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Chemical Compound Review

AC1NX425     3,4-dioctylphthalate

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Disease relevance of 3,4-dioctylbenzene-1,2-dicarboxylic acid

  • Cessation of exposure to DEHP initiated partial to complete recovery from toxicity in most cases [1].
  • Studies in the rat indicated that exposure to doses of 1/6 and 1/12 of the LD50 per day of DEHP resulted in a reduced gain in body weight compared to controls [2].
  • Both DEHP and MEHP induced 8AG/6TG-resistant mutation, chromosomal aberrations and morphological transformation in the embryonic cells of the Syrian golden hamster [3].
  • Prolonged exposure to the peroxisome proliferator, DEHP, causes hepatic hyperplasia and liver tumors in rats and mice [4].
  • The data indicate that high levels of peroxisome proliferation and hepatomegaly are associated with DEHP hepatocarcinogenesis in rodent liver, and that the tumorigenic process may be arrested by cessation of DEHP treatment, suggesting that extended treatment with DEHP acts to promote tumor growth [5].

High impact information on 3,4-dioctylbenzene-1,2-dicarboxylic acid

  • The nongenotoxic carcinogens methylclofenapate and DEHP cause an initial hyperplastic response due to the rapid conversion of binucleated cells to mononucleated tetraploids by amitotic cytokinesis following S phase [6].
  • The mRNA levels of HMG-CoA reductase were not changed by either DEHP or fat diet, while DEHP increased cytosolic HMG-CoA synthase 2.5-fold [7].
  • DEHP did not change the mRNA levels for fatty acid synthase [7].
  • Rats fed with a fat diet significantly increased the expression of mitochondrial HMG-CoA synthase, CPT I and CPT II 3-fold in all cases, while 2-(diethylhexyl)phthalate (DEHP) produced increases in the expression of these genes (5-, 4- and 12-fold, respectively) [7].
  • Wy-14643 was also stronger than DEHP in stimulating c-jun expression, whereas both PPs were fairly strong inducers of jun-B and jun-D [8].

Chemical compound and disease context of 3,4-dioctylbenzene-1,2-dicarboxylic acid

  • The metabolism and toxicity of the ubiquitous plasticizer, bis-(2-ethylhexyl) phthalate (DEHP), and its principal metabolite, mono-(2-ethylhexyl) phthalate (MEHP), have been extensively investigated [9].
  • From the culture broth of a fungus, two metabolites have been isolated: bis(2-ethylhexyl)phthalate (DEHP) precedently isolated from Streptomyces sp. and 2-(4-hydroxyphenyl)-2-oxoacetaldehyde oxime (PHBA) here reported as a natural compound in the (E)-s-cis configuration [10].
  • Between 1998 and 2000 an Expert Panel convened by the National Toxicology Program's Center for the Evaluation of Risks to Human Reproduction (NTP-CERHR) reviewed information related to the developmental and reproductive toxicity of seven phthalate esters; DBP, BBP, DnHP, DEHP, DnOP, DINP, and DIDP [11].
  • The results suggest use of vitamin E to prevent harmful effects of repeated transfusion of DEHP containing blood as in thalassemia patient [12].

Biological context of 3,4-dioctylbenzene-1,2-dicarboxylic acid


Anatomical context of 3,4-dioctylbenzene-1,2-dicarboxylic acid

  • Dietary exposure of adult male F344 rats to 0, 320, 1250, 5000, or 20,000 ppm DEHP for 60 consecutive days resulted in a dose-dependent reduction in total body, testis, epididymis, and prostate weights at 5000 and 20,000 ppm [1].
  • Together with the CHO and micronucleus data, these findings suggest that DEHP has a low probability of causing genetic damage capable of being transmitted through the male germ line [2].
  • Transfusion of these platelets into six adult patients with leukemia resulted in peak blood plasma levels of DEHP ranging from 0.34 to 0.83 mg/dl (approximately 0.02 mg/dl plasma per mg DEHP administered per square meter of surface area) [13].
  • Labeling of liver tissue from DEHP-treated rats with rabbit immune IgG made to the purified microsomal hydratase followed by gold conjugated goat anti-rabbit IgG suggested a single subcellular site for the bifunctional hydratase--the peroxisomal organelle [17].
  • The alpha-, beta- and p120-catenins were detected in the basal compartment of seminiferous tubules in similar localization and IF pattern for DEHP and control groups [18].

Associations of 3,4-dioctylbenzene-1,2-dicarboxylic acid with other chemical compounds

  • After 4 hr incubation in vitro, dioctylphthalate and benzylbutylphthalate significantly inhibited vasopressin-stimulated water flow in toad bladder [19].
  • Rat liver peroxisomes were markedly proliferated by administration of dioctyl phthalate (DEHP) for 2 weeks [20].
  • The present study explored whether the antiandrogenic action of DEHP occurs by (1) inhibiting testosterone (T) production, or by (2) inhibiting androgen action by binding to the androgen receptor (AR) [21].
  • Mono(2-ethylhexyl)phthalate (MEHP), the primary metabolite of the plasticizer bis(2-ethylhexyl)phthalate (DEHP), was given to guinea pigs and mice and the methods for the isolation, separation and analysis of its metabolites in urine were developed [22].
  • Maximum and minimum mean concentrations in the total diet samples were: 0.09-0.19 mg DBP/kg, 0.017-0.019 mg BBP/kg, 0.11-0.18 mg DEHP/kg and 0.13-0.14 mg DEHA/kg [23].

Gene context of 3,4-dioctylbenzene-1,2-dicarboxylic acid


Analytical, diagnostic and therapeutic context of 3,4-dioctylbenzene-1,2-dicarboxylic acid


  1. Effects of di(2-ethylhexyl) phthalate on the gonadal pathophysiology, sperm morphology, and reproductive performance of male rats. Agarwal, D.K., Eustis, S., Lamb, J.C., Reel, J.R., Kluwe, W.M. Environ. Health Perspect. (1986) [Pubmed]
  2. Genetic toxicology of phthalate esters: mutagenic and other genotoxic effects. Douglas, G.R., Hugenholtz, A.P., Blakey, D.H. Environ. Health Perspect. (1986) [Pubmed]
  3. Mutagenic/carcinogenic potential of DEHP and MEHP. Tomita, I., Nakamura, Y., Aoki, N., Inui, N. Environ. Health Perspect. (1982) [Pubmed]
  4. Suppression of cytochrome P450 Cyp2f2 mRNA levels in mice by the peroxisome proliferator diethylhexylphthalate. Ye, X., Lu, L., Gill, S.S. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  5. Chronic peroxisome proliferation and hepatomegaly associated with the hepatocellular tumorigenesis of di(2-ethylhexyl)phthalate and the effects of recovery. David, R.M., Moore, M.R., Cifone, M.A., Finney, D.C., Guest, D. Toxicol. Sci. (1999) [Pubmed]
  6. A cytological comparison between regeneration, hyperplasia and early neoplasia in the rat liver. Styles, J.A., Kelly, M., Elcombe, C.R. Carcinogenesis (1987) [Pubmed]
  7. The effect of etomoxir on the mRNA levels of enzymes involved in ketogenesis and cholesterogenesis in rat liver. Asins, G., Serra, D., Hegardt, F.G. Biochem. Pharmacol. (1994) [Pubmed]
  8. Activation of immediate-early gene expression by peroxisome proliferators in vitro. Ledwith, B.J., Manam, S., Troilo, P., Joslyn, D.J., Galloway, S.M., Nichols, W.W. Mol. Carcinog. (1993) [Pubmed]
  9. The in vitro serum protein-binding characteristics of bis-(2-ethylhexyl) phthalate and its principal metabolite, mono-(2-ethylhexyl) phthalate. Griffiths, W.C., Camara, P.D., Saritelli, A., Gentile, J. Environ. Health Perspect. (1988) [Pubmed]
  10. Isolation, structural identification and biological activity of two metabolites produced by Penicillium olsonii Bainier and Sartory. Amade, P., Mallea, M., Bouaïcha, N. J. Antibiot. (1994) [Pubmed]
  11. NTP center for the evaluation of risks to human reproduction reports on phthalates: addressing the data gaps. McKee, R.H., Butala, J.H., David, R.M., Gans, G. Reprod. Toxicol. (2004) [Pubmed]
  12. Vitamin E prevents deleterious effects of di (2-ethyl hexyl) phthalate, a plasticizer used in PVC blood storage bags. Dhanya, C.R., Gayathri, N.S., Mithra, K., Nair, K.V., Kurup, P.A. Indian J. Exp. Biol. (2004) [Pubmed]
  13. Fate in humans of the plasticizer, di-2-ethylhexyl phthalate, arising from transfusion of platelets stored in vinyl plastic bags. Rubin, R.J., Schiffer, C.A. Transfusion (1976) [Pubmed]
  14. Teratogenicity/fetotoxicity of DEHP in mice. Tomita, I., Nakamura, Y., Yagi, Y., Tutikawa, K. Environ. Health Perspect. (1982) [Pubmed]
  15. Effects of bis(2-ethylhexyl) phthalate (DEHP) on secondary sex ratio of mice in a cross-mating study. Tanaka, T. Food Chem. Toxicol. (2003) [Pubmed]
  16. Bis-(2-ethylhexyl) phthalate, an ubiquitous environmental contaminant. Griffiths, W.C., Camara, P., Lerner, K.S. Ann. Clin. Lab. Sci. (1985) [Pubmed]
  17. Source of the hepatic microsomal trans-2-enoyl CoA hydratase bifunctional protein: endoplasmic reticulum or peroxisomes. Ghesquier, D., Cook, L., Nagi, M.N., MacAlister, T.J., Cinti, D.L. Arch. Biochem. Biophys. (1987) [Pubmed]
  18. Effect of di-(2-ethylhexyl) phthalate on N-cadherin and catenin protein expression in rat testis. Sobarzo, C.M., Lustig, L., Ponzio, R., Denduchis, B. Reprod. Toxicol. (2006) [Pubmed]
  19. Effect of phthalate acid esters on transport in toad bladder membrane. Sabatini, S., Fracasso, A., Bazzato, G., Kurtzman, N.A. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  20. Formation of autophagosomes during degradation of excess peroxisomes induced by administration of dioctyl phthalate. Yokota, S. Eur. J. Cell Biol. (1993) [Pubmed]
  21. The plasticizer diethylhexyl phthalate induces malformations by decreasing fetal testosterone synthesis during sexual differentiation in the male rat. Parks, L.G., Ostby, J.S., Lambright, C.R., Abbott, B.D., Klinefelter, G.R., Barlow, N.J., Gray, L.E. Toxicol. Sci. (2000) [Pubmed]
  22. Chromatographic fractionation and analysis by mass spectrometry of conjugated metabolites of bis(2-ethylhexyl)phthalate in urine. Egestad, B., Green, G., Sjöberg, P., Klasson-Wehler, E., Gustafsson, J. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  23. Plasticizers in total diet samples, baby food and infant formulae. Petersen, J.H., Breindahl, T. Food additives and contaminants. (2000) [Pubmed]
  24. Regulation of phase I and phase II steroid metabolism enzymes by PPAR alpha activators. Fan, L.Q., You, L., Brown-Borg, H., Brown, S., Edwards, R.J., Corton, J.C. Toxicology (2004) [Pubmed]
  25. Effects of peroxisome proliferators and/or hypothyroidism on xenobiotic-metabolizing enzymes in rat testis. Mehrotra, K., Morgenstern, R., Lundqvist, G., Becedas, L., Bengtsson Ahlberg, M., Georgellis, A. Chem. Biol. Interact. (1997) [Pubmed]
  26. Plasticizers as contaminants in commercial ethanol. Goldstein, D.B., Feistner, G.J., Faull, K.F., Tomer, K.B. Alcohol. Clin. Exp. Res. (1987) [Pubmed]
  27. Promoting activity of di(2-ethylhexyl)phthalate in rat liver foci bioassay. Oesterle, D., Deml, E. J. Cancer Res. Clin. Oncol. (1988) [Pubmed]
  28. Assessment of parameters associated to the risk of PVC catheter reuse. Granados, D.L., Jiménez, A., Cuadrado, T.R. J. Biomed. Mater. Res. (2001) [Pubmed]
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