Studies on the Toxicity of Glycidaldehyde

Ch, Hine; Rj, Guzman; Mk, Dunlap; Lima, Rita de Cássia Gonçalves de; Gs, Loquvam

doi:10.1080/00039896.1961.10662813

Cited by 8 publications

(2 citation statements)

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“…The availability of reference standards from these studies enabled us to show that adenine rather than guanine is the principal site of attack of glycidaldehyde toward mouse skin DNA in vivo (23). It is probable, however, that deoxyguanosine adducts could be formed as minor adducts at levels lower than the detection limits in those studies (i.e., less than 1 adduct in 10 7 -10 8 nucleotides). During our studies of glycidaldehyde-guanosine adducts, we discovered that formaldehyde is released from the major adduct, and this leads to the additional formation of a formaldehyde-guanosine adduct (for a preliminary account, see ref 24).…”

Section: Introductionmentioning

confidence: 88%

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Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine

Golding

Slaich

Kennedy

et al. 1996

Chem. Res. Toxicol.

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Convenient synthesis of rac-glycidaldehyde from rac-but-3-ene-1,2-diol and (R)-glycidaldehyde from D-mannitol are described. (R)-Glycidaldehyde (1) reacts with guanosine in water (pH 4-11, faster reaction at higher pH) to give initially 6(S)-hydroxy-7(S)-(hydroxymethyl)-3-(beta-D-ribofuranosyl)-5,6,7- trihydroimidazo[1,2-alpha]purin-9(3H)-one (7a) and 6(S),7(R)-dihydroxy-3-(beta-D-ribofuranosyl)-5,6,7,8- tetrahydropyrimido[1,2- alpha]purin-10(3H)-one (8a). The former decomposes to 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(beta-D-ribofuranosyl)imidazo[1,2- alpha]purine (3a), 5,9-dihydro-9-oxo-3-(beta-D-ribofuranosyl)imidazo[1,2-alpha]purine (5a, 1,N2-ethenoguanosine), and formaldehyde, while the latter adduct is relatively stable. The position of the hydroxymethyl group on the imidazo ring of 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(beta-D-ribofuranosyl)imidazo-[1,2 - alpha]purine was proved by 13C NMR analysis of adducts derived from [1-15N]guanosine and [amino-15N]guanosine. At longer reaction times, the adduct 7,7'-methylenebis[5,9-dihydro-9-oxo-3-(beta-D-ribofuranosyl)imidazo[1,2- alpha]purine (4a) is formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by 13C NMR analysis of the 15N-labeled adduct derived from [1-15N]guanosine. Analogous adducts were obtained from the reaction between glycidaldehyde and deoxyguanosine. Mechanisms of formation of the adducts from glycidaldehyde and guanosine/deoxyguanosine are proposed and supported by model studies with simple amines. The formaldehyde produced in the reactions described reacts with guanosine to give the known adduct N2-(hydroxymethyl)guanosine (9).

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Section: Introductionmentioning

confidence: 88%

“…Due to its reactivity, attention was focused on the adverse toxicology of the compound. In vitro tests (4), long-term animal carcinogenicity studies (5,6), and inhalation studies in humans (7) were carried out. Glycidaldehyde was classified as an animal carcinogen on the basis of these studies (8,9).…”

Section: Introductionmentioning

confidence: 99%

Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine

Golding

Slaich

Kennedy

et al. 1996

Chem. Res. Toxicol.

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Glycidyl Ethers (Aliphatic Glycidyl Ethers, Aromatic Monoglycidyl Ethers, Aromatic Diglycidyl Ethers, Polyglycidyl Ethers) and Precursor Epoxy Compounds

Jean,

Pottenger,

Mattke

et al. 2023

Patty's Toxicology

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This chapter updates the hazard information of glycidyl ether epoxy compounds frequently encountered in industrial manufacture of epoxy resins as an important reference for Industrial Hygienists and other industry health and safety professionals. The chapter covers basic general information, including chemical/physical properties, production and uses, and a review of available toxicology data for 20 of these substances. There have been significant additions to the health and safety information available for these glycidyl ether substances since the previous publication of this chapter. This includes filling data gaps for the most basic of hazard characterizations as well as important studies evaluating the potential for in vivo genotoxicity and reproductive/developmental toxicity. The advancements in our understanding of the hazard potential are substance‐specific and growing as there are significant studies ongoing at the time of this publication. The information provided in this chapter represents our understanding of the most up‐to‐date information for each substance.

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Glycidaldehyde 765‐34‐4

2004

Sax's Dangerous Properties of Industrial Materials

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Studies on the Toxicity of Glycidaldehyde

Cited by 8 publications

References 1 publication

Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine

Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine

Glycidyl Ethers (Aliphatic Glycidyl Ethers, Aromatic Monoglycidyl Ethers, Aromatic Diglycidyl Ethers, Polyglycidyl Ethers) and Precursor Epoxy Compounds

Glycidaldehyde 765‐34‐4

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