Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H2O4 |
| Molecular Weight | 114.0563 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C(=O)C1=O
InChI
InChIKey=PWEBUXCTKOWPCW-UHFFFAOYSA-N
InChI=1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
Squaric acid is a dibasic organic acid and useful intermediate in a variety of synthetic reactions involving the synthesis of photosensitive squarylium dyes and inhibitors of protein tyrosine phosphatases. Medically, squaric acid dibutyl ester or dibutyl squarate derives from a squaric acid is used for the treatment of warts.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Squaric acid-based peptidic inhibitors of matrix metalloprotease-1. | 2005 Dec 23 |
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| A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety. | 2005 Nov |
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| Reductive cyclotetramerization of CO to squarate by a U(III) complex: the X-ray crystal structure of [(U (eta-C8H6{SiiPr3-1,4}2)(eta-C5Me4H)]2(mu-eta2: eta2-C4O4). | 2006 Aug 2 |
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| Structural and spectroscopic analysis of hydrogensquarates of glycine-containing tripeptides. | 2006 Dec 5 |
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| VF(C4O4)(H2O)2: a new layer type of diaquavanadium(III) fluoride squarate. | 2006 Jan |
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| The design of organic catalysis for epoxidation by hydrogen peroxide. | 2006 Jul |
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| Structural diversity in manganese squarate frameworks using N,N-donor chelating/bridging ligands: syntheses, crystal structures and magnetic properties. | 2006 Mar 28 |
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| A new series of glycopeptide antibiotics incorporating a squaric acid moiety. Synthesis, structural and antibacterial studies. | 2006 Sep |
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| Exploring alternative Zn-binding groups in the design of HDAC inhibitors: squaric acid, N-hydroxyurea, and oxazoline analogues of SAHA. | 2006 Sep 15 |
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| Molecular structure, infrared spectrum, and photochemistry of squaric acid dimethyl ester in solid argon. | 2006 Sep 28 |
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| Functionalization of oligosaccharide mimetics and multimerization using squaric diester-mediated coupling. | 2007 Apr 9 |
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| Preparation of carbohydrate-oligonucleotide conjugates using the squarate spacer. | 2007 Dec 1 |
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| Dual-mode semisquaraine-based sensor for selective detection of Hg2+ in a micellar medium. | 2007 Jan 4 |
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| [Synthesis of oligosaccharide fragments of mannan from Candida albicans cell wall and their BSA conjugates]. | 2007 Jan-Feb |
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| Synthesis and characterization of covalent mimics of phosphatidylinositol-4,5-bisphosphate micelles. | 2007 Jun |
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| Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium. | 2007 Jun 15 |
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| Complexes of aminosquarate ligands with first-row transition metals and lanthanides: new insights into their hydrolysis. | 2007 Jun 25 |
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| Spectroscopic, theoretical and structural characterization of hydrogensquarates of L-threonyl-L-serine and L-serine. | 2007 Nov |
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| Biphenyls as potent vitronectin receptor antagonists. Part 3: Squaric acid amides. | 2007 Nov 15 |
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| Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides. | 2007 Nov 8 |
|
| Structural and spectroscopic elucidation of tetrapetide glycyl-(L)-prolyl-glycyl-glycine and its hydrogensquarate. | 2008 |
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| Synthesis, growth and characterization of a new nonlinear optical material: 4-phenylpyridinium hydrogen squarate (4PHS). | 2008 Apr |
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| Carbonyl groups as molecular valves to regulate chloride binding to squaramides. | 2008 Aug 7 |
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| Preparation of glycoconjugates by dialkyl squarate chemistry revisited. | 2008 Feb 4 |
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| Very large difference in electronic communication of dimetal species with heterobiphenylene and heteroanthracene units. | 2008 Jan 7 |
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| Structural effects on interconversion of oxygen-substituted bisketenes and cyclobutenediones. | 2008 Mar 7 |
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| Successful treatment of recalcitrant warts with topical squaric acid in immunosuppressed child. | 2008 Mar-Apr |
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| Alkylsquarates as key intermediates for the rapid preparation of original drug-inspired compounds. | 2008 May |
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| Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate. | 2008 Nov 15 |
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| Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. | 2008 Nov 5 |
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| Synthesis of a 200-member library of squaric acid N-hydroxylamide amides. | 2008 Sep 15 |
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| A monoclinic pseudopolymorph of manganese squarate dihydrate, Mn(mu-C(4)O(4))(H(2)O)(2), built from cubic units. | 2009 Apr |
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| Crystal structures and spectroscopic properties of ester amide and diamide of squaric acid with prolinamide. | 2009 Apr |
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| Self-assembly of hydrogensquarates: crystal structures and properties. | 2009 Apr 2 |
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| Synthesis, conjugation, and immunological evaluation of the serogroup 6 pneumococcal oligosaccharides. | 2009 Dec 14 |
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| Squaramide hydroxamate-based chemidosimeter responding to iron(III) with a fluorescence intensity increase. | 2009 Feb 2 |
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| Synthesis of a heptasaccharide fragment of the mannan from Candida guilliermondii cell wall and its conjugate with BSA. | 2009 Jan 5 |
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| Reductive disproportionation of carbon dioxide to carbonate and squarate products using a mixed-sandwich U(III) complex. | 2009 Jan 8 |
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| Synthesis of novel organic-inorganic hybrid compounds: lanthanide phosphites incorporating a squarate ligand. | 2009 Jul 20 |
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| Temperature- and pressure-induced proton transfer in the 1:1 adduct formed between squaric acid and 4,4'-bipyridine. | 2009 Mar 25 |
|
| Identification and SAR of squarate inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2). | 2009 May 1 |
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| A new scandium metal organic framework built up from octadecasil zeolitic cages as heterogeneous catalyst. | 2009 May 7 |
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| A light-emitting mouse to image skin inflammation. | 2009 May-Jun |
|
| Rare earth metal squarates incorporating ethylene glycol ligand with a three-dimensional framework structure: RE(C(4)O(4))(1.5)(C(2)H(6)O(2)) (RE = Y, La-Nd, Sm-Lu). | 2009 Nov 28 |
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| L-Leucinamide hydrogensquarate: spectroscopic and structural elucidation. | 2009 Oct |
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| 1,10-Phenanthrolinium hydrogensquarate monohydrate--a non-centrosymmetric structure from two non-chiral agents. | 2009 Sep 1 |
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| Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant. | 2010 Jan |
|
| Calculations of the relative energies of the 2B1g and 2A2u states of cyclobutanetetraone radical cation and radical anion provide further evidence of a 3B2u ground state for the neutral molecule: a proposed experimental test of the prediction of a triplet ground state for (CO)4. | 2010 Jan 28 |
|
| Synthesis of 3,6-branched oligomannoside fragments of the mannan from Candida albicans cell wall corresponding to the antigenic factor 4. | 2010 Jul 2 |
|
| 2-(Phenylethyl)ammonium hydrogensquarate hemihydrate: crystal structure, solid-state IR-spectroscopic and theoretical characterization. | 2010 Jun |
Patents
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SUB15362MIG
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220-761-4
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m10167
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SQUARIC ACID
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SUBSTANCE RECORD
