Meconic acid

Meconic acid, also known as acidum meconicum and poppy acid, is a chemical substance found in certain plants of the poppy family, Papaveraceae, such as Papaver somniferum (opium poppy) and Papaver bracteatum. Meconic acid constitutes about 5% of opium and can be used as an analytical marker for the presence of opium. Meconic acid has erroneously been described as a mild narcotic, but it has little or no physiological activity, and is not used medicinally. Meconic acid forms salts with alkaloids and metals. These salts as well as meconic acid esters are called meconates. Meconic acid was first isolated by Friedrich Sertürner in 1805.[1]

Not to be confused with muconic acid.
Meconic acid
Names
Preferred IUPAC name
3-Hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.136
EC Number
  • 207-848-2
KEGG
MeSH C010603
UNII
  • InChI=1S/C7H4O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1,9H,(H,10,11)(H,12,13) ☒N
    Key: ZEGRKMXCOCRTCS-UHFFFAOYSA-N ☒N
  • InChI=1/C7H4O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1,9H,(H,10,11)(H,12,13)
    Key: ZEGRKMXCOCRTCS-UHFFFAOYAE
  • C1=C(OC(=C(O)O)C(=O)C1=O)C(=O)O
Properties
C7H4O7
Molar mass 200.102 g·mol−1
Appearance colorless crystals
Related compounds
Related compounds
 Chelidonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chemistry

Meconic acid is a dicarboxylic acid. Its structure contains two carboxylic acid groups (-COOH) and one keto group (=O) attached to a pyran ring. Meconic acid gives a red color with ferric chloride. Meconic acid is colorless and is only slightly soluble in water but readily soluble in alcohol.

References
  1. Friedrich Sertürner (1805) (Untitled letter to the editor), Journal der Pharmacie für Aerzte, Apotheker und Chemisten (Journal of Pharmacy for Physicians, Apothecaries, and Chemists), 13 : 229–243. See also: Sertuerner (1817) "Ueber das Morphium, eine neue salzfähige Grundlage, und die Mekonsäure, als Hauptbestandtheile des Opiums" (On morphine, a new salifiable [i.e., precipitable], fundamental substance, and meconic acid, as principal components of opium), Annalen der Physik, 55 : 56–89.
  • Scott Lovell; Paramjeet Subramony & Bart Kahr (1999). "Poppy Acid: Synthesis and Crystal Chemistry". J. Am. Chem. Soc. 121 (30): 7020–7025. doi:10.1021/ja990402a.
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