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Chemical Compound Review

Pentadecyclate     pentadecanoic acid

Synonyms: pentadecanoate, CHEMBL460025, ACMC-1C8J9, AG-D-04916, CHEBI:42504, ...
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Disease relevance of pentadecanoic acid


High impact information on pentadecanoic acid


Chemical compound and disease context of pentadecanoic acid


Biological context of pentadecanoic acid


Anatomical context of pentadecanoic acid

  • Because abnormal fatty acid metabolism and cardiac adrenergic neuronal damage are observed in ischemic myocardium, (123)I-15-(p-iodophenyl)-3-R,S-methyl pentadecanoic acid (BMIPP) and (123)I-metaiodobenzylguanidine (MIBG) have recently been proposed as useful tracers for detection of myocardial damage [17].
  • Although grain source had only minimal effects on the fatty acid composition of subcutaneous fat samples, pentadecanoic acid (15:0) was greater (P < 0.05) in fat from steers fed SM3 and Steptoe barley varieties than in fat from steers fed corn [18].
  • Myristic acid (C14:0) and pentadecanoic acid (C15:0) in plasma and erythrocyte phospholipids reached a maximum increase in plasma and erythrocyte phospholipids within 2 weeks of initiating the saturated fat-rich diet but were unchanged throughout the 8 week saturated fat diet in buccal cell phospholipids [19].
  • As the chylothorax was considered to be due to thoracic duct injury at the time of operation, lymphoscintigraphy was performed by oral administration of I-123 beta-methyl-iodophenyl pentadecanoic acid (BMIPP) [20].

Associations of pentadecanoic acid with other chemical compounds

  • On-line liquid chromatography-electrospray ionization-tandem mass spectrometry revealed rapid alpha-oxidation of palmitic acid incubated at 0 degrees C with the purified alpha-oxidation enzyme, leading to (R)-2-hydroperoxypalmitic acid as the major product together with (R)-2-hydroxypalmitic acid, 1-pentadecanal, and pentadecanoic acid [21].
  • OBJECTIVE: To determine the clinical and prognostic value of identifying metabolic abnormalities of myocardial fatty acid metabolism in idiopathic dilated cardiomyopathy using iodine-123 beta-methyl-iodophenyl pentadecanoic acid (123I BMIPP) [22].
  • The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components [23].
  • Potential application of tissue Doppler imaging to assess regional left ventricular diastolic function in patients with hypertrophic cardiomyopathy: comparison with 123I-beta-methyl iodophenyl pentadecanoic acid myocardial scintigraphy [12].
  • Impaired cardiac fatty acid uptake, assessed by the radiolabelled fatty acid analogue beta-methyl-p-iodophenyl pentadecanoic acid (I-123-BMIPP), is observed in the myocardium following acute ischaemic events, but the long-term prognostic implication has not been established [24].

Gene context of pentadecanoic acid

  • A characteristic C15/C17 ratio was found for different phospholipids and the triglyceride fraction; pentadecanoic acid was the principal odd-numbered fatty acid utilized in the assembly of complex lipids [25].

Analytical, diagnostic and therapeutic context of pentadecanoic acid


  1. Assessment of fatty acid uptake in ischemic heart disease without myocardial infarction. Tateno, M., Tamaki, N., Yukihiro, M., Kudoh, T., Hattori, N., Tadamura, E., Nohara, R., Suzuki, T., Endo, K., Konishi, J. J. Nucl. Med. (1996) [Pubmed]
  2. Efficacy of 15-(123I)-p-iodophenyl pentadecanoic acid (IPPA) in assessing myocardial metabolism in a model of reversible global ischemia. Hudon, M.P., Lyster, D.M., Jamieson, E.W., Qayumi, K.A., Kiess, M.C., Rosado, L.J., Autor, A.P., Sartori, C., Dougan, H., van den Broek, J. European journal of nuclear medicine. (1988) [Pubmed]
  3. Relationship between various parameters derived from 123I-labelled beta-methyl-branched fatty acid whole-body scintigraphy and left ventricular ejection fraction in patients with ischaemic heart disease. Matsunari, I., Saga, T., Taki, J., Akashi, Y., Wakasugi, T., Hirai, J.I., Aoyama, T., Matoba, M., Nishikawa, T., Ichiyanagi, K. Nuclear medicine communications. (1994) [Pubmed]
  4. Impaired left ventricular myocardial metabolism in patients with pulmonary hypertension detected by radionuclide imaging. Nagaya, N., Satoh, T., Ishida, Y., Uematsu, M., Hirose, Y., Okano, Y., Kyotani, S., Nakanishi, N., Katafuchi, T., Kunieda, T. Nuclear medicine communications. (1997) [Pubmed]
  5. Cardiac metabolism of 15 (p-I-123 phenyl-) pentadecanoic acid after intracoronary tracer application. Reske, S.N., Koischwitz, D., Reichmann, K., Machulla, H.J., Simon, H., Knopp, R., Winkler, C. European journal of radiology. (1984) [Pubmed]
  6. Fatty acid analogue accumulation: a marker of myocyte viability in ischemic-reperfused myocardium. Miller, D.D., Gill, J.B., Livni, E., Elmaleh, D.R., Aretz, T., Boucher, C.A., Strauss, H.W. Circ. Res. (1988) [Pubmed]
  7. Protection from obesity and insulin resistance in mice overexpressing human apolipoprotein C1. Jong, M.C., Voshol, P.J., Muurling, M., Dahlmans, V.E., Romijn, J.A., Pijl, H., Havekes, L.M. Diabetes (2001) [Pubmed]
  8. Defective fatty acid uptake in the spontaneously hypertensive rat is a primary determinant of altered glucose metabolism, hyperinsulinemia, and myocardial hypertrophy. Hajri, T., Ibrahimi, A., Coburn, C.T., Knapp, F.F., Kurtz, T., Pravenec, M., Abumrad, N.A. J. Biol. Chem. (2001) [Pubmed]
  9. Defective uptake and utilization of long chain fatty acids in muscle and adipose tissues of CD36 knockout mice. Coburn, C.T., Knapp, F.F., Febbraio, M., Beets, A.L., Silverstein, R.L., Abumrad, N.A. J. Biol. Chem. (2000) [Pubmed]
  10. Evidence for a fatty acid reductase catalyzing the synthesis of aldehydes for the bacterial bioluminescent reaction. Resolution from luciferase and dependence on fatty acids. Riendeau, D., Meighen, E. J. Biol. Chem. (1979) [Pubmed]
  11. Fatty acid myocardial imaging using 123I-beta-methyl-iodophenyl pentadecanoic acid (BMIPP): comparison of myocardial perfusion and fatty acid utilization in canine myocardial infarction (occlusion and reperfusion model). Nishimura, T., Sago, M., Kihara, K., Oka, H., Shimonagata, T., Katabuchi, T., Hayashi, M., Uehara, T., Hayashida, K., Noda, H. European journal of nuclear medicine. (1989) [Pubmed]
  12. Potential application of tissue Doppler imaging to assess regional left ventricular diastolic function in patients with hypertrophic cardiomyopathy: comparison with 123I-beta-methyl iodophenyl pentadecanoic acid myocardial scintigraphy. Yamada, H., Oki, T., Yamamoto, T., Tanaka, H., Tabata, T., Wakatsuki, T., Nomura, M., Ito, S., Thomas, J.D. Clinical cardiology. (2004) [Pubmed]
  13. Estimated intake of milk fat is negatively associated with cardiovascular risk factors and does not increase the risk of a first acute myocardial infarction. A prospective case-control study. Warensjö, E., Jansson, J.H., Berglund, L., Boman, K., Ahrén, B., Weinehall, L., Lindahl, B., Hallmans, G., Vessby, B. Br. J. Nutr. (2004) [Pubmed]
  14. Clinical value of iodine-123 beta-methyliodophenyl pentadecanoic acid (BMIPP) myocardial single photon emission computed tomography for predicting cardiac death among patients with chronic heart failure. Sasaki, R., Mitani, I., Usui, T., Kitamura, Y., Yoshii, Y., Ishikawa, T., Uchino, K., Takahashi, N., Kimura, K., Umemura, S. Circ. J. (2003) [Pubmed]
  15. Fatty acid-specific, regiospecific, and stereospecific hydroxylation by cytochrome P450 (CYP152B1) from Sphingomonas paucimobilis: substrate structure required for alpha-hydroxylation. Matsunaga, I., Sumimoto, T., Ueda, A., Kusunose, E., Ichihara, K. Lipids (2000) [Pubmed]
  16. Controlled regioselectivity of fatty acid oxidation by whole cells producing cytochrome P450BM-3 monooxygenase under varied dissolved oxygen concentrations. Schneider, S., Wubbolts, M.G., Oesterhelt, G., Sanglard, D., Witholt, B. Biotechnol. Bioeng. (1999) [Pubmed]
  17. Myocardial sympathetic denervation, fatty acid metabolism, and left ventricular wall motion in vasospastic angina. Watanabe, K., Takahashi, T., Miyajima, S., Hirokawa, Y., Tanabe, N., Kato, K., Kodama, M., Aizawa, Y., Tazawa, S., Inoue, M. J. Nucl. Med. (2002) [Pubmed]
  18. Effects of barley variety fed to steers on carcass characteristics and color of meat. Boles, J.A., Bowman, J.G., Surber, L.M., Boss, D.L. J. Anim. Sci. (2004) [Pubmed]
  19. Buccal cells as biomarkers of fat intake. Skeaff, C.M., McLachlan, K., Eyles, H., Green, T. Asia Pacific journal of clinical nutrition. (2003) [Pubmed]
  20. Localization of chyle leakage site in postoperative chylothorax by oral administration of I-123 BMIPP. Sugiura, K., Tanabe, Y., Ogawa, T., Tokushima, T. Annals of nuclear medicine. (2005) [Pubmed]
  21. A dual function alpha-dioxygenase-peroxidase and NAD(+) oxidoreductase active enzyme from germinating pea rationalizing alpha-oxidation of fatty acids in plants. Saffert, A., Hartmann-Schreier, J., Schön, A., Schreier, P. Plant Physiol. (2000) [Pubmed]
  22. Assessment of myocardial fatty acid metabolic abnormalities in patients with idiopathic dilated cardiomyopathy using 123I BMIPP SPECT: correlation with clinicopathological findings and clinical course. Yazaki, Y., Isobe, M., Takahashi, W., Kitabayashi, H., Nishiyama, O., Sekiguchi, M., Takemura, T. Heart (1999) [Pubmed]
  23. Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85. Vinogradov, E., Egbosimba, E.E., Perry, M.B., Lam, J.S., Forsberg, C.W. Eur. J. Biochem. (2001) [Pubmed]
  24. Prognostic value of impaired myocardial fatty acid uptake in patients with acute myocardial infarction. Nakata, T., Kobayashi, T., Tamaki, N., Kobayashi, H., Wakabayashi, T., Shimoshige, S., Oh-Hori, K., Hamabe, K., Hirasawa, K., Matsuki, T., Shogase, T., Furudate, M., Shimamoto, K. Nuclear medicine communications. (2000) [Pubmed]
  25. Methylmalonic and propionic acidemias: lipid profiles of normal and affected human skin fibroblasts incubated with [1-14C]propionate. Giudici, T.A., Chen, R.G., Oizumi, J., Shaw, K.N., Ng, W.G., Donnell, G.N. Biochem. Med. Metab. Biol. (1986) [Pubmed]
  26. Echocardiography and fatty acid single photon emission tomography in predicting reversibility of regional left ventricular dysfunction after coronary angioplasty. Haque, T., Furukawa, T., Yoshida, S., Maeda, K., Matsuo, S., Takahashi, M., Kinoshita, M. Eur. Heart J. (1998) [Pubmed]
  27. Metabolism of iodine-123-BMIPP in perfused rat hearts. Yamamichi, Y., Kusuoka, H., Morishita, K., Shirakami, Y., Kurami, M., Okano, K., Itoh, O., Nishimura, T. J. Nucl. Med. (1995) [Pubmed]
  28. Qualitative and quantitative analysis of peanut oil triacylglycerols by reversed-phase liquid chromatography. Sempore, G., Bezard, J. J. Chromatogr. (1986) [Pubmed]
  29. Detection of coronary microvascular disease by means of cardiac scintigraphy. Matsuo, S., Nakamura, Y., Matsumoto, T., Takahashi, M., Kinoshita, M. The Canadian journal of cardiology. (2002) [Pubmed]
  30. Comparative myocardial imaging in the baboon with 123I-labelled ortho and para isomers of 15-(iodophenyl)pentadecanoic acid (IPPA). Dormehl, I., Feinendegen, L., Hugo, N., Rossouw, N., White, A. Nuclear medicine communications. (1993) [Pubmed]
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