Orthanilic acid

Orthanilic acid

Names
Preferred IUPAC name 2-Aminobenzene-1-sulfonic 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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:1015
ChemSpider	6660
ECHA InfoCard	100.001.646
EC Number	201-810-9
KEGG	C06333  N
PubChem CID	6926
UNII	ZB9JSA4BH0  Y
CompTox Dashboard (EPA)	DTXSID1024463
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
Melting point	325 °C (decomp.)
Acidity (pKa)	2.46 (H2O) [2]
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-aminobenzenesulfonic acid) 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 ^{[3] [4]} 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. ^[5]

Orthanilic acids have also been found to affect cardiac tension. ^{[6] [7]}

References

1. "PubChem entry" . Retrieved 2014-05-17.
2. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN   978-1498754286.
3. Kale, Sangram S.; Priya, Gowri; Kotmale, Amol S.; Gawade, Rupesh L.; Puranik, Vedavati G.; Rajamohanan, P. R.; Sanjayan, Gangadhar J. (March 2013). "Orthanilic acid-promoted reverse turn formation in peptides". Chem. Commun. 49 (22): 2222–4. doi:10.1039/C3CC40522B. PMID   23392615.
4. 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.
5. 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. S2CID   5778950.
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". Progress in Clinical and Biological Research. 351: 175–84. PMID   2122477.
7. 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.