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MedKoo Cat#: 558651 | Name: Mucochloric acid
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Description:

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

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

Mucochloric acid
Mucochloric acid
CAS#87-56-9

Theoretical Analysis

MedKoo Cat#: 558651

Name: Mucochloric acid

CAS#: 87-56-9

Chemical Formula: C4H2Cl2O3

Exact Mass: 167.9381

Molecular Weight: 168.96

Elemental Analysis: C, 28.44; H, 1.19; Cl, 41.96; O, 28.41

Price and Availability

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25g USD 200.00
500g USD 485.00
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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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
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.
In vitro activity:
The present study reports the design and synthesis of N-alkyl- and N-aryl 3,4 dichloro- and 3,4-dibromopyrrole-2-one derivatives through the reductive amination of mucochloric and mucobromic acid with aliphatic and aromatic amines. The quorum sensing inhibition (QSI) activity of the synthesized compounds was determined against a P. aeruginosa MH602 reporter strain. The phenolic compounds exhibited the best activity with 80% and 75% QSI at 250 µM and were comparable in activity to the positive control compound Fu-30. Computational docking studies performed using the LasR receptor protein of P. aeruginosa suggested the importance of hydrogen bonding and hydrophobic interactions for QSI. Reference: Molecules. 2018 May 7;23(5):1106. https://pubmed.ncbi.nlm.nih.gov/29735954/
In vivo activity:
Arylated 5-hydroxy-pyrrol-2-ones were prepared in 2 synthetic steps from mucochloric acid and optimised as CCK2-selective ligands using radiolabelled binding assays. DSS (dextran sulfate sodium)-induced inflammation was analysed for derivative 7 and PNB-001 with L-365,260 as a standard. Subsequent in vivo evaluation in rats confirmed anti-inflammatory activity with respect to IBD assays. Reference: Medchemcomm. 2017 Feb 17;8(3):680-685. https://pubmed.ncbi.nlm.nih.gov/30108786/

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
Formulation protocol:
1. Almohaywi B, Taunk A, Wenholz DS, Nizalapur S, Biswas NN, Ho KKK, Rice SA, Iskander G, Black DS, Griffith R, Kumar N. Design and Synthesis of Lactams Derived from Mucochloric and Mucobromic Acids as Pseudomonas aeruginosa Quorum Sensing Inhibitors. Molecules. 2018 May 7;23(5):1106. doi: 10.3390/molecules23051106. PMID: 29735954; PMCID: PMC6100351. 2. Byczek-Wyrostek A, Kitel R, Rumak K, Skonieczna M, Kasprzycka A, Walczak K. Simple 2(5H)-furanone derivatives with selective cytotoxicity towards non-small cell lung cancer cell line A549 - Synthesis, structure-activity relationship and biological evaluation. Eur J Med Chem. 2018 Apr 25;150:687-697. doi: 10.1016/j.ejmech.2018.03.021. Epub 2018 Mar 10. PMID: 29571156. 3. Lattmann E, Sattayasai J, Narayanan R, Ngoc N, Burrell D, Balaram PN, Palizdar T, Lattmann P. Cholecystokinin-2/gastrin antagonists: 5-hydroxy-5-aryl-pyrrol-2-ones as anti-inflammatory analgesics for the treatment of inflammatory bowel disease. Medchemcomm. 2017 Feb 17;8(3):680-685. doi: 10.1039/c6md00707d. PMID: 30108786; PMCID: PMC6072330.
In vitro protocol:
1. Almohaywi B, Taunk A, Wenholz DS, Nizalapur S, Biswas NN, Ho KKK, Rice SA, Iskander G, Black DS, Griffith R, Kumar N. Design and Synthesis of Lactams Derived from Mucochloric and Mucobromic Acids as Pseudomonas aeruginosa Quorum Sensing Inhibitors. Molecules. 2018 May 7;23(5):1106. doi: 10.3390/molecules23051106. PMID: 29735954; PMCID: PMC6100351. 2. Byczek-Wyrostek A, Kitel R, Rumak K, Skonieczna M, Kasprzycka A, Walczak K. Simple 2(5H)-furanone derivatives with selective cytotoxicity towards non-small cell lung cancer cell line A549 - Synthesis, structure-activity relationship and biological evaluation. Eur J Med Chem. 2018 Apr 25;150:687-697. doi: 10.1016/j.ejmech.2018.03.021. Epub 2018 Mar 10. PMID: 29571156.
In vivo protocol:
1. Lattmann E, Sattayasai J, Narayanan R, Ngoc N, Burrell D, Balaram PN, Palizdar T, Lattmann P. Cholecystokinin-2/gastrin antagonists: 5-hydroxy-5-aryl-pyrrol-2-ones as anti-inflammatory analgesics for the treatment of inflammatory bowel disease. Medchemcomm. 2017 Feb 17;8(3):680-685. doi: 10.1039/c6md00707d. PMID: 30108786; PMCID: PMC6072330.
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.