The FEEDAP Panel concludes that piperine, 3-methylindole, indole, 2-acetylpyridine and 2-acetylpyrrole are safe at the proposed maximum use level of 0.5 mg/kg complete feed for all animal species; trimethyloxazole, 3-ethylpyridine, pyrrolidine and 2,6-dimethylpyridine are safe at the proposed use level of 0.5 mg/kg complete feed for cattle, salmonids and non-food-producing animals, and at the use level of 0.3 mg/kg complete feed for pigs and poultry. No safety concern would arise for the consumer from the use of these compounds up to the highest safe level in feeds. Hazards for skin and eye contact, and respiratory exposure are recognised for the majority of the compounds under application. Most are classified as irritating to the respiratory system. The concentrations considered safe for the target species are unlikely to have detrimental effects on the terrestrial and fresh water environments. As all the compounds under assessment are used in food as flavourings, and their function in feed is essentially the same as that in food, no further demonstration of efficacy is necessary. In the absence of data on the stability in water for drinking, the FEEDAP Panel is unable to conclude on the safety or efficacy of the substances under this mode of delivery.

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Oxidative Metabolism of Heterocyclic Ring Systems

Cited by 19 publications

References 42 publications

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24

Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28

Safety and efficacy of pyridine and pyrrole derivatives belonging to chemical group 28 when used as flavourings for all animal species

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