Meconic acid

Not to be confused with muconic acid.

Meconic acid

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Names
IUPAC name 3-Hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid
Identifiers
CAS Number	497-59-6 Y
ChemSpider	10465112 N
EC Number	207-848-2
Jmol 3D model	Interactive image
KEGG	C20209 N
MeSH	C010603
PubChem	5351448
InChI 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
SMILES C1=C(OC(=C(O)O)C(=O)C1=O)C(=O)O
Properties
Chemical formula	C7H4O7
Molar mass	200.10 g·mol−1
Appearance	colorless crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.