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Meconic Acid (CAS 497-59-6)

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Alternate Names:
3-Hydroxy-4-oxo-1,4-pyran-2,6-dicarboxylic Acid
CAS Number:
497-59-6
Molecular Weight:
200.1
Molecular Formula:
C7H4O7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Meconic acid is an organic compound with attention in analytical and forensic chemistry due to its association with opium. It serves as a chemical marker for the presence of opium alkaloids, as it is a unique constituent of opium poppy exudate. In analytical studies, meconic acid is used to confirm the presence of opium in various samples, which is important in legal and forensic contexts. In the field of natural products chemistry, research on meconic acid focuses on its biosynthesis within the poppy plant and its role in the plant′s defense mechanisms as a possible deterrent to herbivores and pathogens. Its chelating properties are also of interest, as it can form stable complexes with metal ions, which is relevant in the studies of metal ion transport and storage in biological systems. Additionally, meconic acid is employed in studies aimed at understanding the ecological interactions between the opium poppy and its environment, given its potential impact on soil chemistry and plant-microbe interactions.


Meconic Acid (CAS 497-59-6) References

  1. Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric analysis of opiates and metabolites in rat urine after inhalation of opium.  |  Kikura-Hanajiri, R., et al. 2003. J Chromatogr B Analyt Technol Biomed Life Sci. 789: 139-50. PMID: 12726852
  2. [Tannic acid microreactions of meconic acid alkaloids of opium and of chelidonic acid celandine alkaloids; their differentiation and application].  |  KWASNIEWSKI, V. 1952. Arch Pharm Ber Dtsch Pharm Ges. 22: 445-8. PMID: 13008442
  3. [Toxicity and effect of derivatives of meconic acid].  |  KLABUSAY, L. 1954. Cesk Farm. 3: 134-6. PMID: 13161037
  4. [Studies on gamma-pyrones. 2. On the optical properties of meconic acid derivatives].  |  EIDEN, F. 1959. Arch Pharm Ber Dtsch Pharm Ges. 292/64: 355-62. PMID: 13819689
  5. [Searches for antitubercular substances on the basis of meconic acid].  |  GORIAEV, MI. and BAZALITSKAIA, VS. 1962. Med Prom SSSR. 10: 19-22. PMID: 13949278
  6. [Gamma-Pyrone derivatives of meconic acid and maltol as specific indicators for the complexometric iron determination].  |  JUNGNICKEL, HE. and KLINGER, W. 1963. Pharmazie. 18: 128-30. PMID: 13958081
  7. Dissociation constants of certain gamma-pyrone dicarboxylic acids. Meconic acid and chelidonic acid.  |  MIYAMOTO, S. and BROCHMANN-HANSSEN, E. 1962. J Pharm Sci. 51: 552-4. PMID: 14474811
  8. The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase.  |  Pace, P., et al. 2004. Bioorg Med Chem Lett. 14: 3257-61. PMID: 15149686
  9. HCV NS5b RNA-dependent RNA polymerase inhibitors: from alpha,gamma-diketoacids to 4,5-dihydroxypyrimidine- or 3-methyl-5-hydroxypyrimidinonecarboxylic acids. Design and synthesis.  |  Summa, V., et al. 2004. J Med Chem. 47: 5336-9. PMID: 15481971
  10. Meconic acid and alkaloids in Papaver somniferum and P. bracteatum.  |  Fairbairn, JW. and Steele, MJ. 1981. Planta Med. 41: 55-60. PMID: 17401816
  11. Separation of eight alkaloids and meconic acid and quantitation of five principal alkaloids in gum opium by gradient reversed-phase high-performance liquid chromatography.  |  Ayyangar, NR. and Bhide, SR. 1988. J Chromatogr. 436: 455-65. PMID: 3360886
  12. Cytoprotective and Antioxidant Effects of Meconic Acid in Model Systems.  |  Kozin, SV., et al. 2021. Bull Exp Biol Med. 171: 619-622. PMID: 34617178
  13. Identification and quantitative determination of meconic acid by differential pulse polarography.  |  Kringstad, R., et al. 1978. Acta Pharm Suec. 15: 147-9. PMID: 676759
  14. Differentiation and comparison of raw, prepared and dross opium.  |  Lim, HY. and Kwok, SF. 1981. Bull Narc. 33: 31-41. PMID: 6913414

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Meconic Acid, 25 mg

sc-489408
25 mg
$420.00