Malonic acid
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MedKoo CAT#: 558655

CAS#: 141-82-2

Description: Malonic acid is a precursor and the reaction proceeds via a reactive ketene that acetylates the target amine. It has been suggested that malonic acid is a cross-linking agent between corn starch and potato starch to improve its mechanical properties.


Chemical Structure

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Malonic acid
CAS# 141-82-2

Theoretical Analysis

MedKoo Cat#: 558655
Name: Malonic acid
CAS#: 141-82-2
Chemical Formula: C3H4O4
Exact Mass: 104.01
Molecular Weight: 104.060
Elemental Analysis: C, 34.63; H, 3.87; O, 61.50

Price and Availability

Size Price Availability Quantity
25g USD 250 2 weeks
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Synonym: Malonic acid; Propanedioic acid; Kyselina malonova; Dicarboxymethane;

IUPAC/Chemical Name: malonic acid

InChi Key: OFOBLEOULBTSOW-UHFFFAOYSA-N

InChi Code: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)

SMILES Code: OC(CC(O)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 104.06 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: Chandra K, Naoum JN, Roy TK, Gilon C, Gerber RB, Friedler A. Mechanistic studies of malonic acid-mediated in situ acylation. Biopolymers. 2015 Sep;104(5):495-505. doi: 10.1002/bip.22654. PubMed PMID: 25846609.

2: Goso Y. Malonic acid suppresses mucin-type O-glycan degradation during hydrazine treatment of glycoproteins. Anal Biochem. 2016 Mar 1;496:35-42. doi: 10.1016/j.ab.2015.12.011. Epub 2015 Dec 24. PubMed PMID: 26723492.

3: Gao H, Luo Z, Ge P, He J, Zhou F, Zheng P, Jiang J. Direct Catalytic Asymmetric Synthesis of β-Hydroxy Acids from Malonic Acid. Org Lett. 2015 Dec 18;17(24):5962-5. doi: 10.1021/acs.orglett.5b02891. Epub 2015 Nov 20. PubMed PMID: 26587748.

4: Ma X, Luo X, Dochain S, Mathot C, Markò IE. Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: A Method for the Synthesis of Ketals and Ketones. Org Lett. 2015 Oct 2;17(19):4690-3. doi: 10.1021/acs.orglett.5b02084. PubMed PMID: 26392322.

5: Song CW, Kim JW, Cho IJ, Lee SY. Metabolic Engineering of Escherichia coli for the Production of 3-Hydroxypropionic Acid and Malonic Acid through β-Alanine Route. ACS Synth Biol. 2016 Nov 18;5(11):1256-1263. Epub 2016 Mar 14. PubMed PMID: 26925526.

6: Darvas M, Picaud S, Jedlovszky P. Molecular dynamics simulations of the water adsorption around malonic acid aerosol models. Phys Chem Chem Phys. 2013 Jul 14;15(26):10942-51. doi: 10.1039/c3cp50608h. Epub 2013 May 24. PubMed PMID: 23702947.

7: Nakamura S, Sano M, Toda A, Nakane D, Masuda H. Organocatalytic enantioselective decarboxylative reaction of malonic acid half thioesters with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides. Chemistry. 2015 Mar 2;21(10):3929-32. doi: 10.1002/chem.201406270. Epub 2015 Jan 22. PubMed PMID: 25614368.

8: Shibata N, Nishimine T, Shibata N, Tokunaga E, Kawada K, Kagawa T, Aceña JL, Sorochinsky AE, Soloshonok VA. Asymmetric Mannich reaction between (S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine and malonic acid derivatives. Stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids. Org Biomol Chem. 2014 Mar 7;12(9):1454-62. doi: 10.1039/c3ob42425a. PubMed PMID: 24445698.

9: Bew SP, Stephenson GR, Rouden J, Martinez-Lozano LA, Seylani H. Malonic acid half oxyesters and thioesters: solvent-free synthesis and DFT analysis of their enols. Org Lett. 2013 Aug 2;15(15):3805-7. doi: 10.1021/ol400804b. Epub 2013 Jul 22. PubMed PMID: 23876089.

10: Beyer KD, Schroeder JR, Kissinger JA. Temperature-dependent deliquescence relative humidities and water activities using humidity controlled thermogravimetric analysis with application to malonic acid. J Phys Chem A. 2014 Apr 3;118(13):2488-97. doi: 10.1021/jp412446h. Epub 2014 Mar 21. PubMed PMID: 24628358.

11: Griffin JD, Zeller MA, Nicewicz DA. Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight. J Am Chem Soc. 2015 Sep 9;137(35):11340-8. doi: 10.1021/jacs.5b07770. Epub 2015 Aug 28. PubMed PMID: 26291730; PubMed Central PMCID: PMC5768415.

12: Reddy GS, Ramkumar S, Asiri AM, Anandan S. Bi-anchoring organic sensitizers of type D-(π-A)₂ comprising thiophene-2-acetonitrile as π-spacer and malonic acid as electron acceptor for dye sensitized solar cell applications. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:531-539. doi: 10.1016/j.saa.2015.03.032. Epub 2015 Mar 9. PubMed PMID: 25801442.

13: Preska Steinberg A, Epstein IR, Dolnik M. Target Turing patterns and growth dynamics in the chlorine dioxide-iodine-malonic acid reaction. J Phys Chem A. 2014 Apr 3;118(13):2393-400. doi: 10.1021/jp500432t. Epub 2014 Mar 19. PubMed PMID: 24601764.

14: Kalonia H, Kumar P, Kumar A. Targeting oxidative stress attenuates malonic acid induced Huntington like behavioral and mitochondrial alterations in rats. Eur J Pharmacol. 2010 May 25;634(1-3):46-52. doi: 10.1016/j.ejphar.2010.02.031. Epub 2010 Feb 25. PubMed PMID: 20188726.

15: Park SY, Jeon E, Lee S, Lee J, Lee T, Won JI. An analysis of the concentration change of intermediate metabolites by gene manipulation in fatty acid biosynthesis. Enzyme Microb Technol. 2012 Jul 15;51(2):95-9. doi: 10.1016/j.enzmictec.2012.04.006. Epub 2012 Apr 27. PubMed PMID: 22664193.

16: Kumar A, Sharma N, Mishra J, Kalonia H. Synergistical neuroprotection of rofecoxib and statins against malonic acid induced Huntington's disease like symptoms and related cognitive dysfunction in rats. Eur J Pharmacol. 2013 Jun 5;709(1-3):1-12. doi: 10.1016/j.ejphar.2013.03.042. Epub 2013 Apr 3. PubMed PMID: 23562615.

17: Limwikrant W, Nagai A, Hagiwara Y, Higashi K, Yamamoto K, Moribe K. Formation mechanism of a new carbamazepine/malonic acid cocrystal polymorph. Int J Pharm. 2012 Jul 15;431(1-2):237-40. doi: 10.1016/j.ijpharm.2012.04.027. Epub 2012 Apr 16. PubMed PMID: 22537807.

18: Lafrance D, Bowles P, Leeman K, Rafka R. Mild decarboxylative activation of malonic acid derivatives by 1,1'-carbonyldiimidazole. Org Lett. 2011 May 6;13(9):2322-5. doi: 10.1021/ol200575c. Epub 2011 Apr 13. PubMed PMID: 21488674.

19: Ghosh Dastidar T, Netravali AN. 'Green' crosslinking of native starches with malonic acid and their properties. Carbohydr Polym. 2012 Nov 6;90(4):1620-8. doi: 10.1016/j.carbpol.2012.07.041. Epub 2012 Jul 22. PubMed PMID: 22944425.

20: Bauwens M, De Saint-Hubert M, Cleynhens J, Brams L, Devos E, Mottaghy FM, Verbruggen A. Radioiodinated phenylalkyl malonic acid derivatives as pH-sensitive SPECT tracers. PLoS One. 2012;7(6):e38428. doi: 10.1371/journal.pone.0038428. Epub 2012 Jun 13. PubMed PMID: 22719886; PubMed Central PMCID: PMC3374791.