Home > Name List By 7 > 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)- China

CAS No 121-40-4 , 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)- Search by region : China

  • Name: 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)-
  • Synonyms: 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, stereoisomer (8CI);7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R)-; (-)-Terreic acid;7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)-; Terreic acid (6CI);
  • CAS Registry Number:
  • Density: 1.613 g/cm3
  • Refractive index: 1.618
  • Water Solubility: Soluble in water (3 mg/mL with warming and stirring)
  • Molecular Weight: 154.12
  • InChI: InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
  • Molecular Formula: C7H6O4
  • Molecular Structure:CAS No:121-40-4 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)-

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121-40-4 (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE

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121-40-4 (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO4.1.0HEPT-3-ENE-2,5-DIONE

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References of 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-, (1R,6S)-
Title: Terreic Acid
CAS Registry Number: 121-40-4
CAS Name: (1R)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Synonyms: 2-hydroxy-3-methyl-1,4-benzoquinone 5,6-epoxide; 5,6-epoxy-3-hydroxy-p-toluquinone
Molecular Formula: C7H6O4
Molecular Weight: 154.12
Percent Composition: C 54.55%, H 3.92%, O 41.52%
Literature References: Antibiotic metabolite produced by the mold Aspergillus terreus; naturally occurring as the (-)-form: Wilkins, Harris, Br. J. Exp. Pathol. 23, 166 (1942); Abraham, Florey, in H. W. Florey et al., Antibiotics vol. I (Oxford Univ. Press, New York, 1949) p 337; Kaplan et al., Antibiot. Chemother. 4, 746 (1954). Structure: Sheehan et al., J. Am. Chem. Soc. 80, 5536 (1958). Synthesis of the racemate: Rashid, Read, J. Chem. Soc. C 1967, 1323. Alternate synthesis and resolution of isomers: Sheehan, Lo, J. Med. Chem. 17, 371 (1974). Improved synthesis: A. Enhsen et al., J. Org. Chem. 55, 1177 (1990).
Properties: Pale yellow plates from benzene or hexane. Easily sublimed in vacuo. mp 127-127.5°. Rotation varies considerably with the solvent: [a]D22 -16.6° (chloroform); [a]D22 -28.6° (methanol-benzene 1:1); [a]D22 +74.3° (pH 7 phosphate buffer). uv max (ethanol): 214, 316 nm (log e 4.03, 3.88). Enol-type acid, pKa 4.5. Slightly sol in water. Soluble in ether, lower alcohols, acetone, hot cyclohexane. Moderately stable to mineral acid, but dec rapidly in alkaline soln.
Melting point: mp 127-127.5°
pKa: pKa 4.5
Optical Rotation: [a]D22 -16.6° (chloroform); [a]D22 -28.6° (methanol-benzene 1:1); [a]D22 +74.3° (pH 7 phosphate buffer)
Absorption maximum: uv max (ethanol): 214, 316 nm (log e 4.03, 3.88)