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
3D model (JSmol)
ChemSpider
KEGG
UNII
  • 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
  • c1c(cc(=O)oc1C(=O)O)C[C@@H](C(=O)O)N
Properties
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
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

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

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.

References

  1. ↑ Hattori, S.; Komamine, A. (1959). "Stizolobic Acid: a New Amino-Acid in Stizolobium hassjoo". Nature. 183 (4668): 1116. Bibcode:1959Natur.183.1116H. doi:10.1038/1831116a0. S2CID 4219696.
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