Orthanilic acid | CAS#88-21-1 | reverse turn formation

MedKoo Cat#: 592261 | Name: Orthanilic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Orthanilic acid promotes reverse turn formation in peptides.

Chemical Structure

Orthanilic acid

CAS#88-21-1

Theoretical Analysis

MedKoo Cat#: 592261

Name: Orthanilic acid

CAS#: 88-21-1

Chemical Formula: C6H7NO3S

Exact Mass: 173.0147

Molecular Weight: 173.19

Elemental Analysis: C, 41.61; H, 4.07; N, 8.09; O, 27.71; S, 18.51

Price and Availability

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100g	USD 270.00

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Related CAS #

No Data

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

2-Aminobenzenesulfonic acid is an endogenous metabolite.

In vitro activity:

Orthanilic acid (2-aminobenzenesulfonic acid, (S)Ant), an aromatic β-amino acid, has been shown to be highly useful in inducing a folded conformation in peptides. When incorporated into peptide sequences (Xaa-(S)Ant-Yaa), this rigid aromatic β-amino acid strongly imparts a reverse-turn conformation to the peptide backbone, featuring robust 11-membered-ring hydrogen-bonding. Reference: Chem Commun (Camb). 2013 Mar 18;49(22):2222-4. https://pubmed.ncbi.nlm.nih.gov/23392615/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	33.5	193.43

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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:

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. PMID: 23392615.

In vitro protocol:

In vivo protocol:

TBD

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.