58279
Isatoic anhydride
technical, ≥94% (HPLC)
Synonym(s):
3,1-Benzoxazine-2,4(1H)-dione, Anthranilic acid N-carboxylic acid anhydride
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About This Item
Empirical Formula (Hill Notation):
C8H5NO3
CAS Number:
Molecular Weight:
163.13
Beilstein:
136786
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
Pricing and availability is not currently available.
vapor density
5.6 (vs air)
grade
technical
Assay
≥94% (HPLC)
mp
233 °C (dec.) (lit.)
SMILES string
O=C1Nc2ccccc2C(=O)O1
InChI
1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)
InChI key
TXJUTRJFNRYTHH-UHFFFAOYSA-N
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M.C. Venuti
Synthesis, 266-266 (1982)
G.M. Coppola
Synthesis, 505-505 (1980)
M H Gelb et al.
Journal of medicinal chemistry, 29(4), 585-589 (1986-04-01)
Derivatives of isatoic anhydride were prepared and tested as inhibitors of serine proteases. A number of isatoic anhydrides with positively charged substituents irreversibly inactivated several trypsin-like enzymes and preferentially inactivated trypsin over chymotrypsin. Further selectivity was obtained by introduction of
P S Gravett et al.
The International journal of biochemistry, 23(10), 1101-1110 (1991-01-01)
1. Esterase E-I from Bitis gabonica was inactivated with irreversible inhibitors which included studies with a water-soluble carbodiimide, an affinity labelling peptide and a mechanism-based inactivator. 2. The reaction with 1-ethyl-3(3-dimethylaminopropyl)-carbodiimide was biphasic and the dominant part followed saturation kinetics.
Jonathan J Goodall et al.
Chembiochem : a European journal of chemical biology, 3(1), 68-75 (2007-06-27)
The acyl-enzyme formed upon acylation of alpha-chymotrypsin with isatoic anhydride has been characterised by infrared spectroscopy. Acylation at pH 7 to yield the 2-aminobenzoyl-enzyme is rapid (k = 5.57x 10(-2)s(-1)), while deacylation is much slower (k =3.7 x 10(-5)10(-2) (s-).
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