WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H592261
CAS#: 88-21-1
Description: Orthanilic acid promotes reverse turn formation in peptides.
Hodoodo Cat#: H592261
Name: Orthanilic acid
CAS#: 88-21-1
Chemical Formula: C6H7NO3S
Exact Mass: 173.01
Molecular Weight: 173.186
Elemental Analysis: C, 41.61; H, 4.07; N, 8.09; O, 27.71; S, 18.51
Synonym: Orthanilic acid; NSC 147; NSC-147; NSC147
IUPAC/Chemical Name: 2-Aminobenzenesulphonic acid
InChi Key: ZMCHBSMFKQYNKA-UHFFFAOYSA-N
InChi Code: InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
SMILES Code: O=S(C1=CC=CC=C1N)(O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
More Info:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 173.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
---|---|---|---|
1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Kale SS, Kunjir SM, Gawade RL, Puranik VG, Rajamohanan PR, Sanjayan GJ. Conformational modulation of peptide secondary structures using β-aminobenzenesulfonic acid. Chem Commun (Camb). 2014 Mar 18;50(22):2886-8. doi: 10.1039/c3cc48850k. Epub 2014 Feb 3. PubMed PMID: 24487479.
2: Kale SS, Priya G, Kotmale AS, Gawade RL, Puranik VG, Rajamohanan PR, Sanjayan GJ. Orthanilic acid-promoted reverse turn formation in peptides. Chem Commun (Camb). 2013 Mar 18;49(22):2222-4. doi: 10.1039/c3cc40522b. PubMed PMID: 23392615.
3: Ruff J, Smits TH, Cook AM, Schleheck D. Identification of two vicinal operons for the degradation of 2-aminobenzenesulfonate encoded on plasmid pSAH in Alcaligenes sp. strain O-1. Microbiol Res. 2010 May 30;165(4):288-99. doi: 10.1016/j.micres.2009.05.006. Epub 2009 Jul 4. PubMed PMID: 19577910.
4: Paździor K, Klepacz-Smółka A, Ledakowicz S, Sójka-Ledakowicz J, Mrozińska Z, Zyłła R. Integration of nanofiltration and biological degradation of textile wastewater containing azo dye. Chemosphere. 2009 Apr;75(2):250-5. doi: 10.1016/j.chemosphere.2008.12.016. Epub 2009 Jan 19. PubMed PMID: 19155044.
5: Ricci L, Frosini M, Gaggelli N, Valensin G, Machetti F, Sgaragli G, Valoti M. Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues: a kinetic analysis. Biochem Pharmacol. 2006 May 14;71(10):1510-9. Epub 2006 Feb 28. PubMed PMID: 16540097.
6: Li XG, Zhang RR, Huang MR. Synthesis of electroconducting narrowly distributed nanoparticles and nanocomposite films of orthanilic acid/aniline copolymers. J Comb Chem. 2006 Mar-Apr;8(2):174-83. PubMed PMID: 16529512.
7: Zhang L, Jiang X, Niu L, Dong S. Syntheses of fully sulfonated polyaniline nano-networks and its application to the direct electrochemistry of cytochrome c. Biosens Bioelectron. 2006 Jan 15;21(7):1107-15. PubMed PMID: 15913978.
8: Tan NC, van Leeuwen A, van Voorthuizen EM, Slenders P, Prenafeta-Boldú FX, Temmink H, Lettinga G, Field JA. Fate and biodegradability of sulfonated aromatic amines. Biodegradation. 2005 Dec;16(6):527-37. PubMed PMID: 15865345.
9: Hu TL. Kinetics of azoreductase and assessment of toxicity of metabolic products from azo dyes by Pseudomonas luteola. Water Sci Technol. 2001;43(2):261-9. PubMed PMID: 11380189.
10: Mampel J, Ruff J, Junker F, Cook AM. The oxygenase component of the 2-aminobenzenesulfonate dioxygenase system from Alcaligenes sp. strain O-1. Microbiology. 1999 Nov;145 ( Pt 11):3255-64. PubMed PMID: 10589735.
11: Kreimeyer A, Müller G, Kassack M, Nickel P, Gagliardi AR. Suramin analogues with a 2-phenylbenzimidazole moiety as partial structure; potential anti HIV- and angiostatic drugs, 2: Sulfanilic acid-, benzenedisulfonic acid-, and naphthalenetrisulfonic acid analogues. Arch Pharm (Weinheim). 1998 Mar;331(3):97-103. PubMed PMID: 9557135.
12: Junker F, Leisinger T, Cook AM. 3-Sulphocatechol 2,3-dioxygenase and other dioxygenases (EC 1.13.11.2 and EC 1.14.12.-) in the degradative pathways of 2-aminobenzenesulphonic, benzenesulphonic and 4-toluenesulphonic acids in Alcaligenes sp. strain O-1. Microbiology. 1994 Jul;140 ( Pt 7):1713-22. PubMed PMID: 8075807.
13: Junker F, Field JA, Bangerter F, Ramsteiner K, Kohler HP, Joannou CL, Mason JR, Leisinger T, Cook AM. Oxygenation and spontaneous deamination of 2-aminobenzenesulphonic acid in Alcaligenes sp. strain O-1 with subsequent meta ring cleavage and spontaneous desulphonation to 2-hydroxymuconic acid. Biochem J. 1994 Jun 1;300 ( Pt 2):429-36. PubMed PMID: 8002948; PubMed Central PMCID: PMC1138180.
14: Franconi F, Bennardini F, Campana S, Failli P, Matucci R, Stendardi I, Giotti A. Effect of taurine, L-cysteic and orthanilic acids on cardiac tension. Prog Clin Biol Res. 1990;351:175-84. PubMed PMID: 2122477.
15: Thurnheer T, Zürrer D, Höglinger O, Leisinger T, Cook AM. Initial steps in the degradation of benzene sulfonic acid, 4-toluene sulfonic acids, and orthanilic acid in Alcaligenes sp. strain O-1. Biodegradation. 1990;1(1):55-64. PubMed PMID: 1368142.
16: Franconi F, Stendardi I, Failli P, Fazzini A, Giotti A. Inotropic activity of orthanilic and L-cysteic acid on isolated guinea-pig ventricular strips. Adv Exp Med Biol. 1987;217:159-65. PubMed PMID: 3124514.
17: Sulaiman ST. Determination of nitrite ion and sulfanilic and orthanilic acids by differential pulse polarography. Anal Chem. 1984 Nov;56(13):2405-7. PubMed PMID: 6517330.
18: Sturm K, Muschaweck R, Hropot M. 5-sulfamoylorthanilic acids, a sulfonamide series with salidiuretic activity. J Med Chem. 1983 Aug;26(8):1174-87. PubMed PMID: 6876086.
19: Dierickx PJ, Yde MV. In vitro interaction of aminobenzenesulfonic acids and their N-acetylated derivatives with rat liver glutathione S-transferase. Res Commun Chem Pathol Pharmacol. 1982 Sep;37(3):385-94. PubMed PMID: 7178650.