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MedKoo Cat#: 558631 | Name: Citraconic acid
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Description:

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

Citraconic acid is a dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.

Chemical Structure

Citraconic acid
Citraconic acid
CAS#498-23-7

Theoretical Analysis

MedKoo Cat#: 558631

Name: Citraconic acid

CAS#: 498-23-7

Chemical Formula: C5H6O4

Exact Mass: 130.0300

Molecular Weight: 130.10

Elemental Analysis: C, 46.16; H, 4.65; O, 49.19

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
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Synonym
Citraconic acid; Citraconsaeure; Kyselina citrakonova; Methyl-maleinsaeure; Methylmaleic acid;
IUPAC/Chemical Name
2-methylfumaric acid
InChi Key
HNEGQIOMVPPMNR-NSCUHMNNSA-N
InChi Code
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
SMILES Code
OC(/C=C(C)/C(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

Preparing Stock Solutions

The following data is based on the product molecular weight 130.10 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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Distinct Nrf2 Signaling Mechanisms of Fumaric Acid Esters and Their Role in Neuroprotection against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine-Induced Experimental Parkinson's-Like Disease. J Neurosci. 2016 Jun 8;36(23):6332-51. doi: 10.1523/JNEUROSCI.0426-16.2016. PubMed PMID: 27277809; PubMed Central PMCID: PMC4899530. 5: Haarmann A, Nehen M, Deiß A, Buttmann M. Fumaric Acid Esters Do Not Reduce Inflammatory NF-κB/p65 Nuclear Translocation, ICAM-1 Expression and T-Cell Adhesiveness of Human Brain Microvascular Endothelial Cells. Int J Mol Sci. 2015 Aug 13;16(8):19086-95. doi: 10.3390/ijms160819086. PubMed PMID: 26287168; PubMed Central PMCID: PMC4581287. 6: Cao J, Su T, Zhang L, Liu R, Wang G, He B, Gu Z. Polymeric micelles with citraconic amide as pH-sensitive bond in backbone for anticancer drug delivery. Int J Pharm. 2014 Aug 25;471(1-2):28-36. doi: 10.1016/j.ijpharm.2014.05.010. Epub 2014 May 13. PubMed PMID: 24836667. 7: Ye T, Wang B, Liu J, Chen J, Yang Y. Quantitative analysis of citric acid/sodium hypophosphite modified cotton by HPLC and conductometric titration. Carbohydr Polym. 2015 May 5;121:92-8. doi: 10.1016/j.carbpol.2014.12.028. Epub 2014 Dec 31. PubMed PMID: 25659676. 8: Hunziker N, Olmos L. [Basophils in the infiltrate of guinea pig experimental contact dermatitis. Dinitrochlorobenzene and citraconic anhydride (author's transl)]. Dermatologica. 1976;152(5):270-80. French. PubMed PMID: 955226. 9: Xie X, Zhao Y, Ma CY, Xu XM, Zhang YQ, Wang CG, Jin J, Shen X, Gao JL, Li N, Sun ZJ, Dong DL. Dimethyl fumarate induces necroptosis in colon cancer cells through GSH depletion/ROS increase/MAPKs activation pathway. Br J Pharmacol. 2015 Aug;172(15):3929-43. doi: 10.1111/bph.13184. Epub 2015 Jun 12. PubMed PMID: 25953698; PubMed Central PMCID: PMC4523346. 10: Bénardais K, Pul R, Singh V, Skripuletz T, Lee DH, Linker RA, Gudi V, Stangel M. Effects of fumaric acid esters on blood-brain barrier tight junction proteins. Neurosci Lett. 2013 Oct 25;555:165-70. doi: 10.1016/j.neulet.2013.09.038. Epub 2013 Sep 26. PubMed PMID: 24076006. 11: Yao Y, Miao W, Liu Z, Han W, Shi K, Shen Y, Li H, Liu Q, Fu Y, Huang D, Shi FD. Dimethyl Fumarate and Monomethyl Fumarate Promote Post-Ischemic Recovery in Mice. Transl Stroke Res. 2016 Dec;7(6):535-547. Epub 2016 Sep 10. PubMed PMID: 27614618; PubMed Central PMCID: PMC5065588. 12: Namimatsu S, Ghazizadeh M, Sugisaki Y. Reversing the effects of formalin fixation with citraconic anhydride and heat: a universal antigen retrieval method. J Histochem Cytochem. 2005 Jan;53(1):3-11. PubMed PMID: 15637333. 13: Refat MS. Preparation of manganese(II), chromium(III) and ferric(III) oxides nanoparticles in situ metal citraconate complexes frameworks. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:281-91. doi: 10.1016/j.saa.2014.05.066. Epub 2014 Jun 4. PubMed PMID: 24952090. 14: Gao HY, Yaylayan VA, Yeboah F. Oxalic acid-induced modifications of postglycation activity of lysozyme and its glycoforms. J Agric Food Chem. 2010 May 26;58(10):6219-25. doi: 10.1021/jf100479r. PubMed PMID: 20411940. 15: Rostami-Yazdi M, Clement B, Mrowietz U. Pharmacokinetics of anti-psoriatic fumaric acid esters in psoriasis patients. Arch Dermatol Res. 2010 Sep;302(7):531-8. doi: 10.1007/s00403-010-1061-4. Epub 2010 Jun 24. PubMed PMID: 20574745. 16: Leschziner G, Rudge P, Lucas S, Andrews T. Lymphomatosis cerebri presenting as a rapidly progressive dementia with a high methylmalonic acid. J Neurol. 2011 Aug;258(8):1489-93. doi: 10.1007/s00415-011-5965-5. Epub 2011 Mar 2. PubMed PMID: 21365456. 17: Gillard GO, Collette B, Anderson J, Chao J, Scannevin RH, Huss DJ, Fontenot JD. DMF, but not other fumarates, inhibits NF-κB activity in vitro in an Nrf2-independent manner. J Neuroimmunol. 2015 Jun 15;283:74-85. doi: 10.1016/j.jneuroim.2015.04.006. Epub 2015 Apr 23. PubMed PMID: 26004161. 18: Zoghi S, Amirghofran Z, Nikseresht A, Ashjazadeh N, Kamali-Sarvestani E, Rezaei N. Cytokine secretion pattern in treatment of lymphocytes of multiple sclerosis patients with fumaric acid esters. Immunol Invest. 2011;40(6):581-96. doi: 10.3109/08820139.2011.569626. Epub 2011 Apr 21. PubMed PMID: 21510778. 19: Zhang J, Yang D, Li M, Shi L. Metabolic Profiles Reveal Changes in Wild and Cultivated Soybean Seedling Leaves under Salt Stress. PLoS One. 2016 Jul 21;11(7):e0159622. doi: 10.1371/journal.pone.0159622. eCollection 2016. PubMed PMID: 27442489; PubMed Central PMCID: PMC4956222. 20: Peng H, Li H, Sheehy A, Cullen P, Allaire N, Scannevin RH. Dimethyl fumarate alters microglia phenotype and protects neurons against proinflammatory toxic microenvironments. J Neuroimmunol. 2016 Oct 15;299:35-44. doi: 10.1016/j.jneuroim.2016.08.006. Epub 2016 Aug 5. PubMed PMID: 27725119.