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Chemical Compound Review:

SureCN239230 2-ethoxyoxolane

Synonyms: AG-D-70072, KB-23680, AKOS015915920, FT-0636892, AC1L29RC, ...

Wong, H.L. et al., Hecht, S.S. et al., Wang, M. et al., Wong, H.L. et al., Hecker, L.I. et al.

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High impact information on EINECS 236-569-9

One product of metabolism of NO-PYR is 2-hydroxytetrahydrofuran formed by alpha-hydroxylation by the microsomes [1].
It was identified by comparison of its UV spectrum and retention time to those of a standard, by conversion upon NaBH4 treatment to N2-(4-hydroxybutyl)deoxyguanosine, and by neutral thermal hydrolysis to 2-hydroxytetrahydrofuran (THF-OH) [2].
Metabolic alpha-hydroxylation of nitrosopyrrolidine, which is thought to be the critical step in activation of this compound, was demonstrated by detection in vitro and in vivo of 2-hydroxytetrahydrofuran, which was the product of decomposition of alpha-hydroxynitrosopyrrolidine [3].

Analytical, diagnostic and therapeutic context of EINECS 236-569-9

The major alpha-hydroxylation products of NPIP and NPYR, 2-hydroxytetrahydro-2H-pyran (2-OH-THP) and 2-hydroxytetrahydrofuran (2-OH-THF), respectively, were monitored by high performance liquid chromatography with radioflow detection [4].
To compare alpha-hydroxylation rates of the two nitrosamines, tritiated 2-hydroxytetrahydro-2H-pyran and 2-hydroxy-5-methyltetrahydrofuran, the major NPIP alpha-hydroxylation products, and tritiated 2-hydroxytetrahydrofuran, the major NPYR alpha-hydroxylation product, were quantitated by HPLC with UV absorbance and radioflow detection [5].

References

Metabolism of the liver carcinogen N-nitrosopyrrolidine by rat liver microsomes. Hecker, L.I., Farrelly, J.G., Smith, J.H., Saavedra, J.E., Lyon, P.A. Cancer Res. (1979) [Pubmed]
Formation of N2-tetrahydrofuranyl and N2-tetrahydropyranyl adducts in the reactions of alpha-acetoxy-N-nitrosopyrrolidine and alpha-acetoxy-N-nitrosopiperidine with DNA. Wang, M., Young-Sciame, R., Chung, F.L., Hecht, S.S. Chem. Res. Toxicol. (1995) [Pubmed]
Chemical studies on tobacco smoke LVI. Tobacco specific nitrosamines: origins, carcinogenicity and metabolism. Hecht, S.S., Chen, C.B., Ornaf, R.M., Hoffmann, D., Tso, T.C. IARC scientific publications. (1978) [Pubmed]
Comparative metabolism of N-nitrosopiperidine and N-nitrosopyrrolidine by rat liver and esophageal microsomes and cytochrome P450 2A3. Wong, H.L., Murphy, S.E., Wang, M., Hecht, S.S. Carcinogenesis (2003) [Pubmed]
Preferential metabolic activation of N-nitrosopiperidine as compared to its structural homologue N-nitrosopyrrolidine by rat nasal mucosal microsomes. Wong, H.L., Murphy, S.E., Hecht, S.S. Chem. Res. Toxicol. (2003) [Pubmed]

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