Stizolobic acid

Stizolobic acid is an amino acid found in the sap epicotyl tips of etiolated seedlings of Stizolobium hassjoo - Mucuna pruriens.^[1]

Stizolobic acid

Names
IUPAC name 4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid
Systematic IUPAC name 4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid
Identifiers
CAS Number	15911-87-2 Y
3D model (JSmol)	Interactive image
ChemSpider	141574
KEGG	C06047
PubChem CID	161158
UNII	QXP0P9096P Y
CompTox Dashboard (EPA)	DTXSID90166588
InChI InChI=1/C9H9NO6/c10-5(8(12)13)1-4-2-6(9(14)15)16-7(11)3-4/h2-3,5H,1,10H2,(H,12,13)(H,14,15)/t5-/m0/s1
SMILES c1c(cc(=O)oc1C(=O)O)C[C@@H](C(=O)O)N
Properties
Chemical formula	C9H9NO6
Molar mass	227.172 g·mol−1
Density	1.604 g/cm3
Melting point	304.65 °C (580.37 °F; 577.80 K)
Boiling point	528.25 °C (982.85 °F; 801.40 K) at 760 mmHg
Solubility in water	2.634e+005 mg/L
Vapor pressure	1.44E-12 mmHg
Hazards
Flash point	273.2 °C (523.8 °F; 546.3 K)
Related compounds
Other anions	stizolobinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Biosynthesis

Stizolobium hassjoo catalyzes the conversion of L-dihydroxyphenylalanine into stizolobinic acid, alpha-amino-6-carboxy-2-oxo-2H-pyran-3-propionic acid, and stizolobic acid, alpha-amino-6-carboxy-2-oxo-2H-pyran-4-propionic acid, in the presence of NADP+ or NAD+ under aerobic conditions.