Mucochloric acid
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MedKoo CAT#: 558651

CAS#: 87-56-9

Description: Mucochloric acid is an organic compound that consists of a dibrominated alkene with aldehyde and carboxylic acid functional groups. It is a bacterial mutagen and genotoxic compound.


Chemical Structure

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Mucochloric acid
CAS# 87-56-9

Theoretical Analysis

MedKoo Cat#: 558651
Name: Mucochloric acid
CAS#: 87-56-9
Chemical Formula: C4H2Cl2O3
Exact Mass: 167.94
Molecular Weight: 168.96
Elemental Analysis: C, 28.44; H, 1.19; Cl, 41.96; O, 28.41

Price and Availability

Size Price Availability Quantity
25.0g USD 200.0 2 Weeks
500.0g USD 485.0 2 Weeks
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Synonym: Mucochloric acid; Dichloromalealdehydic acid; Kyselina mukochlorova;

IUPAC/Chemical Name: Acrylic acid, 2,3-dichloro-3-formyl-

InChi Key: LUMLZKVIXLWTCI-NSCUHMNNSA-N

InChi Code: InChI=1S/C4H2Cl2O3/c5-2(1-7)3(6)4(8)9/h1H,(H,8,9)/b3-2+

SMILES Code: O=C(O)/C(Cl)=C(Cl)/C=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

Preparing Stock Solutions

The following data is based on the product molecular weight 168.96 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

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1: Asplund D, Kronberg L, Sjöholm R, Munter T. Reaction of mucochloric acid with adenosine: formation of 8-(N6-adenosinyl)ethenoadenosine derivatives. Chem Res Toxicol. 1995 Sep;8(6):841-6. PubMed PMID: 7492733.

2: Politzer IR, Crago KT, Benjamin W, Joseph J, Amos K, Coleman WE. Effect of beta-cyclodextrin on mucochloric acid and 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone. Arch Environ Contam Toxicol. 1991 Apr;20(3):371-4. PubMed PMID: 1859209.

3: Jansson K, Hyttinen JM, Niittykoski M, Mäki-Paakkanen J. Mutagenicity in vitro of 3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid), a chlorine disinfection by-product in drinking water. Environ Mol Mutagen. 1995;25(4):284-7. PubMed PMID: 7607182.

4: Isomaa B, Holmström TH, Lilius H, Franzén R, Kronberg L. The toxicity of the mutagen 'MX' and its analogue, mucochloric acid, to rainbow trout hepatocytes and gill epithelial cells and to Daphnia magna. Toxicology. 1995 Jun 26;100(1-3):69-77. PubMed PMID: 7624884.

5: LaLonde RT, Xie S, Bu L. Test of chiral recognition in the Salmonella typhimurium (TA100) mutagenicity of mucochloric acid-cysteine adducts. Environ Mol Mutagen. 1993;22(3):181-7. PubMed PMID: 8404878.

6: Zhang J, Blazecka PG, Davidson JG. First direct reductive amination of mucochloric acid: a simple and efficient method for preparing highly functionalized alpha,beta-unsaturated gamma-butyrolactams. Org Lett. 2003 Feb 20;5(4):553-6. PubMed PMID: 12583767.

7: Das Sarma K, Zhang J, Curran TT. Novel synthons from mucochloric acid: the first use of alpha,beta-dichloro-gamma-butenolides and gamma-butyrolactams for direct vinylogous aldol addition. J Org Chem. 2007 Apr 27;72(9):3311-8. Epub 2007 Mar 31. PubMed PMID: 17397224.

8: Kronberg L, Karlsson S, Sjöholm R. Formation of ethenocarbaldehyde derivatives of adenosine and cytidine in reactions with mucochloric acid. Chem Res Toxicol. 1993 Jul-Aug;6(4):495-9. PubMed PMID: 8374047.

9: Kronberg L, Sjöholm R, Karlsson S. Formation of 3,N4-ethenocytidine, 1,N6-ethenoadenosine, and 1,N2-ethenoguanosine in reactions of mucochloric acid with nucleosides. Chem Res Toxicol. 1992 Nov-Dec;5(6):852-5. PubMed PMID: 1489937.

10: Steffensen IL, Paulsen JE, Engeset D, Kronberg L, Alexander J. The drinking water chlorination by-products 3,4-dichloro-5-hydroxy-2[5H]-furanone(mucochloric acid) and 3-chloro-4-(dichloromethyl)-5-hydroxy-2[5H]-furanone do not induce preneoplastic or neoplastic intestinal lesions in F344 rats, balb/ca mice or C57bl/6J-min mice. Pharmacol Toxicol. 1999 Aug;85(2):56-64. PubMed PMID: 10488686.

11: LaLonde RT, Xie S. A study of inactivation reactions of N-acetylcysteine with mucochloric acid, a mutagenic product of the chlorination of humic substances in water. Chem Res Toxicol. 1992 Sep-Oct;5(5):618-24. PubMed PMID: 1446000.

12: LaLonde RT, Xie S, Chamulitrat W, Mason RP. Oxidation and radical intermediates associated with the glutathione conjugation of mucochloric acid. Chem Res Toxicol. 1994 Jul-Aug;7(4):482-6. PubMed PMID: 7981412.

13: LaLonde RT, Ramdayal F. Mucochloric acid action on phi X174 DNA: a comparison to other chlorine-substituted 2(5H)-furanones. Chem Res Toxicol. 1997 Feb;10(2):205-10. PubMed PMID: 9049432.

14: Cooney DA, Milman HA, Jayaram HN, Homan ER. Inhibition of L-asparagine synthetase by mucochloric and mucobromic acids. Enzyme. 1976;21(6):524-39. PubMed PMID: 12938.

15: Malikova RT. [Hygienic assessment of the conditions of discharge of industrial waste resulting from the production of phenazone and mucochloric acid and substantiation of their maximum permissible concentration in bodies of water]. Gig Sanit. 1969 Dec;34(12):16-21. Russian. PubMed PMID: 5374343.

16: Kronberg L, Asplund D, Mäki J, Sjöholm R. Reaction of mucochloric and mucobromic acids with adenosine and cytidine: formation of chloro- and bromopropenal derivatives. Chem Res Toxicol. 1996 Dec;9(8):1257-63. PubMed PMID: 8951227.

17: Gómez-Bombarelli R, González-Pérez M, Calle E, Casado J. Reactivity of mucohalic acids in water. Water Res. 2011 Jan;45(2):714-20. doi: 10.1016/j.watres.2010.08.040. Epub 2010 Aug 27. PubMed PMID: 20855100.

18: Lattmann E, Sattayasai N, Schwalbe CS, Niamsanit S, Billington DC, Lattmann P, Langley CA, Singh H, Dunn S. Novel anti-bacterials against MRSA: synthesis of focussed combinatorial libraries of tri-substituted 2(5H)-furanones. Curr Drug Discov Technol. 2006 Jun;3(2):125-34. PubMed PMID: 16925520.

19: Gondela E, Walczak KZ. Synthesis and preliminary bioactivity assays of 3,4-dichloro-5-(omega-hydroxyalkylamino)-2(5H)-furanones. Eur J Med Chem. 2010 Sep;45(9):3993-7. doi: 10.1016/j.ejmech.2010.05.055. Epub 2010 Jun 2. PubMed PMID: 20573426.

20: Zhang J, Sarma KD, Curran TT, Belmont DT, Davidson JG. Efficient synthesis of novel gamma-substituted gamma-butenolides by Lewis acid catalyzed addition of metal enolates of active methylene compounds to mucohalic acids. J Org Chem. 2005 Jul 22;70(15):5890-5. PubMed PMID: 16018682.