Mercaptoacetic acid | CAS#68-11-1 | protecting agent

MedKoo Cat#: 558648 | Name: Mercaptoacetic acid

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Description:

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

Mercaptoacetic acid is a protecting agent for tryptophan in amino acid analysis and indicator of acidicty. It is an intermediate in the chemical reactions such as addition, elimination and cyclization. It acts as a precursor to ammonium thioglycolate, sodium thioglycolate and calcium thioglycolate.

Chemical Structure

Mercaptoacetic acid

CAS#68-11-1

Theoretical Analysis

MedKoo Cat#: 558648

Name: Mercaptoacetic acid

CAS#: 68-11-1

Chemical Formula: C2H4O2S

Exact Mass: 91.9932

Molecular Weight: 92.11

Elemental Analysis: C, 26.08; H, 4.38; O, 34.74; S, 34.81

Price and Availability

Size	Price	Availability	Quantity
25g	USD 250.00	2 weeks

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Synonym

Mercaptoacetic acid; Thioglycolate; Thioglycolic acid; Thioglycollic acid; Thiovanic acid;

IUPAC/Chemical Name

Acetic acid, 2-mercapto-

InChi Key

CWERGRDVMFNCDR-UHFFFAOYSA-N

InChi Code

InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)

SMILES Code

O=C(O)CS

Appearance

Liquid

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:

Mercaptoacetic acid is a protecting agent for tryptophan in amino acid analysis and indicator of acidicty.

In vitro activity:

Zirconium oxide (ZrO2) nanoparticles were introduced onto cellulose nanofibers after being covalently functionalized with mercaptoacetic acid. The Hg(ii) selectivity is primarily due to the Lewis soft-soft acid-base chelation of Hg(ii) with the mercapto functionalities of the adsorbent. The experimental observations depict a high sorption capacity of 280.5 mg g-1 for Hg(ii). Reference: RSC Adv. 2022 Dec 14;12(55):35712-35721. https://pubmed.ncbi.nlm.nih.gov/36545069/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 92.11 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:

1. Ahmad H, Khan RA, Alsalme A. Covalently linked mercaptoacetic acid on ZrO2 coupled cellulose nanofibers for solid phase extraction of Hg(ii): experimental and DFT studies. RSC Adv. 2022 Dec 14;12(55):35712-35721. doi: 10.1039/d2ra05436a. PMID: 36545069; PMCID: PMC9748646. 2. da Silva Santos J, Junior JJ, da Silva FM. Solvent-free MALI-MGRE procedure for synthesizing 1,4-thiazolidin-4-one MALI (Mercaptoacetic Acid Looking Imine) ¬ MGRE (Mechanical Grinding Reaction Equipament). Curr Org Synth. 2022 Apr 14. doi: 10.2174/1570179419666220414112340. Epub ahead of print. PMID: 35430995.

In vitro protocol:

In vivo protocol:

TBD

1: Alkilany AM, Abulateefeh SR, Mills KK, Yaseen AI, Hamaly MA, Alkhatib HS, Aiedeh KM, Stone JW. Colloidal stability of citrate and mercaptoacetic acid capped gold nanoparticles upon lyophilization: effect of capping ligand attachment and type of cryoprotectants. Langmuir. 2014 Nov 25;30(46):13799-808. doi: 10.1021/la504000v. Epub 2014 Nov 12. PubMed PMID: 25356538. 2: Wageh S, Maize M, Donia AM, Al-Ghamdi AA, Umar A. Synthesis and Characterization of Mercaptoacetic Acid Capped Cadmium Sulphide Quantum Dots. J Nanosci Nanotechnol. 2015 Dec;15(12):9861-7. PubMed PMID: 26682425. 3: Tang W, Fan J, He Y, Huang B, Liu H, Pang D, Xie Z. The cadmium-mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots. Int J Nanomedicine. 2012;7:2631-40. doi: 10.2147/IJN.S32029. Epub 2012 May 24. PubMed PMID: 22679373; PubMed Central PMCID: PMC3368512. 4: Wageh S, Higazy AA, Al-Ghamdi AA, Hassouna AS. Effect of environment on the preparation of CdSe quantum dots capped with mercaptoacetic acid. J Nanosci Nanotechnol. 2014 Aug;14(8):6442-51. PubMed PMID: 25936134. 5: Lai JY. Biodegradable in situ gelling delivery systems containing pilocarpine as new antiglaucoma formulations: effect of a mercaptoacetic acid/N-isopropylacrylamide molar ratio. Drug Des Devel Ther. 2013 Oct 24;7:1273-85. doi: 10.2147/DDDT.S53759. eCollection 2013. PubMed PMID: 24187486; PubMed Central PMCID: PMC3810330. 6: Ren J, Yu Y, Dai F, Meng M, Zhang J, Zheng L, Hu T. Domain-confined catalytic soot combustion over Co3O4 anchored on a TiO2 nanotube array catalyst prepared by mercaptoacetic acid induced surface-grafting. Nanoscale. 2013 Dec 21;5(24):12144-9. doi: 10.1039/c3nr03757f. PubMed PMID: 24177172. 7: Payne DJ, Bateson JH, Gasson BC, Proctor D, Khushi T, Farmer TH, Tolson DA, Bell D, Skett PW, Marshall AC, Reid R, Ghosez L, Combret Y, Marchand-Brynaert J. Inhibition of metallo-beta-lactamases by a series of mercaptoacetic acid thiol ester derivatives. Antimicrob Agents Chemother. 1997 Jan;41(1):135-40. PubMed PMID: 8980769; PubMed Central PMCID: PMC163674. 8: Castro JL, López-Ramírez MR, Centeno SP, Otero JC. Adsorption of mercaptoacetic acid on a colloidal silver surface as investigated by Raman spectroscopy. Biopolymers. 2004 May-Jun 5;74(1-2):141-5. PubMed PMID: 15137112. 9: Acar HY, Celebi S, Serttunali NI, Lieberwirth I. Development of highly stable and luminescent aqueous CdS quantum dots with the poly(acrylic acid)/mercaptoacetic acid binary coating system. J Nanosci Nanotechnol. 2009 May;9(5):2820-9. PubMed PMID: 19452936. 10: Kaale E, Leonard S, Van Schepdael A, Roets E, Hoogmartens J. Capillary electrophoresis analysis of gentamicin sulphate with UV detection after pre-capillary derivatization with 1,2-phthalic dicarboxaldehyde and mercaptoacetic acid. J Chromatogr A. 2000 Oct 20;895(1-2):67-79. PubMed PMID: 11105849. 11: GAWRON O, CHESLOCK KE. The activation of papain by arylamides of mercaptoacetic acid. Arch Biochem Biophys. 1951 Nov;34(1):38-49. PubMed PMID: 14904031. 12: DOTZAUER G, KEDING G. [Transformation of hemoglobin into porphyrin with mercaptoacetic acid]. Dtsch Z Gesamte Gerichtl Med. 1955;44(4-5):550-4. German. PubMed PMID: 13330480. 13: Miao Y, Yang P, Zhao J, Du Y, He H, Liu Y. Photodegradation of Mercaptopropionic Acid- and Thioglycollic Acid-Capped CdTe Quantum Dots in Buffer Solutions. J Nanosci Nanotechnol. 2015 Jun;15(6):4462-9. PubMed PMID: 26369066. 14: KLOTZSCHE C. [Adrenal cortical hyperplasia due to mercaptoacetic acid used in permanent wave]. Arch Toxikol. 1954;15(2):130-5. German. PubMed PMID: 13218689. 15: Bolognese A, Correale G, Manfra M, Lavecchia A, Novellino E, Barone V. Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating. Org Biomol Chem. 2004 Oct 7;2(19):2809-13. Epub 2004 Sep 3. PubMed PMID: 15455154. 16: Ulusoy N, Gürsoy A, Otük G. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco. 2001 Dec;56(12):947-52. PubMed PMID: 11829115. 17: VERKHOVTSEVA TP, LEVITOV MM. [ENZYMATIC CONVERSION OF MERCAPTOACETIC ACID AMINO DERIVATIVES IN THE BIOSYNTHESIS OF PENICILLIN]. Antibiotiki. 1964 Jul;9:583-7. Russian. PubMed PMID: 14232872. 18: Liu XL, Shi Y, Kang JS, Oelschlaeger P, Yang KW. Amino Acid Thioester Derivatives: A Highly Promising Scaffold for the Development of Metallo-β-lactamase L1 Inhibitors. ACS Med Chem Lett. 2015 Apr 23;6(6):660-4. doi: 10.1021/acsmedchemlett.5b00098. eCollection 2015 Jun 11. PubMed PMID: 26101570; PubMed Central PMCID: PMC4468392. 19: Maltas E, Ertekin B. Binding of actin to thioglycolic acid modified superparamagnetic nanoparticles for antibody conjugation. Int J Biol Macromol. 2015 Jan;72:984-9. doi: 10.1016/j.ijbiomac.2014.10.006. Epub 2014 Oct 17. PubMed PMID: 25451750. 20: Yadav S, Ahuja M, Kumar A, Kaur H. Gellan-thioglycolic acid conjugate: synthesis, characterization and evaluation as mucoadhesive polymer. Carbohydr Polym. 2014 Jan;99:601-7. doi: 10.1016/j.carbpol.2013.08.068. Epub 2013 Aug 31. PubMed PMID: 24274549.