Photodegradation of Hexachlorophene and Related Polychlorinated Phenols

Shaffer, Gary W.; Nikawitz, E.; Manowitz, Milton; Daeniker, H. U.

doi:10.1111/j.1751-1097.1971.tb06122.x

Cited by 11 publications

(6 citation statements)

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“…HCP was removed from the thin-layer plates as soon as possible because it discolored to a brownish oil when exposed to light. Shaffer et al (1971) reported a similar degradation of HCP when it was exposed to UV light.…”

Section: Methodsmentioning

confidence: 81%

Metabolism of hexachlorophene in the rabbit. Excretion, tissue distribution, and characterization of the urinary glucuronide conjugate

Gandolfi¹,

Buhler²

1977

J. Agric. Food Chem.

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Section: Methodsmentioning

confidence: 81%

Metabolism of hexachlorophene in the rabbit. Excretion, tissue distribution, and characterization of the urinary glucuronide conjugate

Gandolfi¹,

Buhler²

1977

J. Agric. Food Chem.

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“…The formation of aryl radicals during the photodehalogenation of polyhalogenated phenols has long been postulated or implicated (Horio, 1984;Johnson, 1984;O'Quinn et al, 1967). Compounds which are structurally related to BT and FT, for example hexachlorophene (Shaffer et al, 1971), TCSA, TBS (Coxon et al, 1965) and Jadit (Jung et al, 1968), all yield dehalogenated products upon UV photolysis. In most of these dehalogenations there is supporting evidence for the involvement of free radicals (Kochevar, 1979).…”

Section: Discussionmentioning

confidence: 99%

SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS–XII. SPIN TRAPPING STUDY OF THE FREE RADICALS GENERATED DURING THE PHOTOLYSIS OF PHOTO ALLERGENS BITHIONOL and FENTICHLOR

Chignell

1987

Photochem & Photobiology

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Free radicals were trapped and observed by ESR when photoallergens bithionol and fentichlor were irradiated in the presence of spin traps N‐t‐butyl‐α‐phenylnitrone (PBN) and 5,5‐dimethyl‐pyrroline‐N‐oxide (DMPO). In the absence of air, both PBN and DMPO trapped a carbon‐centered radical. The carbon‐centered radical, which was capable of abstracting a hydrogen atom from cysteine, glutathione, ethanol and formate, was identified as an aryl radical derived from the homolytic cleavage of the carbon‐chlorine bond. In the presence of air, both carbon‐centered radicals and hydroxyl radicals were trapped by DMPO. Under similar conditions, the yield of the hydroxyl radicals was greater from bithionol than from fentichlor. The presence of the hydroxyl radical was confirmed by kinetic experiments employing hydroxyl radical scavengers (ethanol, formate). Superoxide and H2O2 were not involved. Experiments with oxygen‐17O indicated that the hydroxyl radicals came exclusively from dissolved oxygen. The precursor of the hydroxyl radical is postulated to be a peroxy intermediate (ArOO*) derived from the reaction of an aryl radical (Ar*) with molecular oxygen. Both bithionol and fentichlor photoionized only when excited in the UVC (<270 nm) region. Free radicals have long been postulated in the photodechlorination of bithionol and fentichlor and the present study provides supporting evidence for such a mechanism. Aryl and hydroxyl radicals are reactive chemical species which may trigger a series of events that culminate in photoallergy.

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“…Gutenmann and Lisk (1970), Noori (personal communication), Duggan (1974), Johnston and Porcaro (1964), and Van Auken and Hulse (1977a,b, 1978 reported methods for extracting and quantitating HCP from plant tissues. In a very important related paper, Shaffer et al (1971) determined some of the UV-photodegradation products of HCP and related polychlorinated phenols. There are no reports available concerning metabolism, fate, ecological significance, or environmental degradation of HCP.…”

Section: Discussionmentioning

confidence: 99%

“…HCP absorbs UV radiation (Shaffer et al 1971) and the most likely method of decomposition of this molecule would be photolysis. Shaffer et al (1971) showed that UV photolysis of HCP does occur, but they carried out their studies of photodegradation in the absence of Oj and HjO. The experiments reported here were carried out in air, in the presence of both O^ and water vapor, so oxidation or hydrolysis of the HCP could not be ruled out.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Translocation and Metabolism of Leaf Applied Hexachlorophene in Peanuts

Auken

Hulse

1978

Physiologia Plantarum

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Translocation, distribution, metabolism and photolysis of hexachlorophene (HCP) were investigated in peanut plants (Arachis hypogea L., Spanish type) grown under standardized conditions and treated with l4C‐ring‐labeled HCP. Treatment time ranged from 0–114 days. Autoradiographic analyses were performed on all plants. Selected plant tissues were extracted and chromatographed, using both thin layer and gas liquid chromatography. No translocation of HCP was detected in the plant tissue. No HCP metabolites were found. Some HCP was lost from the leaves and inert controls at a specific rate per unit time. The rates were slightly different, being slower on the leaves than on the controls. At the end of the 114‐day treatment and based on regression analysis of thin layer chromatographic plates, an average of 68% of the applied HCP remained unaltered on the treated plants and an average of 77% remained on the controls. This indicated that, respectively, 32 and 23% of the original HCP had been altered. This 9% difference was statistically significant. Upon further analyses of the above data, using gas chromatographic methods, as many as 14 peaks were found in the treated samples and the controls, including some parent material. Ultraviolet photolysis seems to be the mechanism responsible for alteration of the HCP on the treated plants and controls. Two photolysis products have been identified by gas liquid chromatography‐mass spectral analysis. Twelve other electrophylic compounds have been found in various treated plant or control extracts. Further analyses will be necessary to verify the identification and quantification of the other degradation products.

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Photodegradation of Hexachlorophene and Related Polychlorinated Phenols

Cited by 11 publications

References 1 publication

Metabolism of hexachlorophene in the rabbit. Excretion, tissue distribution, and characterization of the urinary glucuronide conjugate

Metabolism of hexachlorophene in the rabbit. Excretion, tissue distribution, and characterization of the urinary glucuronide conjugate

SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS–XII. SPIN TRAPPING STUDY OF THE FREE RADICALS GENERATED DURING THE PHOTOLYSIS OF PHOTO ALLERGENS BITHIONOL and FENTICHLOR

Translocation and Metabolism of Leaf Applied Hexachlorophene in Peanuts

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