Chemistry of muconaldehydes of possible relevance to the toxicology of benzene

Journal Article · Sun Dec 01 04:00:00 EST 1996 · Environmental Health Perspectives

DOI:https://doi.org/10.1289/ehp.961041201· OSTI ID:472161

Bleasdale, C; Kennedy, G; MacGregor, J O ^[1]

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1. Univ. of Newcastle upon Tyne (United Kingdom); and others

(ZZ)-Muconaidehyde reacted with primary amines to give N-substituted-2-(2{prime}-oxoethyl)-pyrroles, which were reduced to 4substituted-2-(2{prime}-hydroxyethyl)-pyrroles by sodium borohydride. The pyrrole-forming reaction is exhibited by valine and its methyl ester, and is being developed with terminal valine in hemoglobin as a means of dose monitoring (ZZ)-muconaldehyde, a putative metabolite of benzene. Reactions in aqueous solution between (ZZ)-muconaldehyde and adenosine, deoxyadenosine, guanosine, or deoxyguanosine leading to pyrrole-containing adducts are described. The elucidation of the structures of the adducts was assisted by the study of reactions between (ZZ)-muconaldehyde and both nucleoside derivatives and a model compound for guanosine. Reactions of (ZZ)-muconaldehyde are complicated by its isomerization to (EZ)- and (EE)-muconaldehyde. The kinetics of this process have been studied in benzene, acetonitrile, and dimethylsulfoxide. 17 refs., 1 tab.

• Sponsoring Organization: USDOE
• OSTI ID: 472161
• Report Number(s): CONF-9506288--
• Journal Information: Environmental Health Perspectives, Journal Name: Environmental Health Perspectives Journal Issue: Suppl.6 Vol. 104; ISSN EVHPAZ; ISSN 0091-6765
• Country of Publication: United States
• Language: English

Related Subjects

02 PETROLEUM
55 BIOLOGY AND MEDICINE
BASIC STUDIES
56 BIOLOGY AND MEDICINE
APPLIED STUDIES
ACETONITRILE
ADENOSINE
AIR POLLUTION
ALDEHYDES
AMINES
BENZENE
BIOLOGICAL EFFECTS
BONE MARROW
EXHAUST GASES
GLUTATHIONE
GUANOSINE
HEMOGLOBIN
ISOMERS
METABOLISM
MICE
OCCUPATIONAL EXPOSURE
OXIDATION
PETROLEUM REFINERIES
TOXICITY