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
Identifiers
CAS Number	88-21-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1015;
ChemSpider	6660;
ECHA InfoCard	100.001.646
EC Number	201-810-9;
KEGG	C06333 ;
PubChem CID	6926;
UNII	ZB9JSA4BH0 ;
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
Acidity (pKa)	2.46 (H2O)
	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

^ "PubChem entry". Retrieved 2014-05-17.
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

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[1] "PubChem entry". Retrieved 2014-05-17.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.

[Kale-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.

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