Home > Name List By p > Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-

CAS No 24397-89-5 , Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-

  • Name: Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-
  • Synonyms: Isocoumarin,4-(2-aminopropionamido)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-(8CI); NSC 31083; Actinobolin; Propanamide,2-amino-N-(3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)-,[3R-[3a,4a(S*),4ab,5b,6a]]-; (+)-Actinobolin;Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-;
  • CAS Registry Number:
  • Flash Point: 311.9°C
  • Boiling Point: 592°Cat760mmHg
  • Density: 1.45g/cm3
  • Safety Statements: Poison by intravenous route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. An antimicrobial agent and experimental cariostat.
  • Flash Point: 311.9°C
  • Molecular Weight: 0
  • InChI: InChI=1S/C13H20N2O6/c1-4(14)12(19)15-10-5(2)21-13(20)8-6(16)3-7(17)11(18)9(8)10/h4-5,7,9-11,17-18,20H,3,14H2,1-2H3,(H,15,19)
  • Molecular Formula: C13H20 N2 O6
  • Molecular Structure:CAS No:24397-89-5 Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-

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24397-89-5 Actinobolin

  • Actinobolin, Min 99%
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24397-89-5 ACTINOBOLIN

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References of Propanamide,2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-
Title: Actinobolin
CAS Registry Number: 24397-89-5
CAS Name: (2S)-2-Amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]propanamide
Synonyms: 4-(2-aminopropionamido)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methylisocoumarin
Molecular Formula: C13H20N2O6
Molecular Weight: 300.31
Percent Composition: C 51.99%, H 6.71%, N 9.33%, O 31.97%
Literature References: Antibiotic produced by Streptomyces griseoviridus var atrofaciens; (+)-form is naturally occurring. Isoln and characterization: T. H. Haskell, Q. R. Bartz, Antibiot. Annu. 1958-1959, 505; T. H. Haskell et al., US 3043830 (1962 to Parke, Davis). Structural studies: Struck et al., Tetrahedron Lett. 1967, 1589; Munk et al., J. Am. Chem. Soc. 89, 4158 (1967). Structure: eidem, ibid. 90, 1087 (1968). Absolute configuration and chemistry: Antosz et al., ibid. 92, 4933 (1970). Crystal structure: J. B. Wetherington, J. W. Moncrief, Acta Crystallogr. B31, 501 (1975). Total synthesis: M. Yoshioka et al., J. Am. Chem. Soc. 106, 1133 (1984); eidem, Heterocycles 21, 151 (1984); R. S. Garigipati et al., J. Am. Chem. Soc. 107, 7790 (1985). Antibacterial activity and toxicity: R. F. Pittillo et al., Antibiot. Annu. 1958-1959, 497. Series of articles on antineoplastic activity: ibid. 515-532. Inhibition of protein synthesis: D. Smithers et al., Mol. Pharmacol. 5, 433 (1969). Experimental use as cariostat: D. E. Hunt et al., J. Dent. Res. 50, 371 (1971). Reduction of periodontal syndrome in mice, rats: J. H. Shaw, J. K. Ivimey, Arch. Oral Biol. 18, 357 (1973).
Properties: Amorphous, fluffy, very hygroscopic powder. [a]D28 +59° (c = 0.5 in pH 7 phosphate buffer). pKa: 7.5, 8.8. Freely sol in water; mod sol in methanol, ethanol. Unstable in aqueous solns pH >7. uv max: 262 nm (0.1N HCl); 288 nm (0.1N NaOH). LD50 in mice, rats (mg/kg): 800 ±27, 1550 ±26 i.v. (Pittillo).
pKa: pKa: 7.5, 8.8
Optical Rotation: [a]D28 +59° (c = 0.5 in pH 7 phosphate buffer)
Absorption maximum: uv max: 262 nm (0.1N HCl); 288 nm (0.1N NaOH)
Toxicity data: LD50 in mice, rats (mg/kg): 800 ±27, 1550 ±26 i.v. (Pittillo)
 
Derivative Type: Acetate
Molecular Formula: C13H20N2O6.C2H4O2
Molecular Weight: 360.36
Percent Composition: C 49.99%, H 6.71%, N 7.77%, O 35.52%
Properties: Needles from ethanol; softens at 130°, resolidifies at 145°, mp 263-266°. [a]D26 +58°. pKa: 4.6, 7.5, 8.8. Very sol in water; sol in warm methanol, ethanol, acetone; sparingly sol in ethyl acetate. uv max: 264 nm (pH 7 phosphate buffer).
Melting point: mp 263-266°
pKa: pKa: 4.6, 7.5, 8.8
Optical Rotation: [a]D26 +58°
Absorption maximum: uv max: 264 nm (pH 7 phosphate buffer)
 
Derivative Type: Hydrochloride
Molecular Formula: C13H20N2O6.HCl
Molecular Weight: 336.77
Percent Composition: C 46.36%, H 6.29%, N 8.32%, O 28.51%, Cl 10.53%
Properties: Hygroscopic. [a]D22 +59° (c = 0.41) (natural); [a]D22 +55° (c = 0.47) (synthetic).
Optical Rotation: [a]D22 +59° (c = 0.41) (natural); [a]D22 +55° (c = 0.47) (synthetic)