Orthanilic acid

Orthanilic acid

Names
IUPAC name 2-aminobenzenesulfonic acid
Other names Orthanilic acid, 2-Aminobenzenesulfonic acid, o-Aminobenzenesulfonic acid, Aniline-2-sulfonic acid, 88-21-1, Aniline-o-sulfonic acid[1]
Identifiers
CAS Number	88-21-1
3D model (Jmol)	Interactive image
ChEBI	CHEBI:1015
ChemSpider	6660
ECHA InfoCard	100.001.646
EC Number	201-810-9
KEGG	C06333
PubChem	6926
InChI InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10) Key: ZMCHBSMFKQYNKA-UHFFFAOYSA-N InChI=1/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10) Key: ZMCHBSMFKQYNKA-UHFFFAOYAS
SMILES c1ccc(c(c1)N)S(=O)(=O)O
Properties
Chemical formula	C6H7NO3S
Molar mass	173.19 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Orthanilic acid (2-aminobenzenesulfonate) is a biological acid with roles in benzoate degradation and microbial metabolism in diverse environments.

Orthanilic acid promotes reverse turn formation in peptides, inducing a folded conformation ^[2][3] when incorporated into peptide sequences (Xaa-SAnt-Yaa), showing robust 11-membered-ring hydrogen-bonding.

Orthanilic acid is a structural component of some azo dyes which consequently have poor bacterial degradation.^[4]

Oorthanilic acids have also been found to affect cardiac tension.^[5][6]

References

1. "PubChem entry". Retrieved 2014-05-17.
2. "Orthanilic acid-promoted reverse turn formation in peptides". Chem. Commun. (Camb.). 49: 2222–4. March 2013. doi:10.1039/C3CC40522B. PMID 23392615.
3. Kale, Sangram S.; Priya, Gowri; Kotmale, Amol S.; Gawade, Rupesh L.; Puranik, Vedavati G.; Rajamohanan, P. R.; Sanjayan, Gangadhar J. (2013). "Orthanilic acid-promoted reverse turn formation in peptides". Chemical Communications. 49 (22): 2222–4. doi:10.1039/C3CC40522B. PMID 23392615.
4. Tan, Nico C. G.; Leeuwen, Annemarie van; Voorthuizen, Ellen M. van; Slenders, Peter; Prenafeta-Boldú, Francesc X.; Temmink, Hardy; Lettinga, Gatze; Field, Jim A. (2005). "Fate and biodegradability of sulfonated aromatic amines". Biodegradation. 16 (6): 527–37. doi:10.1007/s10532-004-6593-x. PMID 15865345.
5. Franconi, F; Bennardini, F; Campana, S; Failli, P; Matucci, R; Stendardi, I; Giotti, A (1990). "Effect of taurine, L-cysteic and orthanilic acids on cardiac tension". Progress in clinical and biological research. 351: 175–84. PMID 2122477.
6. Franconi, F; Bennardini, F; Campana, S; Failli, P; Matucci, R; Stendardi, I; Giotti, A (1990). "Effect of taurine, L-cysteic and orthanilic acids on cardiac tension". Prog. Clin. Biol. Res. 351: 175–84. PMID 2122477.