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Chemical Compound Review

benzoate     benzoate

Synonyms: Tennplas, Phenylformate, Benzeneformate, Retarded BA, Oracyclic acid, ...
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Disease relevance of benzoic acid


Psychiatry related information on benzoic acid


High impact information on benzoic acid

  • The bactericidal activity of the MPO-supplemented system is inhibited by catalase, benzoate, azide, DABCO, and histidine but not by SOD or mannitol [11].
  • Quenching OH. and 1O2, presumed products of O2--H2O2 interaction, by mannitol, benzoate, diazabicyclooctane, and histidine, also inhibited toxoplasma killing by xanthine-xanthine oxidase [12].
  • Using a novel in vivo microscopic method, we have measured bicarbonate secretion and epithelial cell intracellular pH (pH(i)), and we have followed cell injury in the presence of the anion transport inhibitor DIDS and the Cl(-) channel inhibitor, 5-nitro-2-(3-phenylpropylamino) benzoic acid (NPPB) [13].
  • Because Fas-induced apoptosis of hepatocytes involves mitochondrial damages and potential reactive oxygen species (ROS) overproduction, we investigated whether manganese III tetrakis (5,10,15,20 benzoic acid) (MnTBAP), a nonpeptidyl mimic of superoxide dismutase (SOD), can inhibit Fas-induced ALF [14].
  • Neither superoxide dismutase, catalase, nor sodium benzoate offered any protection against ethanol-induced injury, indicating that neither superoxide anion, hydrogen peroxide, nor the hydroxyl radical is involved [15].

Chemical compound and disease context of benzoic acid


Biological context of benzoic acid

  • The meta-cleavage operon of the TOL plasmid pWW0 of Pseudomonas putida contains 13 genes responsible for the oxidation of benzoate and toluates to Krebs cycle intermediates via estradiol (meta) cleavage of (methyl)catechol [21].
  • During the life span of the flower, the levels of methyl benzoate emission, BAMT activity, BAMT gene expression, and the amounts of BAMT protein and benzoic acid are developmentally and differentially regulated [22].
  • Methyl benzoate is produced in upper and lower snapdragon petal lobes by enzymatic methylation of benzoic acid in the reaction catalyzed by S-adenosyl-L-methionine:benzoic acid carboxyl methyltransferase (BAMT) [23].
  • The xylABC operon on the TOL plasmid directs the synthesis of enzymes for conversion of toluene to benzoate and is positively controlled by the regulatory gene xylR [24].
  • Physiological data and DNA sequence analyses indicate that the benzoate pathway consists of unusual enzymes for ring reduction and cleavage interposed among enzymes homologous to those catalyzing fatty acid degradation [18].

Anatomical context of benzoic acid

  • This analogue was used to identify NPA-binding proteins in fractions highly enriched for plasma membrane vesicles isolated from maize coleoptiles (Zea mays L.). Competition studies showed that binding of [3H2]N3NPA to maize plasma membrane vesicles was blocked by nonradioactive NPA but not by benzoic acid [25].
  • After injections of estradiol benzoate or oil vehicle to the hosts for 20 successive days, the grafts were processed for semiquantitative electron microscopic study to examine synaptic density in the neuropil [26].
  • The HL-60 nuclear receptor exhibited high-affinity binding of RA and its benzoic acid analogs Ch55, Ch30, Ro 13-7410, and SRI 6409-40 and low-affinity binding of retinol, Ro 8-8717, and SRI 5442-60, correlating well with the biological activity of these compounds in HL-60 cells [27].
  • Thus, the studies show that benzoate metabolism reflects mitochondrial function in BDL rats both in vivo and in vitro, and that mitochondrial proliferation compensates for the observed decrease in benzoic acid metabolism in isolated mitochondria in vitro [28].
  • METHODS: A newborn with NKH diagnosed prenatally following the neonatal death of a previous affected sibling was treated from birth with oral sodium benzoate (250 mg/kg/day) and the NMDA receptor antagonist ketamine (15 mg/kg/day) immediately after sampling cord blood and cerebrospinal fluid (CSF) for glycine determination [29].

Associations of benzoic acid with other chemical compounds

  • This study shows that they are also activated by low external pH, sorbate, benzoate or ethanol stress [30].
  • We constructed pWW0 mutants defective in the xylT gene, and found that these mutants were not able to grow on p-toluate while they were still capable of growing on benzoate and m-toluate [21].
  • Our results also suggest that similar molecular mechanisms are involved in the regulation of methyl benzoate production in diurnally (snapdragon) and nocturnally (tobacco and petunia) emitting plants [23].
  • INTERVENTIONS: Maximal exercise treadmill testing and exercise echocardiography were done at baseline, after acute ingestion of a placebo beverage (97% caffeine-free coffee), or after drinking an identical beverage containing 250 mg of caffeine sodium benzoate [31].
  • Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic Acid and enhancement in auxin transport [32].

Gene context of benzoic acid

  • The Saccharomyces cerevisiae ATP-binding cassette (ABC) transporter Pdr12p effluxes weak acids such as sorbate and benzoate, thus mediating stress adaptation [33].
  • The ZbYME2 gene from the food spoilage yeast Zygosaccharomyces bailii confers not only YME2 functions in Saccharomyces cerevisiae, but also the capacity for catabolism of sorbate and benzoate, two major weak organic acid preservatives [34].
  • Four novel receptors were isolated from fish, dog, pig, and monkey for this study and combined with a previously reported set of related receptors including human PXR, rabbit PXR, mouse PXR, chicken CXR, frog benzoate X receptors (BXRalpha, BXRbeta), and human and mouse CAR [35].
  • Benzoate utilization by S. cerevisiae expressing ZbYME2 requires a functional mitochondrial respiratory chain, but not the native Yme1p and Yme2p of the mitochondrion [34].
  • The possible role of benzoate in the antioxidant activity of PRDX5 is discussed [36].

Analytical, diagnostic and therapeutic context of benzoic acid

  • The number of sodium channels was assessed with a radioligand assay using the sodium channel-specific toxin [3H]batrachotoxinin benzoate ([3H]BTXB) [37].
  • On day 2, similar behavioral patterns with still more pronounced differences were observed between estradiol benzoate and ovariectomized control groups in struggling, immobility, and swimming [38].
  • To confirm that these increases were steroid hormone dependent, we compared vehicle-treated ovariectomized females with ovariectomized females treated with estradiol benzoate and P. Northern analysis and in situ hybridizations showed that the Hsc73 gene is enhanced by E and P in the pituitary and subregions of the VMH [39].
  • The cellular lipids were extracted, the individual phospholipid classes were isolated, lipid phosphorus content was determined, and the lipids were converted to diglyceride benzoate derivatives for separation and quantitation of the subclasses by high performance liquid chromatography [40].
  • Therapy with a low-protein diet, lactulose, and sodium benzoate has prevented recurrence of hyperammonemia and symptoms [41].


  1. Treatment of episodic hyperammonemia in children with inborn errors of urea synthesis. Brusilow, S.W., Danney, M., Waber, L.J., Batshaw, M., Burton, B., Levitsky, L., Roth, K., McKeethren, C., Ward, J. N. Engl. J. Med. (1984) [Pubmed]
  2. Attraction by repellents: an error in sensory information processing by bacterial mutants. Muskavitch, M.A., Kort, E.N., Springer, M.S., Goy, M.F., Adler, J. Science (1978) [Pubmed]
  3. Amino acid acylation: a mechanism of nitrogen excretion in inborn errors of urea synthesis. Brusilow, S., Tinker, J., Batshaw, M.L. Science (1980) [Pubmed]
  4. Is benzoic acid really harmful in cases of atopy and urticaria? Lahti, A., Hannuksela, M. Lancet (1981) [Pubmed]
  5. Anaphylaxis with sodium benzoate. Michils, A., Vandermoten, G., Duchateau, J., Yernault, J.C. Lancet (1991) [Pubmed]
  6. Hormonal priming and triggering of maternal behavior in the rat with special reference to the relations between estrogen receptor binding and ER mRNA in specific brain regions. Rosenblatt, J.S., Wagner, C.K., Morrell, J.I. Psychoneuroendocrinology (1994) [Pubmed]
  7. Effects of neonatal estrogen on hypothalamic deoxyribonucleases and DNA in the female rat. Litteria, M. Exp. Neurol. (1987) [Pubmed]
  8. Structure of macrophomate synthase. Ose, T., Watanabe, K., Yao, M., Honma, M., Oikawa, H., Tanaka, I. Acta Crystallogr. D Biol. Crystallogr. (2004) [Pubmed]
  9. Estradiol benzoate potentiates neuroactive steroids' effects on pain sensitivity. Frye, C.A., Duncan, J.E. Pharmacol. Biochem. Behav. (1996) [Pubmed]
  10. Benzoate treatment and the glycine index in nonketotic hyperglycinaemia. Van Hove, J.L., Vande Kerckhove, K., Hennermann, J.B., Mahieu, V., Declercq, P., Mertens, S., De Becker, M., Kishnani, P.S., Jaeken, J. J. Inherit. Metab. Dis. (2005) [Pubmed]
  11. Bactericidal activity of a superoxide anion-generating system. A model for the polymorphonuclear leukocyte. Rosen, H., Klebanoff, S.J. J. Exp. Med. (1979) [Pubmed]
  12. Macrophage oxygen-dependent antimicrobial activity. I. Susceptibility of Toxoplasma gondii to oxygen intermediates. Murray, H.W., Cohn, Z.A. J. Exp. Med. (1979) [Pubmed]
  13. Cellular bicarbonate protects rat duodenal mucosa from acid-induced injury. Akiba, Y., Furukawa, O., Guth, P.H., Engel, E., Nastaskin, I., Sassani, P., Dukkipatis, R., Pushkin, A., Kurtz, I., Kaunitz, J.D. J. Clin. Invest. (2001) [Pubmed]
  14. The superoxide dismutase mimetic MnTBAP prevents Fas-induced acute liver failure in the mouse. Malassagne, B., Ferret, P.J., Hammoud, R., Tulliez, M., Bedda, S., Trébéden, H., Jaffray, P., Calmus, Y., Weill, B., Batteux, F. Gastroenterology (2001) [Pubmed]
  15. Ethanol-induced injury to the rat gastric mucosa. Role of neutrophils and xanthine oxidase-derived radicals. Kvietys, P.R., Twohig, B., Danzell, J., Specian, R.D. Gastroenterology (1990) [Pubmed]
  16. Heterogeneity of prolactin responses to oestradiol benzoate in women with prolactinomas. White, M.C., Anapliotou, M., Rosenstock, J., Mashiter, K., Joplin, G.F. Lancet (1981) [Pubmed]
  17. Interaction of two LysR-type regulatory proteins CatR and ClcR with heterologous promoters: functional and evolutionary implications. Parsek, M.R., McFall, S.M., Shinabarger, D.L., Chakrabarty, A.M. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  18. A cluster of bacterial genes for anaerobic benzene ring biodegradation. Egland, P.G., Pelletier, D.A., Dispensa, M., Gibson, J., Harwood, C.S. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  19. Gentamicin effects on renal ischemia/reperfusion injury. Zager, R.A. Circ. Res. (1992) [Pubmed]
  20. Detection of Epstein-Barr virus messenger RNA in Reed-Sternberg cells of Hodgkin's disease by in situ hybridization with biotinylated probes on specially processed modified acetone methyl benzoate xylene (ModAMeX) sections. Brousset, P., Chittal, S., Schlaifer, D., Icart, J., Payen, C., Rigal-Huguet, F., Voigt, J.J., Delsol, G. Blood (1991) [Pubmed]
  21. In vivo reactivation of catechol 2,3-dioxygenase mediated by a chloroplast-type ferredoxin: a bacterial strategy to expand the substrate specificity of aromatic degradative pathways. Polissi, A., Harayama, S. EMBO J. (1993) [Pubmed]
  22. Developmental regulation of methyl benzoate biosynthesis and emission in snapdragon flowers. Dudareva, N., Murfitt, L.M., Mann, C.J., Gorenstein, N., Kolosova, N., Kish, C.M., Bonham, C., Wood, K. Plant Cell (2000) [Pubmed]
  23. Regulation of circadian methyl benzoate emission in diurnally and nocturnally emitting plants. Kolosova, N., Gorenstein, N., Kish, C.M., Dudareva, N. Plant Cell (2001) [Pubmed]
  24. Nucleotide sequence surrounding transcription initiation site of xylABC operon on TOL plasmid of Pseudomonas putida. Inouye, S., Ebina, Y., Nakazawa, A., Nakazawa, T. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  25. 5'-Azido-[3,6-3H2]-1-napthylphthalamic acid, a photoactivatable probe for naphthylphthalamic acid receptor proteins from higher plants: identification of a 23-kDa protein from maize coleoptile plasma membranes. Zettl, R., Feldwisch, J., Boland, W., Schell, J., Palme, K. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  26. Synapse formation in response to estrogen in the medial amygdala developing in the eye. Nishizuka, M., Arai, Y. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  27. Identification and characterization of nuclear retinoic acid-binding activity in human myeloblastic leukemia HL-60 cells. Nervi, C., Grippo, J.F., Sherman, M.I., George, M.D., Jetten, A.M. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  28. Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis. Krähenbühl, L., Reichen, J., Talos, C., Krähenbühl, S. Hepatology (1997) [Pubmed]
  29. Treatment from birth of nonketotic hyperglycinemia due to a novel GLDC mutation. Korman, S.H., Wexler, I.D., Gutman, A., Rolland, M.O., Kanno, J., Kure, S. Ann. Neurol. (2006) [Pubmed]
  30. The HOG pathway controls osmotic regulation of transcription via the stress response element (STRE) of the Saccharomyces cerevisiae CTT1 gene. Schüller, C., Brewster, J.L., Alexander, M.R., Gustin, M.C., Ruis, H. EMBO J. (1994) [Pubmed]
  31. The effect of caffeine on exercise tolerance and left ventricular function in patients with coronary artery disease. Hirsch, A.T., Gervino, E.V., Nakao, S., Come, P.C., Silverman, K.J., Grossman, W. Ann. Intern. Med. (1989) [Pubmed]
  32. Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic Acid and enhancement in auxin transport. Orlova, I., Marshall-Colón, A., Schnepp, J., Wood, B., Varbanova, M., Fridman, E., Blakeslee, J.J., Peer, W.A., Murphy, A.S., Rhodes, D., Pichersky, E., Dudareva, N. Plant Cell (2006) [Pubmed]
  33. War1p, a novel transcription factor controlling weak acid stress response in yeast. Kren, A., Mamnun, Y.M., Bauer, B.E., Schüller, C., Wolfger, H., Hatzixanthis, K., Mollapour, M., Gregori, C., Piper, P., Kuchler, K. Mol. Cell. Biol. (2003) [Pubmed]
  34. The ZbYME2 gene from the food spoilage yeast Zygosaccharomyces bailii confers not only YME2 functions in Saccharomyces cerevisiae, but also the capacity for catabolism of sorbate and benzoate, two major weak organic acid preservatives. Mollapour, M., Piper, P.W. Mol. Microbiol. (2001) [Pubmed]
  35. Pregnane X receptor (PXR), constitutive androstane receptor (CAR), and benzoate X receptor (BXR) define three pharmacologically distinct classes of nuclear receptors. Moore, L.B., Maglich, J.M., McKee, D.D., Wisely, B., Willson, T.M., Kliewer, S.A., Lambert, M.H., Moore, J.T. Mol. Endocrinol. (2002) [Pubmed]
  36. Crystal structure of human peroxiredoxin 5, a novel type of mammalian peroxiredoxin at 1.5 A resolution. Declercq, J.P., Evrard, C., Clippe, A., Stricht, D.V., Bernard, A., Knoops, B. J. Mol. Biol. (2001) [Pubmed]
  37. Upregulation of the rat cardiac sodium channel by in vivo treatment with a class I antiarrhythmic drug. Taouis, M., Sheldon, R.S., Duff, H.J. J. Clin. Invest. (1991) [Pubmed]
  38. Estrogen alters behavior and forebrain c-fos expression in ovariectomized rats subjected to the forced swim test. Rachman, I.M., Unnerstall, J.R., Pfaff, D.W., Cohen, R.S. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  39. The 70-kDa heat shock cognate protein (Hsc73) gene is enhanced by ovarian hormones in the ventromedial hypothalamus. Krebs, C.J., Jarvis, E.D., Pfaff, D.W. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  40. Ether-linked phosphoglyceride content of human leukemia cells. Chabot, M.C., Greene, D.G., Brockschmidt, J.K., Capizzi, R.L., Wykle, R.L. Cancer Res. (1990) [Pubmed]
  41. Clinical features of carbamyl phosphate synthetase-I deficiency in an adult. Call, G., Seay, A.R., Sherry, R., Qureshi, I.A. Ann. Neurol. (1984) [Pubmed]
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