Phthalate esters: Occurrence and biological effects

  • David B. Peakall
Part of the Residue Reviews book series (RECT, volume 54)

Abstract

This review considers the occurrence and biological activity of phthalates. The analytical procedures and problems have been reviewed by Fishbein and Albro (1972). Source documents of especial value were the National Institutes of Environmental Health Sciences Symposium (third issue of Environmental Health Perspectives, January 1973), Society of Plastic Engineers Symposium (March 1973), and the Toxicology Information Response Center Report (Autian 1972 and 1973). Many articles in Russian and other eastern European languages have been obtained through the U.S.-U.S.S.R. Health Exchange Program under the sponsorship of the National Institutes of Environmental Health Sciences; these articles are considered in more detail as they are not readily available to many scientists

Keywords

Toxicity Toxicology Eucalyptus Incineration Arthrobacter 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Aebi, A., J. Asselineau, and E. Lederer: Sur les lipides de la souche humaine “Brévannes” de Mycobacterium tuberculosis. Bull. Soc. Chim. Biol. 35, 661 (1953).PubMedGoogle Scholar
  2. Albro, P. W., R. Thomas, and L. Fishbein: Metabolism of diethylhexyl phthalate by rats. Isolation and characterization of the urinary metabolites. J. Chromatogr. 76, 321 (1973).PubMedGoogle Scholar
  3. American Conference of Government Industrial Hygienists: Theshold limit values of airborne contaminants for 1972. Cincinnati (1972).Google Scholar
  4. Aso, K., M. Migata, and M. Tomoda: On the production of phthalic acid by Azotobacter. Proc. 2nd Internat. Congress Soil Sci. 3, 40 (1932).Google Scholar
  5. Asselineau, J.: Sur la composition des lipides de Corynebacterium diphtheriae. Biochim. Biophys. Acta 54, 359 (1961).PubMedGoogle Scholar
  6. Autian, J.: Toxicity and health threats of phthalate esters: Review of the literature. Toxicology Information Response Center (1972).Google Scholar
  7. - Toxicity and health threats of phthalate esters: Review of the literature. Environ. Health Perspect. 4, 3 (1973).PubMedGoogle Scholar
  8. Baroche, C.: Actions tératogène et mutagène du phtalate acide de potassium chez la Drosophile. Bull. Cancer 52, 241 (1965).Google Scholar
  9. - Actions de la thalidomide chez la Drosophile: Développement et tumorigenese. Comparaison avec le phtalate de potassium et quelques composes non phtaliques. Bull. Cancer 55, 413 (1968).PubMedGoogle Scholar
  10. Batta, A. K., and S. Rangaswami: Chemical constituents of Polyporus dryadeus var. brevisporus and Fomes allardii. Phytochem. 8, 1309 (1969).Google Scholar
  11. Bauman, J., R. E. Cameron, G. Kritchevsky, and G. Rouser: Detection of phthalate esters as contaminants of lipid extracts from soil samples stored in standard soil bags. Lipids 2, 85 (1967).PubMedGoogle Scholar
  12. Berk, S., H. Ebert, and L. Teitell: Utilization of plasticizers and related organic compounds by fungi. Ind. Eng. Chem. 49, 1115 (1957).Google Scholar
  13. Beroza, M., B. A. Bdskl, and J. M. Ruth: Di-(2-ethylhexyl) phthalate in thermally oxidized corn oil. J. Amer. Oil Chem. Soc. 45, 441 (1968).Google Scholar
  14. Blickensdorfer, P., and L. Templeton: A study of the toxic properties of diethyl phthalate. J. Am. Pharm. Assoc. 19, 1179 (1930).Google Scholar
  15. Bohrmann, H., E. Stahl, and H. Mitsuhashi: Studies of the constituents of Umbelliferae plants. 8. Chromatographic studies on the constituents of Cnidium officinale Makino. Chem. Pharm. Bull. 15, 1606, (1967).PubMedGoogle Scholar
  16. Bourne, H. G., H. T. Yee, and Seferian: The toxicity of rubber additives: Findings from a survey of 140 plants in Ohio. Arch. Environ. Health 16, 700 (1968).PubMedGoogle Scholar
  17. Bower, R. K., S. Haberman, and P. D. Minton: Teratogenic effects in the chick embryo caused by esters of phthalic acid. J. Pharmacol. Exp. Ther. 171, 314 (1970).PubMedGoogle Scholar
  18. Braun, B., and H. J. Kümmel: Uber die Verwendungsmöglichkeit von Kunststoffbehaltern zur Aufbewährung von Blut und Infusionslösungen. Dtsch. Apoth-Ztg. 103, 467 (1963).Google Scholar
  19. Breger, I. A.: Geochemistry of lipids. J. Amer. Oil Chem. Soc. 43, 197 (1966).Google Scholar
  20. - Phthalates in oil. Chem. Eng. News, p. 19, Jan. 17 (1972).Google Scholar
  21. Brewer, N. R., A. J. Carlson, and A. Pratt: Chronic toxicity studies on alkyl phenyl phthalate. Food Research 20, 531 (1955).Google Scholar
  22. Brown, V. K., C. M. Muir, and E. Thorpe: A contribution to the toxicology of some alcohol mixtures containing 7 to 9 and 9 to 11 carbon atoms and the corresponding phthalate esters. Arch. Toxik. 26, 84 (1970).PubMedGoogle Scholar
  23. Calley, D., J. Autian, and W. L. Guess: Toxicology of a series of phthalate esters. J. Pharm. Sci. 55, 158 (1966).PubMedGoogle Scholar
  24. Carpenter, E. J., and K. L. Smith, Jr.: Plastics on the Sargasso Sea surface. Science 175, 1240 (1972).PubMedGoogle Scholar
  25. Cerbulis, J., and J. S. Ard: Method for isolation and detection of dioctyl phthalate from milk lipids. J. Assoc. Official Anal. Chemists 50, 646 (1967).Google Scholar
  26. Chambon, P., M. Riotte, M. Dauden, R. Chambon-Mougenot, and J. Bringuier: Etude du metabolisme des phtalates de dibutyle et de diethyle chez le rat. C. R. Acad. Sc. Paris 273, 2165 (1971).Google Scholar
  27. Cifrulak, S. D.: Spectroscopic evidence of phthalates in soil organic matter. Soil Sci. 107, 63 (1969).Google Scholar
  28. Corcoran, E. F.: Gas-chromatographic detection of phthalic acid esters. Environ. Health Perspect. 3, 13 (1973).PubMedGoogle Scholar
  29. Covello, M., C. Ranaudo, and O. Schettino: Determination of organic phthalates in oils. Rass. Chim. 19, 236 (1967).Google Scholar
  30. Cross, B. E., R. H. B. Galt, J. R. Hanson, P. J. Curtis, J. F. Grove, and A. Morrison: New metabolites of Gibberella fujikuroi. II. The isolation of fourteen new metabolites. J. Chem. Soc., pp. 2937–2943 (1963).Google Scholar
  31. Decoste, J. B.: Soil burial resistance of vinyl chloride plastics. Ind. Eng. Chem. 7, 238 (1968).Google Scholar
  32. Dhingra, S. N., D. R. Dhingra, and G. N. Gupta: Essential oil of kewda. Perfumery Essent. Oil Record 95, 219 (1954).Google Scholar
  33. Dillingham, E. O., and J. Autian: Teratogenicity, mutagenicity, and cellular toxicity of phthalate esters. Environ. Health Perspect. 3, 81 (1972).Google Scholar
  34. Draize, J. H., E. Alvarek, M. F. Whitesell, G. Woodard, E. C. Hagen, and A. A. Nelson: Toxicological investigations of compounds proposed for use as insect repellents. J. Pharmacol. Exp. Ther. 93, 26 (1948).PubMedGoogle Scholar
  35. Dueva, L. A., and M. V. Aldyreva: Eksperimental’naia otsenka sensibiliziruiushchego i razdrazhaiushchego kozhu deistviia ftalatnykh plastifikatorov. Gig. Tr. Prof. Zabol. 13, 17 (1969).PubMedGoogle Scholar
  36. Duke, H. N., and J. R. Vane: An adverse effect of polyvinylchloride tubing used in extracorporeal circulation. Lancet 2, 21 (1968).PubMedGoogle Scholar
  37. Dvoskin, I. A. G., N. A. Rakhmanina, F. V. Dem’Ianko, T. A. Men’shikova, L. F. Erofeeva, and A. V. Lashkina: Hygienic assessment of certain polymers (povinols). [Translated title] Gig. Sanit. 34, 7 (1969).PubMedGoogle Scholar
  38. Elizarova, O. N.: Comparative toxicologic characteristics of some plasticizers. [Translated title] Mosk. Nauchn.-Issled. Inst. Gigieny No. 9, 105 (1961).Google Scholar
  39. Etemadi, A. H.: On the origin of butyl phthalate in bacterial lipid extracts. Bull. Soc. Chim. Biol. 45, 631 (1963).Google Scholar
  40. Fassett, D. W.: Organic esters. In F. A. Patty (ed.): Industrial hygiene and toxicology, vol. 2, pp. 1902–1911. New York: Interscience (1967).Google Scholar
  41. Fishbein, L., and P. W. Albro: Chromatographic and biological aspects of the phthalate esters. J. Chromatogr. 70, 365 (1972).PubMedGoogle Scholar
  42. Frank, O., H. Baker, S. H. Hutner, and H. Sobotka: Toxicity to protozoa of thalidomide breakdown products—counteraction by nicotinic acid and glutamine. Proc. Soc. Exp. Biol. Med. 114, 326 (1963).PubMedGoogle Scholar
  43. Gaunt, I. F., J. Cooley, P. Grasso, A. B. Lansdown, and S. D. Gangolli: Acute (rat and mouse) and short-term (rat) toxicity studies on dialkyl 79 phthalate. Food Cosmetic Toxicol. 6, 609 (1968).Google Scholar
  44. Gesler, R. M., and N. J. Kartinos: Contamination of blood stored in plastic packs. Lancet 1, 1227 (1970).PubMedGoogle Scholar
  45. Graham, P. R.: Phthalate ester plasticizers: Why and how they are used. Environ. Health Perspect. 3, 3 (1973).PubMedGoogle Scholar
  46. Guess, W. L., S. Haberman, D. Rowan, R. K. Bower, and J. Autian: Characterization of subtle toxicity of certain plastic components used in the manufacture of the polyvinyls. Amer. J. Hosp. Pharm. 24, 494 (1967).Google Scholar
  47. Gullbring, B.: The use of plastics in blood transfusion equipment with special regard to toxicity problems. Vox Sang. 9, 513 (1964).PubMedGoogle Scholar
  48. -, L. H. Eklund, and G. Svartz-Malmberg: Clinical and biological test methods applied to plastic products used in transfusion equipment. Vox Sang. 9, 530 (1964).PubMedGoogle Scholar
  49. Haagen-Smit, F. N. Hirosawa, and T. H. Wang: Volatile constituents of Zinfandel grapes, Vitis vinifera, Var. Zinfandel. Food Res. 14, 472 (1949).Google Scholar
  50. Haberman, S., W. L. Guess, D. F. Rowan, R. O. Bowman, and R. K. Bower: Effects of plastics and their additives on human serum proteins, antibodies, and developing chick embryos. Presented Reg. Tech. Conf., Soc. Plastics Eng., N.Y. Sect., pp. 28–43 (1967).Google Scholar
  51. - - - - - Effect of plastics and their additives on human serum proteins, antibodies, and developing chick embryos. Soc. Plastics Eng. J. 24, (3), 62 (1968).Google Scholar
  52. Hayashi, S., Y. Asakawa, T. Ishtoa, and T. Matsuura: Phthalate esters of Cryptotaenia canadensis D.C., var. japonica Makino (umbelliferae). Tetrahedron Letters 1967, 5061 (1967).Google Scholar
  53. Hayashi, T., and T. Nagai: Components of soil humic acids. VIII. Oxidative decomposition with alkaline potassium permanganate and nitric acid. Nippon Dojo-Hiryogaku Zasshi 31, 197 (1960).Google Scholar
  54. Hemy, G.: The Soviet chemical industry. New York: Barnes and Noble (1971).Google Scholar
  55. Hirose, T., R. Goldstein, and C. P. Bailey: Hemolysis of blood due to exposure to different types of plastic tubing and the influence of ethylene-oxide sterilization. J. Thoracic Cardiovascular Surg. 45, 245 (1963).Google Scholar
  56. Hites, R. A., and K. Biemann: Water pollution—Organic compounds in the Charles River, Boston. Science 178, 158 (1972).PubMedGoogle Scholar
  57. Hodge, H. C.: Acute toxicity for rats and mice of 2-ethyl hexanol and 2-ethyl hexyl phthalate. Proc. Soc. Exp. Biol. Med. 53, 20 (1943).Google Scholar
  58. -, M. R. Goldstein, and Wrightington: Acute toxicity for mice of phthalic acid and certain derivatives. Proc. Soc. Exp. Biol. Med. 99, 471 (1942).Google Scholar
  59. Homrowski, S. T., and M. Nikonorow: [Title unknown, cited in Piekacz (1971 a)]. Rocz Panstw Zakl Hig. 10, 321 (1959).Google Scholar
  60. Jaeger, R. J., and R. J. Rubin: Plasticizers from plastic devices extraction, metabolism, and accumulation by biological systems. Science 170, 460 (1970 a).PubMedGoogle Scholar
  61. - - Contamination of blood stored in plastic packs. Lancet 2, 151 (1970 b).PubMedGoogle Scholar
  62. - - Plasticizers from P.V.C. Lancet 2, 778 (1970 c).PubMedGoogle Scholar
  63. - - Migration of a phthalate ester plasticizer from polyvinyl chloride blood bags into stored human blood and its localization in human tissues. N. England J. Med. 287, 1114 (1972).Google Scholar
  64. - - Extraction, localization, and metabolism of di-2-ethylhexyl phthalate from PVC plastic medical devices. Environ. Health Perspect. 3, 95 (1973).PubMedGoogle Scholar
  65. Japan Plastics Industry Annual, Tokyo: Plastics Age Ltd. (1970).Google Scholar
  66. Jones, W. A., J. D. Warthen, and M. Jacobson: The occurrence of dibutyl phthalate in American cockroaches. Environ. Letters 4, 103 (1973).Google Scholar
  67. Karel, L., B. H. Landing, and T. S. Harvey: The intraperitoneal toxicity of some glycols, glycol esters, and phthalates in mice. J. Pharmacol. Exp. Therap. 90, 338 (1947).Google Scholar
  68. Keith, H. B., E. Ginn, G. R. Williams, and G. S. Campbell: Massive hemolysis in extracorporeal circulation. J. Thoracic Cardiovascular Surg. 41, 404 (1961).Google Scholar
  69. Kemp: Dissertation [Title unknown, cited in Spector (1956)]. Würzburg (1934).Google Scholar
  70. Kissmeyer-Nielden, F.: Platelets in blood stored in untreated and siliconed glass bottles and plastic bags. I. Studies in vitro. J. Clin. Pathol. 14, 626 (1961).Google Scholar
  71. -, and C. B. Madsen: Platelets in blood stored in untreated and siliconed glass bottles and plastic bags. II. Survival studies. J. Clin. Pathol. 14, 630 (1961).Google Scholar
  72. Klaus, A., and E. von Sydow: Aroma of cranberries. Acta Chem. Scand. 21, 2076 (1967).Google Scholar
  73. Klausmeier, R. E., and W. A. Jones: Microbial degradation of plasticizers. Develop. Ind. Microbiol. 2, 47 (1960).Google Scholar
  74. Knights, B. A.: Isolation of 4-hydroxyphthalide from oat grain. Nature 210, 1261 (1966).PubMedGoogle Scholar
  75. Kohler, F., W. Meise, and H. Ockenfels: Teratological determination of some thalidomide metabolites. Experientia 27, 1149 (1971).PubMedGoogle Scholar
  76. Kokurin, A. D., and K. A. Galutkina: Neutral oxygen compounds of heavy tar of bituminous shale. [Translated title] Zh. Prikl. Khim. 40, 887 (1967).Google Scholar
  77. Kowalski, Z., and E. Bassendowsa: Studies on the acute toxic action of phthalates used in the production of plastics. [Translated title] Med. Pracy. 16, 109 (1965).Google Scholar
  78. Krauskopf, L. G.: Studies on the toxicity of phthalates via ingestion. Environ. Health Perspect. 3, 61 (1973).PubMedGoogle Scholar
  79. Lawrence, W. H., J. L. Mitchell, W. L. Guess, and J. Autian: Toxicity of plastics used in medical practice. I. Investigation of tissue responses in animals by certain unit packaged polyvinyl chloride administration devices. J. Pharm. Sci. 52, 958 (1963).PubMedGoogle Scholar
  80. Lehman, A. J.: Insect repellants. Assoc. Food and Drug Officials U.S. Quart. Bull. 19, 87 (1955).Google Scholar
  81. Levinskas, G. J.: Inhalation toxicity tests. In: Flexible vinyls and human safety, Soc. of Plastic Eng., pp. 95–100 (1973).Google Scholar
  82. Livingston, J. R.: (1971). Unpublished work, cited in Krauskopf (1973).Google Scholar
  83. Loranskii, D. N., S. N. SMIRNITSKII, and E. N. Shakleina: Printsipy gigienicheskogo normirovaniia pri otsenke polimernykh stroietl’nykh materialov. Gig. Sanit. 35, 51 (1970).PubMedGoogle Scholar
  84. Mallette, F. S., and E. Von Haam: The toxicity and skin effects of compounds used in the rubber and plastics industries. II. Plasticizers. Arch. Ind. Hgy. Occup. Med. 6, 231 (1952).Google Scholar
  85. Marcel, Y. L., and S. P. Noel: Contamination of blood stored in plastic packs. Lancet 1, 35 (1970a).PubMedGoogle Scholar
  86. - - A plasticizer in lipid extracts of human blood. Chem. Phys. Lipids 4, 418 (1970b).Google Scholar
  87. Maslenko, A. A.: Normalization of the dibutyl phthalate level in reservoir waters. [Translated title] Gig. Naselennykh Mest., pp. 72–75 (1967).Google Scholar
  88. - Hygienic characteristics of dibutylphthalate and dioctylphthalate water pollutants. [Translated title] Gig. Sanit. 33, 102 (1968).PubMedGoogle Scholar
  89. - Effect of dioctyl phthalate on the organoleptic properties of water and the total sanitary system of reservoirs. [Translated title] Gig. Naselennykh Mest. 8, 80(1969).Google Scholar
  90. Matsuda, K., and M. Schnitzer: Reactions between fulvic acid, a soil humic material and dialkyl phthalates. Bull. Environ. Contain. Toxicol. 6, 200 (1971).Google Scholar
  91. Mayer, F. L., Jr., and H. O. Sander: Toxicology of phthalic esters on aquatic organisms. Environ. Health Perspect. 3, 153 (1973).PubMedGoogle Scholar
  92. -, D. L. Stalling, and J. L. Johnson: Phthalate esters as environmental contaminants. Nature 238, 411 (1972).PubMedGoogle Scholar
  93. McCandless, A. E.: Ileocolitis following exchange transfusion. Lancet 2, 762 (1971).PubMedGoogle Scholar
  94. McLaughlin, J., Jr., J. P. Marlaic, M. J. Verrett, M. K. Mutcher, and O. G. Fitzhugh: The injection of chemicals into the yolk sac of fertile eggs prior to incubation as a toxicity test. Toxicol. Applied Pharmacol. 5, 760 (1963).Google Scholar
  95. McOmie, W. A.: Certain aspects of the toxicity of diallyl phthalates. Fed. Proc. 5, 191 (1946).PubMedGoogle Scholar
  96. - (1949). Title unknown, cited in Spector (1956).Google Scholar
  97. -, and H. H. Anderson: Toxicity of diallyl phthalate. Univ. Calif. Publ. Pharmacol. 2, 205 (1947).Google Scholar
  98. Meijler, F. L., and D. Dürrer: The influence of poly-vinyl-chloride tubing on the isolated perfused rat’s heart. Vox Sang. 4, 239 (1959).Google Scholar
  99. Men’shikova, T. A.: Hygienic evaluation of dibutylphthalate in relation to the use of polymeric materials for finishing living quarters on ships. [Translated title] Gig. Sanit. 36, 23 (1971).PubMedGoogle Scholar
  100. Metcalf, R. L., G. M. Booth, C. K. Carter, D. J. Hansen, and P. Y. Lu: Uptake and fate of di-2-ethylhexyl phthalate in acquatic organisms and in a model ecosystem. Environ. Health Perspect. 4, 27 (1973).PubMedGoogle Scholar
  101. Meyler, F. L., A. F. Willebrand, and D. Dürrer: The influence of poly-vinylchloride (P.V.C.) tubing on the isolated perfused rat’s heart. Circ. Res. 8, 44 (1960).Google Scholar
  102. Milkov, L. E., M. V. Aldyreva, T. B. Popova, K. A. Lopukhova, I. U. L. Makakenko, L. M. Maliar, and T. K. Shakhova: The status of health of workers subjected to the effects of phthalate plasticizers in the production of artificial leather and film (with PVC base). [Translated title] Gig. Tr. Prof. Zabol. 13, 14 (1969).PubMedGoogle Scholar
  103. Mitsuhashi, H., T. Muramatsu, U. Nagai, T. Nakano, and K. Ueno: Studies on the constituents of Umbelliferae plants. VIII. Distribution of alkylphthalides in Umbelliferae plants. Chem. Pharm. Bull. 11, 1317 (1963).PubMedGoogle Scholar
  104. Miyoshi, T., and T. Harada: Formation of dibutylphthalate from 2-butyne-1, 4-diol by a soil bacterium. Biochim. Biophys. Acta 222, 684 (1970).PubMedGoogle Scholar
  105. Mokhanachev, I. G., and L. G. Aatakhova: Water soluble di- and tricarboxylic acids in tobacco smoke. Tabak (Moscow) 29(3), 31 (1968).Google Scholar
  106. Mori, S., K. Ota, M. Takada, and T. Ionu: Comparative studies of cyanoacrylate derivative in vivo. J. Biomed. Material Res. 1, 55 (1967).Google Scholar
  107. Morris, R. J.: Phthalic acid in the deep sea jellyfish Atolla. Nature 225, 1264 (1970).Google Scholar
  108. Nazir, D. J., M. Beroza, and P. P. Nair: Isolation and identification of di(2-ethylhexyl) phthalate—a component of heart muscle mitochondria. Fed. Proc. 26, 412 (1967).Google Scholar
  109. -, A. P. Alcaraz, B. A. Bierl, M. Beroza, and P. P. Nair: Isolation, identification, and specific localization of di-2-ethylhexyl phthalate in bovine heart muscle mitochondria. Biochem. 10, 4228 (1971).Google Scholar
  110. Neergaard, J., B. Nielsen, V. Faurby, D. H. Christensen, and O. F. Nielsen: Plasticizers in P.V.C. and the occurrence of hepatitis in a haemodialysis unit: A preliminary communication. Scand. J. Urol. Nephrol. 5, 141 (1971).PubMedGoogle Scholar
  111. Nematollahi, J., W. L. Guess, and J. Autian: Plasticizers in medical application. I. Analysis and toxicity evaluation of dialkyl benzenedicarboxylates. J. Pharm. Sci. 56, 1446 (1967).PubMedGoogle Scholar
  112. Nisbet, I. C. T., and A. F. Sarofilm: Rates and routes of transport of PCB’s in the environment. Environ. Health Perspect. 1, 21 (1972).PubMedGoogle Scholar
  113. Ogner, G., and M. Schnitzer: Humic substances—fulvic acid-dialkyl phthalate complexes and their role in pollution. Science 170, 317 (1970).PubMedGoogle Scholar
  114. Oppenheimer, B. S., E. T. Oppenheimer, A. P. Stout, and I. Danishefsky: Malignant tumors resulting from embedding plastic in rodents. Science 118, 305 (1953).PubMedGoogle Scholar
  115. - - , I. Danishefsky, A P. Scott, and F. R. Eirich: Further studies of polymers as carcinogenic agents in animals. Cancer Res. 15, 333 (1955).PubMedGoogle Scholar
  116. - - A. P. Stout, I. Danishefsky, and M. Willhite: The mechanism of carcinogenesis by plastic films. Acta Unio. Internat. Contra. Cancrum 15, 659 (1959).Google Scholar
  117. Ozge, A., M. Baldini, and R. Goldstein: Effect of plastic and glass surface on clot retraction and serotonin uptake of platelet-rich plasma stored at 4°C. J. Lab. Clin. Med. 63, 378 (1964).PubMedGoogle Scholar
  118. Parodi, P. W., and R. J. Dunstan: Unsaponifiable fraction of butterfat: Contamination with phthalic acid esters. Aust. J. Dairy Technol. 23(1), 20 (1968).Google Scholar
  119. Patty, F. A. (ed.): Industrial hygiene and toxicology, vol. 2. New York: Interscience (1967).Google Scholar
  120. Pazinski, H. J.: Phthalates in the environment. In: Flexible vinyls and human safety, Soc. of Plastic Eng. (1973).Google Scholar
  121. Perkins, E. G.: Formation of nonvolatile decomposition products in heated fats and oils. Food Technol. 21, 611 (1967 a).Google Scholar
  122. - Characterization of the nonvolatile compounds formed during the thermal oxidation of corn oil. II. Phthalate esters. J. Amer. Oil Chem. Soc. 44, 197 (1967 b).Google Scholar
  123. Perry, J. J., and H. W. Scheld: Oxidation of hydrocarbons by microorganisms isolated from soil. Can. J. Microbiol. 14, 403 (1968).PubMedGoogle Scholar
  124. Pfab, W.: Migration of phthalate plasticizers from lacquered aluminum foils on fatty foods. [Translated title] Deut. Lebensm.-Rundsch. 63(3), 72 (1967).Google Scholar
  125. Pfuderer, P., and A. A. Francis: The effect of phthalate esters on the heartrate of the goldfish. Fed. Proc. 32, 74 (1973).Google Scholar
  126. Phillips, H. F., and I. A. Breger: Isolation and identification of an ester from a crude oil. Geochim. Cosmochim. Acta 15, 51 (1958).Google Scholar
  127. Piekacz, H.: Effect of dibutyl phthalate and dioctyl phthalate on rat’s organism administered orally over a prolonged period. I. Use and toxic properties of dibutyl phthalate and dioctyl phthalate. [Translated title] Rocz Panstw Zakl Hig. 22, 55 (1971a).PubMedGoogle Scholar
  128. - Effect of dioctyl- and dibutylphthalates on rats during oral administration in prolonged experiments. II. Studies of subacute and chronic toxicity. [Translated title] Rocz Panstw Zakl Hig. 22, 295 (1971 b).PubMedGoogle Scholar
  129. - Influence on rat organism of dibutyl phthalate and dioctyl phthalate administered orally for a protracted time. III. Influence on fertility and fetus development. [Translated title] Rocz Panstw Zakl Hig. 22, 519 (1971c).PubMedGoogle Scholar
  130. Popov, L. A., and U. D. Yablochkin: Characteristics of gases released by polyvinyl chloride film. [Translated title] Gig. Sanit. 32, 114 (1967).Google Scholar
  131. Proenca da Cunha, A.: Analytical study of the essential oil of Eucalyptus punctata of Angola. [Translated title] Garcia Orta 14, 411 (1966).Google Scholar
  132. Protsenko, E. I.: Gonadotropic action of phthalic anhydride. [Translated title] Gig. Sanit. 35, 105 (1970).PubMedGoogle Scholar
  133. Radeva, M., and S. Dinoeva: Toxicity of dibutyl phthalate by oral application in albino rats. [Translated title] Khig. Zdraveopazvane 9, 510 (1966).Google Scholar
  134. Rall, D. P.: Risks, research, and reason. Fed. Proc. 32, 1766 (1973).PubMedGoogle Scholar
  135. Ranaudo, C., and O. Schettino: Colorimetric determination of phthalates in olive and olive husk oils. Rassegna Chimica 21, 171 (1969).Google Scholar
  136. Rolovic, Z., and M. Baldini: Comparative studies of the viability of human platelets stored at 4°C in plastic and glass containers. Transfusion 7, 204 (1967).PubMedGoogle Scholar
  137. Rubin, R. J.: Storage of aqueous solutions for parenteral infusion. Lancet 1, 965 (1972).PubMedGoogle Scholar
  138. -, and P. P. Nair: Plasticizers in human tissues. N. England J. Med. 288, 915 (1973).Google Scholar
  139. Schettino, O., and M. I. La Rotonda: Release of additives from surgical instruments and pharmaceutical containers made of poly (vinyl chloride) (PVC). I. Chromatographic detection of alkyl citrate and phthalate plasticizers. Boll. Soc. Ital. Biol. Sper. 45, 1337 (1969).PubMedGoogle Scholar
  140. Schinz, H., and C. F. Seidel: Untersuchungen über Aromastoffe. I. Über das Himbeeraroma. Helv. chim. Acta 40, 1839 (1957).Google Scholar
  141. Schmeltz, I., and W. S. Schlotzhauer: Nonvolatile acids of cigar smoke. Tobacco Sci. 6, 88 (1962); Tobacco 154(20), 32 (1962).Google Scholar
  142. Schmid, I. H., and P. Karrer: Über wasserlösliche Inhaltsstoffe von Papaver somniferum L. Helv. chim. Acta 28, 722 (1945).Google Scholar
  143. Schnitzer, M., and J. G. Desjardins: The alkaline permanganate oxidation of organic matter extracted from a podzol Bh horizon. Can. J. Soil Sci. 44, 272 (1964).Google Scholar
  144. Schulz, C. O., and R. J. Rubin: Distribution, metabolism, and excretion of di-2-ethylhexyl phthalate in the rat. Environ. Health Perspect. 3, 123 (1973).PubMedGoogle Scholar
  145. Scott, G.: Plastics packaging and coastal pollution. Internat. J. Environ. Studies 3, 35 (1972).Google Scholar
  146. Shaffer, C. B. M., C. P. Carpenter, and H. F. Smyth: Acute and subacute toxicity of di(2-ethylhexyl)phthalate with note upon its metabolism. J. Ind. Hyg. Toxicol. 27, 130 (1945).Google Scholar
  147. Sims, R.: Analysis of hepatocarcinogenic fish meal lipids. U.S. Fish and Wildlife Service, Res. Rept. No. 70, 178 (1967).Google Scholar
  148. Singh, A. R., W. H. Lawrence, and J. Autian: Teratogenicity of phthalate esters in rats. J. Pharm. Sci. 61, 51 (1972).PubMedGoogle Scholar
  149. Smith, C. C.: Toxicity of butyl stéarate, dibutyl sebacate, dibutyl phthalate and methoxyethyl oleate. Arch. Ind. Hyg. 7, 310 (1953).Google Scholar
  150. Smith, O. M.: Toxic properties of diethylphthalate. J. Amer. Pharm. Assoc. 13, 812 (1924).Google Scholar
  151. Smith, R. L., S. Fabro, H. Schumacher, and R. T. Williams: The relation between the chemical structure and embryotoxic activity of thalidomide and related compounds. Symp. Embryopathic Activ. Drugs. Univ. Col. London, pp. 194–209 (1965).Google Scholar
  152. Smyth, H. F., Jr., C. P. Carpenter, C. S. Weil, and U. C. Pozzani: Rangefinding toxicity data: List. Arch. Ind. Hyg. 10, 61 (1954).Google Scholar
  153. Spasovski, M.: The maximum allowable concentration of dibutyl phthalate. [Translated title] Khigiena 7, 38 (1964).Google Scholar
  154. Spector, W. S. (ed.): Handbook of toxicology. New York: Saunders (1956).Google Scholar
  155. Stalling, D. L., J. W. Hogan, and J. L. Johnson: Phthalate ester residues: Their metabolism and analysis in fish. Environ. Health Perspect. 3, 159 (1973).PubMedGoogle Scholar
  156. Stevens, K. L., J. Bomben, A. Lee, and W. H. McFadden: Volatiles from grapes. Muscat of Alexandria. J. Agr. Food Chem. 14, 249 (1966).Google Scholar
  157. Stewart, J. W., and M. F. Sturridge: Haemolysis caused by tubing in extracorporeal circulation. Lancet 1, 340 (1959).PubMedGoogle Scholar
  158. Sugiyama, N., C. Kashima, M. Yamamoto, T. Sugaya, and R. Mohri: Altenin. I. The isolation of Altenin from Alternaria kikuchiana. Bull. Chem. Soc. Japan 39, 1573 (1966).Google Scholar
  159. Swain, A. P., W. Rusaniwskj, and R. L. Stedman: Hexane-soluble substances of tobacco leaves. Chem. & Ind., pp. 435–436 (1961).Google Scholar
  160. Taborsky, R. G.: Isolation studies on a lipoidal portion of the bovine pineal gland. J. Agr. Food Chem. 15, 1073 (1967).Google Scholar
  161. Thiele, O. W., and H. G. Truper: Esters of phthalic acid as artifacts in bacterial lipids. Arch. Mikrobiol. 2, 91 (1972).Google Scholar
  162. Trimble, A. S., B. S. Goldman, J. K. Yao, L. K. Kovats, and W. G. Bigelow: Plastics—a source of chemical contamination in surgical research. Surgery 59, 857 (1966).PubMedGoogle Scholar
  163. Tyson, C. A.: (1972). Unpublished work, cited by Krauskopf (1973).Google Scholar
  164. Valeri, C. R., T. J. Contreras, H. Feingold, R. H. Shelbley, and R. J. Jaeger: Accumulation of di-2-ethylhexyl phthalate (DEHP) in whole blood, platelet concentrates and platelet-poor plasma. Environ. Health Perspect. 3, 103 (1973).PubMedGoogle Scholar
  165. Venrick, E. L., T. W. Backman, W. C. Bartram, C. L. Platt, M. S. Thornhill, and R. E. Yates: Man-made objects on the surface of the central North Pacific Ocean. Nature 241, 271 (1973).Google Scholar
  166. Verrett, M. J., M. K. Mutchler, W. F. Scott, E. F. Reynaldo, and J. McLaughlin: Teratogenic effects of captan and related compounds in the developing chicken embryo. Ann. N.Y. Acad. Sci. 160, 334 (1969).PubMedGoogle Scholar
  167. Wakayama, S., and S. Namba: The constituents of the flower oil of lily of the valley. Bull. Chem. Soc. Japan 38, 860 (1965).Google Scholar
  168. Walter, C. W.: A technique for collection, storage, and administration of unadulterated whole blood. In: Surgical forum 1950, Amer. Col. Surgeons. Philadelphia: Saunders (1951).Google Scholar
  169. Wildbrett, G.: Diffusion of phthalic acid esters from PVC milk tubing. Environ. Health Perspect. 3, 29 (1973).PubMedGoogle Scholar
  170. -, K. W. Evers, and F. Kiermeier: Application of plastics in the food industry. XI. Detection of monomeric plasticizers contained in plastics in milk. Z. Lebensm.-Unters. Forsh. 137, 356 (1968).Google Scholar
  171. - - - Application of plastics in foods. VII. Migration of monomeric plasticizers from PVC milk tubing into cleansing solutions. Fette, Seifen, Anstrichm. 71, 330 (1969).Google Scholar
  172. - - - Untersuchungen und Betrachtungen zur Anwendung von Kunststoffen für Lebensmittel. XIII. Zum Verhalten von Kunststoffen gegenüber Milch. Z. Lebensm.-Unters. Forsch. 12, 205 (1970).Google Scholar
  173. Williams, R. T.: Thalidomide: A study of biochemical teratology. Arch. Environ. Health 16, 493 (1968).PubMedGoogle Scholar
  174. Woggon, H., and U. Koehler: The testing of plastics consumer goods. Polarographic determination of bis(2-ethylhexyl) phthalate and study of its migration tendency. Kunststoffe 57, 583 (1967).Google Scholar
  175. Woodwell, G. M., P. P. Craig, and H. A. Johnson: DDT in the biosphere: Where does it go? Science 174, 1101 (1971).PubMedGoogle Scholar
  176. Yamamoto, A., and T. Omori: The flavors in sake. VIII. Separation and identification of phthalic acid ester, p-hydroxybenzoic acid, and its ester. Nippon Nogei Kagaku Kaishi 38, 231 (1964).Google Scholar
  177. Zitko, V.: Determination of phthalates in biological samples. Internat. J. Environ. Anal. Chem. 2, 241 (1973).Google Scholar

Copyright information

© Springer-Verlag New York Inc 1975

Authors and Affiliations

  • David B. Peakall
    • 1
  1. 1.Section of Ecology and Systematics, Langmuir LaboratoryCornell UniversityIthacaUSA

Personalised recommendations