Monoalkyl Phthalates from Normal Aliphatic Alcohols

Goggans, James F.; Copenhaver, J. E.

doi:10.1021/ja01265a094

Cited by 22 publications

(6 citation statements)

References 1 publication

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“…MEHP was synthesized from phthalic anhydride and 2-ethylhexanol as described by Goggans and Copenhaver [19]. Briefly, a mixture of phthalic anhydride and 2-ethylhexanol (1 : 1.5, v\v) was heated for 8 h at 130 mC.…”

Section: Synthesis Of Mehpmentioning

confidence: 99%

Role of oxidative stress in germ cell apoptosis induced by di(2-ethylhexyl)phthalate

Kasahara

Sato

Miyoshi

et al. 2002

Biochemical Journal

280

154

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Phthalate esters have been used extensively as plasticizers of synthetic polymers. Recent studies have revealed that these esters induce atrophy of the testis, although its pathogenesis remains unknown. The present study describes the possible involvement of oxidative stress in the pathogenesis of atrophy of the rat testis induced by di(2-ethylhexyl)phthalate (DEHP). Biochemical and immunohistochemical analysis revealed that oral administration of DEHP increased the generation of reactive oxygen species, with concomitant decrease in the concentration of glutathione and ascorbic acid in the testis, and selectively induced apoptosis of spermatocytes, thereby causing atrophy of this organ. Oxidative stress was selectively induced in germ cells, but not in Sertoli cells, treated with mono(2-ethylhexyl)phthalate (MEHP), a hydrolysed metabolite of DEHP. Furthermore, MEHP selectively induced the release of cytochrome c from mitochondria of the testis. These results indicate that oxidative stress elicited by MEHP principally injured mitochondrial function and induced the release of cytochrome c, thereby inducing apoptosis of spermatocytes and causing atrophy of the testis.

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Section: Synthesis Of Mehpmentioning

confidence: 99%

Role of oxidative stress in germ cell apoptosis induced by di(2-ethylhexyl)phthalate

Kasahara

Sato

Miyoshi

et al. 2002

Biochemical Journal

280

154

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“…The hypothesis that the Hb in RBC is deprived by restricted MAP seemed to be supported by an 10, 50, 100, 250, and 500, corresponds to 0.05, 0.27, 0.55, 1.39, and 2.75 fmol/RBC, respectively. R, alkyl residue of mono-alkyl phthalates.…”

Section: Discussionmentioning

confidence: 93%

“…Furthermore, testicular atrophy was induced by restricted mono-n-C 4-6 -alkylphthalates (C 4-6 -MAP) and mono-2-ethylhexylphthalate (C 4(6) -MAP), accompanied by depletion of SUDH. 4,8,10,16) Recently, Watanabe et al 3) suggested that the SUDH depletion was caused by a hypoxic condition [20-30% dissolved oxygen (DO)] based on in situ testis perfusion results. However, it is unclear whether the release of iron from RBC was caused by restricted MAP at lower concentrations than in in vivo conditions.…”

Section: Discussionmentioning

confidence: 99%

Testicular Toxicity of Mono-n-Butyl Phthalate and Related Phthalates on Bound Iron in Rat Red Blood Cells.

Watanabe

Shimizu

Matsumoto

et al. 2002

JOURNAL OF HEALTH SCIENCE

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It was previously reported that free iron was released from rat red blood cells in both an in vitro study with a metabolite, mono-n-butylphthalate (MBP), of di-n-butylphthalate (DBP) and an in vivo study with oral DBP, inducing rat testicular atrophy in hypoxic conditions due to MBP-induced hemoglobin deprivation. This study investigated whether mono-n-alkylphthalates (alkyl-carbon C 4 -C 6 ; MAP), which result in rat testicular damage, induce iron release from hemoglobin by incubation with rat red blood cells. Iron release was observed with C 3 -C 6 MAP incubation at lower doses and with C 1 and C 2 MAP incubation at higher doses, but not with C 7 , C 8 , and C 4(6) MAP.

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“…(109a). In preparing the higher monoalkyl phthalates heating at 110°C, for at least 0.5 hour has been thought necessary (45). In making larger quantities (0.25 to 0.5 mole) of the monoesters of phthalic and tetrahydrophthalic acids with the alcohols, butyl to octadecyl, a mixture of equivalent amounts of the anhydride and alcohol is heated, with constant shaking.…”

Section: Completing Esterificationmentioning

confidence: 99%

Esterification

Reid¹

1949

Ind. Eng. Chem.

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making of esters continues to be big business. Hundreds of millions of pounds of individual esters are turned out each year and the aggregate production runs into the billions. Business is so good that the scientific side of esterification is being neglected and there are few fundamental studies to be reported. There is need for information about esterification velocities and equilibria, in the high temperature range 200°t o 350°C ., for the acids and glycols which go into alkyds. An impartial investigation of the efficiencies of the various catalysts, which have been recommended, would be of interest. GENERAL Esterification reactions and the conditions under which they are carried out have been reviewed and the effects of unsaturation, solvents, and catalysts discussed ( 77).An intensive study has been made of the rates of alkaline hydrolysis of esters RC02R', in which R' is Me, Et,

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Monoalkyl Phthalates from Normal Aliphatic Alcohols

Cited by 22 publications

References 1 publication

Role of oxidative stress in germ cell apoptosis induced by di(2-ethylhexyl)phthalate

Role of oxidative stress in germ cell apoptosis induced by di(2-ethylhexyl)phthalate

Testicular Toxicity of Mono-n-Butyl Phthalate and Related Phthalates on Bound Iron in Rat Red Blood Cells.

Esterification

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