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Chemical Compound Review

sorbic acid     (2E,4E)-hexa-2,4-dienoic acid

Synonyms: Panosorb, Sorbistat, Preservastat, Sorbinsaeure, trans,trans-SA, ...
 
 
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Disease relevance of POTASSIUM SORBATE

 

Psychiatry related information on POTASSIUM SORBATE

  • The results showed that treatment with potassium sorbate did not affect the organoleptic properties of the cheeses, except that a slight objectionable bitter flavour was observed in fresh cheeses treated with sorbate using the techniques of dipping or in brine salting then it was disappeared during storage [6].
 

High impact information on POTASSIUM SORBATE

 

Chemical compound and disease context of POTASSIUM SORBATE

  • Effect of processing variables on the outgrowth of Clostridium sporogenes PA 3679 spores in comminuted meat cured with sorbic acid and sodium nitrite [12].
  • On the basis of the finding that sorbic acid (SA)-induced hepatoma was correlated with the depletion of reduced glutathione (GSH) in mouse liver (Tsuchiya et al., Mutation Res 130: 267-262, 1984), the possible conversion of SA to a metabolite which is reactive with SH-compounds was studied [13].
  • All four possible stereoisomers of lactone II isolated from Streptomyces sp. Go 40/10, an autoregulator, have been efficiently synthesized in a stereoselective manner starting from (S)-malic acid and sorbic acid, and the absolute configuration was determined to be 2S, 3S, 9R, 10S [14].
  • The effects of potassium sorbate, sodium hypophosphite, sodium tripolyphosphate, sodium nitrite, and linoleic acid on the germination and outgrowth of Clostridium botulinum type E spores were studied in microcultures [15].
  • CAL, MN, and DMSO, applied to different parts of the guinea pig body, produced only erythema most frequently on the upper back, but BA, SA, and CA did not cause any reactions [16].
 

Biological context of POTASSIUM SORBATE

 

Anatomical context of POTASSIUM SORBATE

 

Associations of POTASSIUM SORBATE with other chemical compounds

 

Gene context of POTASSIUM SORBATE

  • Deletion of BTN1, BTN2, or HSP30 does not alter cytosolic pH but diminishes pH buffering capacity and causes poor growth at low pH in a medium containing sorbic acid, a condition known to result in disturbed intracellular pH homeostasis [30].
  • Sorbic acid appeared to stimulate plasma membrane H+-ATPase activity in both PMA1 and pma1-205 [31].
  • Subsequently, we demonstrated that a deletion mutant of Hsp26 was sensitive to sorbic acid [32].
  • Similarly, of 6144 ORFs, 72 (1.17%) showed greater than a 1.4-fold decrease in transcript level and only one of these, PCK1, was decreased greater than two-fold Functional categories of genes that were induced by sorbic acid stress included cell stress (particularly oxidative stress), transposon function, mating response and energy generation [32].
  • However, a glycolytic mutant, with about one-third the normal pyruvate kinase and phosphofructokinase activity and hence a reduced capacity to generate ATP, was more sensitive to sorbic acid than its isogenic parent [31].
 

Analytical, diagnostic and therapeutic context of POTASSIUM SORBATE

  • The HPLC determination of the preservatives was performed using a reversed-phase C18 column and UV detection at 225 nm for sodium benzoate and 255 nm potassium sorbate [33].
  • Determination of sorbic acid in margarine and butter by high-performance liquid chromatography with fluorescence detection [34].
  • The inoculum effect was not caused by yeasts metabolizing or adsorbing sorbic acid, thereby lowering the effective concentration; was not due to absence of cell-cell signals in dilute cell suspensions; and was not an artefact, generated by insufficient time for small inocula to grow [35].
  • RESULTS: Topical application of 1% sorbic acid to the forearms of four human volunteers resulted in 250- to 620-fold increases in levels of PGD2 and 15- to 58-fold increases in levels of the metabolite of PGD2, 9 alpha,11 beta-PGF2, in blood drawn from the antecubital vein draining the treated sites [19].
  • Sorbic acid as well as the complexes exhibited minimum inhibitory concentrations (MICs) lower than potassium sorbate against all the strains tested [36].

References

  1. Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Downard, C.D., Roberts, L.J., Morrow, J.D. Clin. Pharmacol. Ther. (1995) [Pubmed]
  2. Value of oral provocation tests to aspirin and food additives in the routine investigation of asthma and chronic urticaria. Genton, C., Frei, P.C., Pécoud, A. J. Allergy Clin. Immunol. (1985) [Pubmed]
  3. Inhibition of type A and type B (proteolytic) Clostridium botulinum by sorbic acid. Lund, B.M., George, S.M., Franklin, J.G. Appl. Environ. Microbiol. (1987) [Pubmed]
  4. Fate of enterohemorrhagic Escherichia coli O157:H7 in apple cider with and without preservatives. Zhao, T., Doyle, M.P., Besser, R.E. Appl. Environ. Microbiol. (1993) [Pubmed]
  5. Effect of pH, temperature, and potassium sorbate on amino acid uptake in Salmonella typhimurium 7136. Tuncan, E.U., Martin, S.E. Appl. Environ. Microbiol. (1985) [Pubmed]
  6. Prolongation of the keeping quality of Mozzarella cheese by treatment with sorbate. Aly, M.E. Die Nahrung. (1996) [Pubmed]
  7. The pdr12 ABC transporter is required for the development of weak organic acid resistance in yeast. Piper, P., Mahé, Y., Thompson, S., Pandjaitan, R., Holyoak, C., Egner, R., Mühlbauer, M., Coote, P., Kuchler, K. EMBO J. (1998) [Pubmed]
  8. Chiral analysis of UV nonabsorbing compounds by capillary electrophoresis using macrocyclic antibiotics: 1. Separation of aspartic and glutamic acid enantiomers. Bednar, P., Aturki, Z., Stransky, Z., Fanali, S. Electrophoresis (2001) [Pubmed]
  9. Penta- and hexadienoic acid derivatives: a novel series of 5-lipoxygenase inhibitors. Malleron, J.L., Roussel, G., Gueremy, G., Ponsinet, G., Robin, J.L., Terlain, B., Tissieres, J.M. J. Med. Chem. (1990) [Pubmed]
  10. Effects of weak acids, UV and proton motive force inhibitors on pyrazinamide activity against Mycobacterium tuberculosis in vitro. Wade, M.M., Zhang, Y. J. Antimicrob. Chemother. (2006) [Pubmed]
  11. The weak acid preservative sorbic acid inhibits conidial germination and mycelial growth of Aspergillus niger through intracellular acidification. Plumridge, A., Hesse, S.J., Watson, A.J., Lowe, K.C., Stratford, M., Archer, D.B. Appl. Environ. Microbiol. (2004) [Pubmed]
  12. Effect of processing variables on the outgrowth of Clostridium sporogenes PA 3679 spores in comminuted meat cured with sorbic acid and sodium nitrite. Robach, M.C. Appl. Environ. Microbiol. (1979) [Pubmed]
  13. Effect of sorbic acid feeding on peroxisomes and sorboyl-CoA metabolizing enzymes in mouse liver. Selective induction of 2,4-dienoyl-CoA hydratase. Nishimaki-Mogami, T., Tanaka, A., Minegishi, K., Takahashi, A. Biochem. Pharmacol. (1991) [Pubmed]
  14. Synthesis and absolute configuration of lactone II isolated from Streptomyces sp. Go 40/10. Ueki, T., Morimoto, Y., Kinoshita, T. Chem. Commun. (Camb.) (2001) [Pubmed]
  15. Effects of potassium sorbate and other antibotulinal agents on germination and outgrowth of Clostridium botulinum type E spores in microcultures. Seward, R.A., Deibel, R.H., Lindsay, R.C. Appl. Environ. Microbiol. (1982) [Pubmed]
  16. An animal model for nonimmunologic contact urticaria. Lahti, A., Maibach, H.I. Toxicol. Appl. Pharmacol. (1984) [Pubmed]
  17. Influence of metabolic and physical factors on production of diacetoxyscirpenol by Fusarium sambucinum Fuckel. Monnet, D., Vidal, D., Créach, O. Appl. Environ. Microbiol. (1988) [Pubmed]
  18. Growth inhibition of putrefactive anaerobe 3679 caused by stringent-type response induced by protonophoric activity of sorbic acid. Ronning, I.E., Frank, H.A. Appl. Environ. Microbiol. (1987) [Pubmed]
  19. Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid. Morrow, J.D., Minton, T.A., Awad, J.A., Roberts, L.J. Archives of dermatology. (1994) [Pubmed]
  20. A 12-month, multicenter, randomized, double-masked, parallel-group comparison of timolol-LA once daily and timolol maleate ophthalmic solution twice daily in the treatment of adults with glaucoma or ocular hypertension. Mundorf, T.K., Ogawa, T., Naka, H., Novack, G.D., Crockett, R.S. Clinical therapeutics. (2004) [Pubmed]
  21. Cellular lipid composition influences stress activation of the yeast general stress response element (STRE). Chatterjee, M.T., Khalawan, S.A., Curran, B.P. Microbiology (Reading, Engl.) (2000) [Pubmed]
  22. Sorbic acid-induced erythema and edema. Soschin, D., Leyden, J.J. J. Am. Acad. Dermatol. (1986) [Pubmed]
  23. Evaluation of 1,3-pentadiene for mutagenicity by the Salmonella/mammalian microsome assay. Liewen, M.B., Marth, E.H. Mutat. Res. (1985) [Pubmed]
  24. Depletion of the reduced glutathione level in the liver and production of the mutagens in the intestine in the mice inducing hepatoma by feeding on a high level dose of sorbic acid. Tsuchiya, T., Yamaha, T. Mutat. Res. (1984) [Pubmed]
  25. Effects of sorbic acid and sorbic acid-nitrite in vivo on bone marrow chromosomes of mice. Banerjee, T.S., Giri, A.K. Toxicol. Lett. (1986) [Pubmed]
  26. Modeling yeast spoilage in cold-filled ready-to-drink beverages with Saccharomyces cerevisiae, Zygosaccharomyces bailii, and Candida lipolytica. Battey, A.S., Duffy, S., Schaffner, D.W. Appl. Environ. Microbiol. (2002) [Pubmed]
  27. Inhibition by antimicrobial food additives of ochratoxin A production by Aspergillus sulphureus and Penicillium viridicatum. Tong, C.H., Draughon, F.A. Appl. Environ. Microbiol. (1985) [Pubmed]
  28. A novel antibiofilm technology for contact lens solutions. Farber, B.F., Hsieh, H.C., Donnenfeld, E.D., Perry, H.D., Epstein, A., Wolff, A. Ophthalmology (1995) [Pubmed]
  29. Stimulation of aflatoxin B1 and T-2 toxin production by sorbic acid. Gareis, M., Bauer, J., von Montgelas, A., Gedek, B. Appl. Environ. Microbiol. (1984) [Pubmed]
  30. The yeast model for batten disease: mutations in BTN1, BTN2, and HSP30 alter pH homeostasis. Chattopadhyay, S., Muzaffar, N.E., Sherman, F., Pearce, D.A. J. Bacteriol. (2000) [Pubmed]
  31. Activity of the plasma membrane H(+)-ATPase and optimal glycolytic flux are required for rapid adaptation and growth of Saccharomyces cerevisiae in the presence of the weak-acid preservative sorbic acid. Holyoak, C.D., Stratford, M., McMullin, Z., Cole, M.B., Crimmins, K., Brown, A.J., Coote, P.J. Appl. Environ. Microbiol. (1996) [Pubmed]
  32. Parallel and comparative analysis of the proteome and transcriptome of sorbic acid-stressed Saccharomyces cerevisiae. de Nobel, H., Lawrie, L., Brul, S., Klis, F., Davis, M., Alloush, H., Coote, P. Yeast (2001) [Pubmed]
  33. Rapid high-performance liquid chromatography method for the analysis of sodium benzoate and potassium sorbate in foods. Pylypiw, H.M., Grether, M.T. Journal of chromatography. A. (2000) [Pubmed]
  34. Determination of sorbic acid in margarine and butter by high-performance liquid chromatography with fluorescence detection. Burini, G., Damiani, P. J. Chromatogr. (1991) [Pubmed]
  35. Sorbic acid resistance: the inoculum effect. Steels, H., James, S.A., Roberts, I.N., Stratford, M. Yeast (2000) [Pubmed]
  36. Controlled release of water-soluble polymeric complexes of sorbic acid with antifungal activities. Charvalos, E., Tzatzarakis, M., Tsatsakis, A., Petrikkos, G. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
 
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