Chloroacetic acid
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MedKoo CAT#: 558629

CAS#: 79-11-8

Description: Chloroacetic acid is a chlorinated analog of acetic acid. It induces neuronal cells death through oxidative stress-mediated p38-MAPK activation pathway.

Chemical Structure

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Chloroacetic acid
CAS# 79-11-8
Instruction

Theoretical Analysis

MedKoo Cat#: 558629
Name: Chloroacetic acid
CAS#: 79-11-8
Chemical Formula: C2H3ClO2
Exact Mass: 93.98
Molecular Weight: 94.490
Elemental Analysis: C, 25.42; H, 3.20; Cl, 37.52; O, 33.86

Price and Availability

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25g USD 350 2 Weeks
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Synonym: Chloroacetic acid; Chloroethanoic acid; Monochloracetic acid;

IUPAC/Chemical Name: Acetic acid, 2-chloro-

InChi Key: FOCAUTSVDIKZOP-UHFFFAOYSA-N

InChi Code: InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

SMILES Code: O=C(O)CCl

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:

Preparing Stock Solutions

The following data is based on the product molecular weight 94.49 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.

Recalculate based on batch purity %
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:

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1: Lu TH, Su CC, Tang FC, Chen CH, Yen CC, Fang KM, Lee kI, Hung DZ, Chen YW. Chloroacetic acid triggers apoptosis in neuronal cells via a reactive oxygen species-induced endoplasmic reticulum stress signaling pathway. Chem Biol Interact. 2015 Jan 5;225:1-12. doi: 10.1016/j.cbi.2014.10.022. Epub 2014 Oct 29. PubMed PMID: 25451595.

2: Tang S, Yang HW, Wang XM, Xie YF. [Influencing factors and reaction mechanism of chloroacetic acid reduction by cast iron]. Huan Jing Ke Xue. 2014 Mar;35(3):972-8. Chinese. PubMed PMID: 24881385.

3: Chen CH, Chen SJ, Su CC, Yen CC, Tseng TJ, Jinn TR, Tang FC, Chen KL, Su YC, Lee kI, Hung DZ, Huang CF. Chloroacetic acid induced neuronal cells death through oxidative stress-mediated p38-MAPK activation pathway regulated mitochondria-dependent apoptotic signals. Toxicology. 2013 Jan 7;303:72-82. doi: 10.1016/j.tox.2012.10.008. Epub 2012 Oct 26. PubMed PMID: 23103613.

4: Bai Y, Zhu BL, Wang JF. [Investigation on coal work's production use of chloroacetic acid in one province]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2010 Oct;28(10):781-2. Chinese. PubMed PMID: 21126433.

5: Faisal Siddiqui M, Ahmad R, Ahmad W, Hasnain AU. Micronuclei induction and chromosomal aberrations in Rattus norvegicus by chloroacetic acid and chlorobenzene. Ecotoxicol Environ Saf. 2006 Oct;65(2):159-64. Epub 2006 May 2. PubMed PMID: 16647117.

6: Liu XD, Zhao W, Pan XF, Yan HF. [Determination of thiodiglycolic acid in urine by ion chromatography with solidphase extraction]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2016 Apr 20;34(4):297-9. doi: 10.3760/cma.j.issn.1001-9391.2016.04.017. Chinese. PubMed PMID: 27514269.

7: Bruggink SC, Gussekloo J, Egberts PF, Bavinck JNB, de Waal MWM, Assendelft WJJ, Eekhof JAH. Monochloroacetic acid application is an effective alternative to cryotherapy for common and plantar warts in primary care: a randomized controlled trial. J Invest Dermatol. 2015 May;135(5):1261-1267. doi: 10.1038/jid.2015.1. Epub 2015 Feb 5. PubMed PMID: 25584800.

8: Clark JS, Romiti F, Hogg KF, Hamid MH, Richter SC, Boyer A, Redman JC, Farrugia LJ. Synthesis of cyclopropyl-substituted furans by brønsted Acid promoted cascade reactions. Angew Chem Int Ed Engl. 2015 May 4;54(19):5744-7. doi: 10.1002/anie.201500625. Epub 2015 Mar 17. PubMed PMID: 25782604.

9: Luo X, Chen L, Zhao Y. Simultaneous determination of three chloroacetic acids, three herbicides, and 12 anions in water by ion chromatography. J Sep Sci. 2015 Sep;38(17):3096-102. doi: 10.1002/jssc.201401456. PubMed PMID: 26147076.

10: Yu Y, Liu D, Liu C, Luo G. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst. Bioorg Med Chem Lett. 2007 Jun 15;17(12):3508-10. Epub 2006 Dec 23. PubMed PMID: 17490874.

11: SAWLEWICZ L, KURASZKIEWICZ W. [ON THE EFFECT OF CHLOROACETIC ACID ON BENZIMIDAZOLONE AND SOME OF ITS DERIVATIVES]. Acta Pol Pharm. 1963;20:413-7. Polish. PubMed PMID: 14192320.

12: Meng T, Yang M, Li YX, Jia Q, Yu GC, Dai YF. [Effect of mitogen-activated protein kinase signaling pathway on apoptosis induced by chloroacetic acid in human normal bronchial epithelial 16HBE cells]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2017 May 20;35(5):321-327. doi: 10.3760/cma.j.issn.1001-9391.2017.05.001. Chinese. PubMed PMID: 28780785.

13: Chaiken IM, Smith EL. Reaction of the sulfhydryl group of papain with chloroacetic acid. J Biol Chem. 1969 Oct 10;244(19):5095-9. PubMed PMID: 5344123.

14: Pals J, Attene-Ramos MS, Xia M, Wagner ED, Plewa MJ. Human cell toxicogenomic analysis linking reactive oxygen species to the toxicity of monohaloacetic acid drinking water disinfection byproducts. Environ Sci Technol. 2013;47(21):12514-23. doi: 10.1021/es403171b. Epub 2013 Oct 10. PubMed PMID: 24050308; PubMed Central PMCID: PMC4014314.

15: Bhat HK, Ansari GA. Covalent interaction of chloroacetic and acetic acids with cholesterol. J Biochem Toxicol. 1989 Fall;4(3):189-93. PubMed PMID: 2607543.

16: Procházka E, Escher BI, Plewa MJ, Leusch FD. In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts. Chem Res Toxicol. 2015 Oct 19;28(10):2059-68. doi: 10.1021/acs.chemrestox.5b00283. Epub 2015 Sep 18. PubMed PMID: 26327680.

17: Bhat HK, Kanz MF, Campbell GA, Ansari GA. Ninety day toxicity study of chloroacetic acids in rats. Fundam Appl Toxicol. 1991 Aug;17(2):240-53. PubMed PMID: 1765218.

18: Durlak P, Morrison CA, Middlemiss DS, Latajka Z. Car-Parrinello and path integral molecular dynamics study of the hydrogen bond in the chloroacetic acid dimer system. J Chem Phys. 2007 Aug 14;127(6):064304. PubMed PMID: 17705593.

19: Jeong CH, Gao L, Dettro T, Wagner ED, Ricke WA, Plewa MJ, Flaws JA. Monohaloacetic acid drinking water disinfection by-products inhibit follicle growth and steroidogenesis in mouse ovarian antral follicles in vitro. Reprod Toxicol. 2016 Jul;62:71-6. doi: 10.1016/j.reprotox.2016.04.028. Epub 2016 May 2. PubMed PMID: 27151372; PubMed Central PMCID: PMC4905796.

20: St-Pierre A, Krishnan K, Tardif R. Evaluation of the influence of chloroacetic acids on the pharmacokinetics of trihalomethanes in the rat. J Toxicol Environ Health A. 2003 Dec 12;66(23):2267-80. PubMed PMID: 14612337.