Meconic acid

Meconic acid
IUPAC name 3-Hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid
Identifiers
CAS number	497-59-6
PubChem	5351448
Jmol-3D images	Image 1
SMILES C1=C(OC(=C(O)O)C(=O)C1=O)C(=O)O
Properties
Molecular formula	C7H4O7
Molar mass	200.10
Appearance	colorless crystals
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Meconic acid, also known as acidum meconicum and poppy acid, is a chemical substance found in certain plants of the Papaveraceae family (poppy) 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.

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.

See also

• Opium
• Muconic acid, an unrelated dicarboxylic acid

References

• Scott Lovell, Paramjeet Subramony, and Bart Kahr (1999). "Poppy Acid: Synthesis and Crystal Chemistry". J. Am. Chem. Soc. 121 (30): 7020–7025. doi:10.1021/ja990402a.