4971-56-6,MFCD00010086
Catalog No.:AA003UOT

4971-56-6 | Tetronic acid

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250mg
98%
in stock  
$9.00   $7.00
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1g
98%
in stock  
$29.00   $21.00
- +
5g
96%
in stock  
$107.00   $75.00
- +
25g
96%
in stock  
$474.00   $332.00
- +
100g
96%
in stock  
$1,808.00 $1,266.00
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA003UOT
Chemical Name:
Tetronic acid
CAS Number:
4971-56-6
Molecular Formula:
C4H4O3
Molecular Weight:
100.0728
MDL Number:
MFCD00010086
SMILES:
O=C1OCC(=O)C1
Properties
Properties
 
BP:
324.3°C at 760 mmHg  
Form:
Solid  
MP:
139-140 °C (dec.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
116  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
7  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
0  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-0.1  

Downstream Synthesis Route

[1]Heterocycles,1992,vol.33,p.67-72

[2]Heterocycles,1992,vol.33,p.67-72

[1]JournalofOrganicChemistry,1983,vol.48,p.1914-1916

4971-56-6    39996-22-0   
2-hydroxymethyl-6,7-dimethoxy-4-phenylquinoline-3-carboxylicacidlactone 

[1]ChemicalandPharmaceuticalBulletin,1999,vol.47,p.369-374

[1]RussianJournalofOrganicChemistry,2003,vol.39,p.998-1009

[1]JournalofOrganicChemistry,2004,vol.69,p.3943-3949

Literature

Title: Quartromicin biosynthesis: two alternative polyketide chains produced by one polyketide synthase assembly line.

Journal: Chemistry & biology 20121026

Title: Isolation, antimicrobial activity, and absolute configuration of the furylidene tetronic acid core of pestalotic acids A-G.

Journal: Organic & biomolecular chemistry 20120721

Title: A novel vitamin K1 2,3-epoxide reductase (VKOR) inhibitor, 3-acetyl-5-methyltetronic acid, reduces experimental glomerulonephritis.

Journal: The Journal of veterinary medical science 20120701

Title: Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety.

Journal: Journal of agricultural and food chemistry 20111214

Title: A photocycloaddition/fragmentation approach toward the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane skeleton of terpenoid natural products.

Journal: Organic letters 20110401

Title: Convergent route to the spirohexenolide macrocycle.

Journal: Organic letters 20101015

Title: Total synthesis of punctaporonin C by a regio- and stereoselective [2+2]-photocycloaddition.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20100525

Title: In vitro reconstruction of tetronate RK-682 biosynthesis.

Journal: Nature chemical biology 20100201

Title: Tetramic and tetronic acids as scaffolds in bioinorganic and bioorganic chemistry.

Journal: Bioinorganic chemistry and applications 20100101

Title: Stereoselective synthesis of (E)-2-en-4-ynoic acids with ynolates: catalytic conversion to tetronic acids and 2-pyrones.

Journal: Organic letters 20091203

Title: Asymmetric synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-beta-lactones including facile conversion to tetronic acids: application to (+)-maculalactone A.

Journal: The Journal of organic chemistry 20090703

Title: 3-Aryltetronic acids: efficient preparation and use as precursors for vulpinic acids.

Journal: The Journal of organic chemistry 20090206

Title: Synthesis of pulvinic derivatives via TBAF-mediated regioselective opening of an unsymmetrical monoaromatic pulvinic dilactone.

Journal: The Journal of organic chemistry 20081205

Title: Cytotoxic and antiplasmodial substances from marine-derived fungi, Nodulisporium sp. and CRI247-01.

Journal: Phytochemistry 20081001

Title: A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides.

Journal: Bioorganic & medicinal chemistry letters 20080715

Title: Analysis of the tetronomycin gene cluster: insights into the biosynthesis of a polyether tetronate antibiotic.

Journal: Chembiochem : a European journal of chemical biology 20080505

Title: Tetramic and tetronic acids: an update on new derivatives and biological aspects.

Journal: Bioorganic & medicinal chemistry 20080415

Title: Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): tetramic, tetronic acids and dihydropyridin-2-ones.

Journal: Bioorganic & medicinal chemistry letters 20080315

Title: An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives and related compounds under ultrasound irradiation without catalyst.

Journal: Ultrasonics sonochemistry 20080301

Title: Glyceryl-S-acyl carrier protein as an intermediate in the biosynthesis of tetronate antibiotics.

Journal: Chembiochem : a European journal of chemical biology 20080104

Title: Coordination behavior of 3-ethoxycarbonyltetronic acid towards Cu(II) and Co(II) metal ions.

Journal: Bioinorganic chemistry and applications 20080101

Title: A concise organocatalytic and enantioselective synthesis of isotetronic acids.

Journal: Chemical communications (Cambridge, England) 20071207

Title: Naphthyl tetronic acids as multi-target inhibitors of bacterial peptidoglycan biosynthesis.

Journal: ChemMedChem 20071001

Title: Domino syntheses of bioactive tetronic and tetramic acids.

Journal: Die Naturwissenschaften 20070101

Title: Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

Journal: Organic letters 20060511

Title: Synthesis of tetramic and tetronic acids as beta-secretase inhibitors.

Journal: Journal of combinatorial chemistry 20060101

Title: Conformationally constrained beta-amino acid derivatives by intramolecular [2 + 2]-photocycloaddition of a tetronic acid amide and subsequent lactone ring opening.

Journal: The Journal of organic chemistry 20051125

Title: Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins.

Journal: The Journal of organic chemistry 20050722

Title: Synthesis of the fully functionalized core structure of the antibiotic abyssomicin C.

Journal: Organic letters 20050707

Title: Enantioselective syntheses and configuration assignments of gamma-chiral butenolides from Plagiomnium undulatum: butenolide synthesis from tetronic acids.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20050318

Title: Lipopolysaccharides of Vibrio cholerae II. Genetics of biosynthesis.

Journal: Biochimica et biophysica acta 20041014

Title: Non-peptidic HIV protease inhibitors.

Journal: Current topics in medicinal chemistry 20040101

Title: [Bis(lactone)-annulated 4H-pyranes and 1,4-dihydropyridines from 3,3'-(nitrobenzlidene)-bistetronic acids].

Journal: Die Pharmazie 20020901

Title: Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and cdc25B inhibition.

Journal: Journal of medicinal chemistry 20010927

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SDS
Related Products of 4971-56-6
Tags:4971-56-6 Molecular Formula|4971-56-6 MDL|4971-56-6 SMILES|4971-56-6 Tetronic acid
Catalog No.: AA003UOT
4971-56-6,MFCD00010086
4971-56-6 | Tetronic acid
Pack Size: 250mg
Purity: 98%
in stock
$9.00 $7.00
Pack Size: 1g
Purity: 98%
in stock
$29.00 $21.00
Pack Size: 5g
Purity: 96%
in stock
$107.00 $75.00
Pack Size: 25g
Purity: 96%
in stock
$474.00 $332.00
Pack Size: 100g
Purity: 96%
in stock
$1,808.00 $1,266.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA003UOT
Chemical Name: Tetronic acid
CAS Number: 4971-56-6
Molecular Formula: C4H4O3
Molecular Weight: 100.0728
MDL Number: MFCD00010086
SMILES: O=C1OCC(=O)C1
Properties
BP: 324.3°C at 760 mmHg  
Form: Solid  
MP: 139-140 °C (dec.)  
Storage: Inert atmosphere;2-8℃;  
Complexity: 116  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 7  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 0  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -0.1  
Downstream Synthesis Route
4971-56-6    1123-86-0    107-30-2    141548-68-7    141548-68-7 

[1]Heterocycles,1992,vol.33,p.67-72

[2]Heterocycles,1992,vol.33,p.67-72

4971-56-6    16357-83-8    85422-48-6 

[1]JournalofOrganicChemistry,1983,vol.48,p.1914-1916

4971-56-6    39996-22-0   
2-hydroxymethyl-6,7-dimethoxy-4-phenylquinoline-3-carboxylicacidlactone 

[1]ChemicalandPharmaceuticalBulletin,1999,vol.47,p.369-374

4971-56-6    20291-40-1    375374-83-7 

[1]RussianJournalofOrganicChemistry,2003,vol.39,p.998-1009

4971-56-6    456-64-4    157123-01-8 

[1]JournalofOrganicChemistry,2004,vol.69,p.3943-3949

Literature fold

Title: Quartromicin biosynthesis: two alternative polyketide chains produced by one polyketide synthase assembly line.

Journal: Chemistry & biology20121026

Title: Isolation, antimicrobial activity, and absolute configuration of the furylidene tetronic acid core of pestalotic acids A-G.

Journal: Organic & biomolecular chemistry20120721

Title: A novel vitamin K1 2,3-epoxide reductase (VKOR) inhibitor, 3-acetyl-5-methyltetronic acid, reduces experimental glomerulonephritis.

Journal: The Journal of veterinary medical science20120701

Title: Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety.

Journal: Journal of agricultural and food chemistry20111214

Title: A photocycloaddition/fragmentation approach toward the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane skeleton of terpenoid natural products.

Journal: Organic letters20110401

Title: Convergent route to the spirohexenolide macrocycle.

Journal: Organic letters20101015

Title: Total synthesis of punctaporonin C by a regio- and stereoselective [2+2]-photocycloaddition.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20100525

Title: In vitro reconstruction of tetronate RK-682 biosynthesis.

Journal: Nature chemical biology20100201

Title: Tetramic and tetronic acids as scaffolds in bioinorganic and bioorganic chemistry.

Journal: Bioinorganic chemistry and applications20100101

Title: Stereoselective synthesis of (E)-2-en-4-ynoic acids with ynolates: catalytic conversion to tetronic acids and 2-pyrones.

Journal: Organic letters20091203

Title: Asymmetric synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-beta-lactones including facile conversion to tetronic acids: application to (+)-maculalactone A.

Journal: The Journal of organic chemistry20090703

Title: 3-Aryltetronic acids: efficient preparation and use as precursors for vulpinic acids.

Journal: The Journal of organic chemistry20090206

Title: Synthesis of pulvinic derivatives via TBAF-mediated regioselective opening of an unsymmetrical monoaromatic pulvinic dilactone.

Journal: The Journal of organic chemistry20081205

Title: Cytotoxic and antiplasmodial substances from marine-derived fungi, Nodulisporium sp. and CRI247-01.

Journal: Phytochemistry20081001

Title: A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides.

Journal: Bioorganic & medicinal chemistry letters20080715

Title: Analysis of the tetronomycin gene cluster: insights into the biosynthesis of a polyether tetronate antibiotic.

Journal: Chembiochem : a European journal of chemical biology20080505

Title: Tetramic and tetronic acids: an update on new derivatives and biological aspects.

Journal: Bioorganic & medicinal chemistry20080415

Title: Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): tetramic, tetronic acids and dihydropyridin-2-ones.

Journal: Bioorganic & medicinal chemistry letters20080315

Title: An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives and related compounds under ultrasound irradiation without catalyst.

Journal: Ultrasonics sonochemistry20080301

Title: Glyceryl-S-acyl carrier protein as an intermediate in the biosynthesis of tetronate antibiotics.

Journal: Chembiochem : a European journal of chemical biology20080104

Title: Coordination behavior of 3-ethoxycarbonyltetronic acid towards Cu(II) and Co(II) metal ions.

Journal: Bioinorganic chemistry and applications20080101

Title: A concise organocatalytic and enantioselective synthesis of isotetronic acids.

Journal: Chemical communications (Cambridge, England)20071207

Title: Naphthyl tetronic acids as multi-target inhibitors of bacterial peptidoglycan biosynthesis.

Journal: ChemMedChem20071001

Title: Domino syntheses of bioactive tetronic and tetramic acids.

Journal: Die Naturwissenschaften20070101

Title: Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

Journal: Organic letters20060511

Title: Synthesis of tetramic and tetronic acids as beta-secretase inhibitors.

Journal: Journal of combinatorial chemistry20060101

Title: Conformationally constrained beta-amino acid derivatives by intramolecular [2 + 2]-photocycloaddition of a tetronic acid amide and subsequent lactone ring opening.

Journal: The Journal of organic chemistry20051125

Title: Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins.

Journal: The Journal of organic chemistry20050722

Title: Synthesis of the fully functionalized core structure of the antibiotic abyssomicin C.

Journal: Organic letters20050707

Title: Enantioselective syntheses and configuration assignments of gamma-chiral butenolides from Plagiomnium undulatum: butenolide synthesis from tetronic acids.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20050318

Title: Lipopolysaccharides of Vibrio cholerae II. Genetics of biosynthesis.

Journal: Biochimica et biophysica acta20041014

Title: Non-peptidic HIV protease inhibitors.

Journal: Current topics in medicinal chemistry20040101

Title: [Bis(lactone)-annulated 4H-pyranes and 1,4-dihydropyridines from 3,3'-(nitrobenzlidene)-bistetronic acids].

Journal: Die Pharmazie20020901

Title: Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and cdc25B inhibition.

Journal: Journal of medicinal chemistry20010927

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