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Chemical Compound Review

pOH-Ph-CH2CHO     2-(4-hydroxyphenyl)ethanal

Synonyms: AG-L-64027, CHEBI:15621, HMDB03767, ANW-61912, AK-77585, ...
 
 
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Disease relevance of HYDROXYACETOPHENONE

 

High impact information on HYDROXYACETOPHENONE

 

Biological context of HYDROXYACETOPHENONE

  • Molecular modeling studies were carried out by a combined use of conformational analysis and 3D-QSAR methods of identify molecular features common to a series of hydroxyacetophenone (HAP) and non-hydroxyacetophenone (non-HAP) peptide leukotriene (pLT) receptor antagonists [7].
 

Anatomical context of HYDROXYACETOPHENONE

  • The present study examined whether VLDL modification by the reactive aldehyde p-hydroxyphenylacetaldehyde (pHA) enhances cholesteryl ester (CE) accumulation by J774A.1 macrophages. pHA is the major product derived from the oxidation of L-tyrosine by myeloperoxidase and is a component of human atherosclerotic lesions [8].
  • Based on different choleretic activities of hydroxyacetophenone analogues including 4-mono; 2,6-di and 2,4,6-trihydroxy-acetophenone (MHA, DHA and THA), the present study aims to determine if these compounds stimulated vesicular transport in hepatocytes [2].
 

Associations of HYDROXYACETOPHENONE with other chemical compounds

 

Analytical, diagnostic and therapeutic context of HYDROXYACETOPHENONE

References

  1. Conversion of (+/-)-synephrine into p-hydroxyphenylacetaldehyde by Arthrobacter synephrinum. A novel enzymic reaction. Veeraswamy, M., Devi, N.A., Kutty, R.K., Rao, P.V. Biochem. J. (1976) [Pubmed]
  2. Differential effects of hydroxyacetophenone analogues on the transcytotic vesicular pathway in rat liver. Tradtrantip, L., Boyer, J.L., Suksamrarn, A., Piyachaturawat, P. Eur. J. Pharmacol. (2006) [Pubmed]
  3. 2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. Halkier, B.A., Lykkesfeldt, J., Møller, B.L. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  4. p-Hydroxyphenylacetaldehyde, the major product of L-tyrosine oxidation by the myeloperoxidase-H2O2-chloride system of phagocytes, covalently modifies epsilon-amino groups of protein lysine residues. Hazen, S.L., Gaut, J.P., Hsu, F.F., Crowley, J.R., d'Avignon, A., Heinecke, J.W. J. Biol. Chem. (1997) [Pubmed]
  5. p-Hydroxyphenylacetaldehyde is the major product of L-tyrosine oxidation by activated human phagocytes. A chloride-dependent mechanism for the conversion of free amino acids into reactive aldehydes by myeloperoxidase. Hazen, S.L., Hsu, F.F., Heinecke, J.W. J. Biol. Chem. (1996) [Pubmed]
  6. Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. Sibbesen, O., Koch, B., Halkier, B.A., Møller, B.L. J. Biol. Chem. (1995) [Pubmed]
  7. A proposed common spatial pharmacophore and the corresponding active conformations of some peptide leukotriene receptor antagonists. Hariprasad, V., Kulkarni, V.M. J. Comput. Aided Mol. Des. (1996) [Pubmed]
  8. Modification of type III VLDL, their remnants, and VLDL from ApoE-knockout mice by p-hydroxyphenylacetaldehyde, a product of myeloperoxidase activity, causes marked cholesteryl ester accumulation in macrophages. Whitman, S.C., Hazen, S.L., Miller, D.B., Hegele, R.A., Heinecke, J.W., Huff, M.W. Arterioscler. Thromb. Vasc. Biol. (1999) [Pubmed]
  9. Elevated levels of protein-bound p-hydroxyphenylacetaldehyde, an amino-acid-derived aldehyde generated by myeloperoxidase, are present in human fatty streaks, intermediate lesions and advanced atherosclerotic lesions. Hazen, S.L., Gaut, J.P., Crowley, J.R., Hsu, F.F., Heinecke, J.W. Biochem. J. (2000) [Pubmed]
  10. Metabolism of amines in the isolated perfused mesenteric arterial bed of the rat. Elliott, J., Callingham, B.A., Sharman, D.F. Br. J. Pharmacol. (1989) [Pubmed]
  11. Spiroiminodihydantoin is a major product in the photooxidation of 2'-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis. Adam, W., Arnold, M.A., Grüne, M., Nau, W.M., Pischel, U., Saha-Möller, C.R. Org. Lett. (2002) [Pubmed]
  12. The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench. Halkier, B.A., Olsen, C.E., Møller, B.L. J. Biol. Chem. (1989) [Pubmed]
 
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