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CAS No 28380-24-7 , Nigericin

  • Name: Nigericin
  • Synonyms: Antibiotic K 178; Antibiotic X 464; Stereoisomer oftetrahydro-6-[[9-methoxy-2,4,10-trimethyl-2-[octahydro-2,3'-dimethyl-5'-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-a,3-dimethyl-2H-pyran-2-aceticacid; X 464;Azalomycin M; Antibiotic M 2;1,6-Dioxaspiro[4.5]decane,nigericin deriv.; Helixin C; Polyetherin A;Nigericin;
  • CAS Registry Number:
  • Transport: UN 3462 6
  • Melting Point: 245-255ºC
  • Flash Point: 226.9°C
  • Boiling Point: 779.9°Cat760mmHg
  • Density: 1.19g/cm3
  • Refractive index: 1.543
  • Water Solubility: Soluble in DMSO (50 mg/mL) and ethanol (20 mg/mL)
  • Safety Statements: 26-36/37/39-45
  • Hazard Symbols: T: Toxic;
  • Flash Point: 226.9°C
  • Molecular Weight: 746.94
  • InchiKey: DANUORFCFTYTSZ-SJSJOXFOSA-N
  • InChI: InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
  • Risk Statements: 25-36/37/38
  • Molecular Formula: C40H67NaO11
  • Molecular Structure:CAS No:28380-24-7 Nigericin

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28380-24-7 NIGERICIN

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28380-24-7 Nigericin

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References of Nigericin
Title: Nigericin
CAS Registry Number: 28380-24-7
Synonyms: Antibiotic K 178; antibiotic X-464; azalomycin M; helixin C; polyetherin A
Molecular Formula: C40H68O11
Molecular Weight: 724.96
Percent Composition: C 66.27%, H 9.45%, O 24.28%
Literature References: Polyether antibiotic which affects ion transport and ATPase activity in mitochondria; produced by Streptomyces hygroscopicus E-749 and structurally related to monensin, q.v. Isoln, characterization, production: R. L. Harned et al., Antibiot. Chemother. 1, 594 (1951); J. Berger et al., J. Am. Chem. Soc. 73, 5295 (1951); J. Shoji et al., J. Antibiot. 21, 402 (1968). Structure: L. K. Steinrauf et al., Biochem. Biophys. Res. Commun. 33, 29 (1968); T. Kubota et al., Chem. Commun. 1968, 1541; T. Kubota, S. Matsutani, J. Chem. Soc. C 1970, 695. Use in coccidiosis: M. Gorman, R. L. Hamill, US 3555150 (1971 to Lilly). Effect on calcium uptake and membrane potential in mitochondria: H. Rottenberg, A. Scarpa, Biochemistry 13, 4811 (1974). Stimulation of ATPase activity: H. Sze, Proc. Natl. Acad. Sci. USA 77, 5904 (1980). Approach to synthesis: C. P. Holmes, P. A. Bartlett, J. Org. Chem. 54, 98 (1989).
Properties: Colorless needles, mp 183.5-185°. [a]D24 +36.2° (c = 0.842 in CHCl3). Sol in alcohols, acetone, ethyl acetate, chloroform, benzene, ether; slightly sol in satd hydrocarbons. Practically insol in water. LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned).
Melting point: mp 183.5-185°
Optical Rotation: [a]D24 +36.2° (c = 0.842 in CHCl3)
Toxicity data: LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned)
 
Derivative Type: Sodium salt
Molecular Formula: C40H67NaO11
Molecular Weight: 746.94
Percent Composition: C 64.32%, H 9.04%, Na 3.08%, O 23.56%
Properties: Crystals, mp 245-255° (dec). Sol in chloroform. Practically insol in water.
Melting point: mp 245-255° (dec)