Pavoninins
Title: Pavoninins
Literature References: Shark repellent compounds isolated from the defense secretion of the Pacific sole, Pardachirus pavoninus. Series of ichthyotoxic and hemolytic steroid amine glycosides; pavoninin-5 is the most abundant. Isoln, structure determn and evaluation of pavoninins 1-6 as shark repellents: K. Tachibana et al., Science 226, 703 (1984); and 13C- and 1H-NMR studies: eidem, Tetrahedron 41, 1027 (1985). Synthesis of pavoninin-1: Y. Ohnishi, K. Tachibana, Bioorg. Med. Chem. 5, 2251 (1997); of pavoninin-4: J. R. Williams et al., J. Org. Chem. 70, 10732 (2005).
 
Derivative Type: Pavoninin-1
CAS Registry Number: 94426-01-4
CAS Name: (7a,25R)-7-[[2-(Acetylamino)-2-deoxy-b-D-glucopyranosyl]oxy]-26-(acetyloxy)cholest-4-en-3-one
Molecular Formula: C37H59NO9
Molecular Weight: 661.87
Percent Composition: C 67.14%, H 8.98%, N 2.12%, O 21.76%
Properties: [a]D20 +19° (c = 1.1 in chloroform). uv max (methanol): 244 nm (Log e 4.1)
Optical Rotation: [a]D20 +19° (c = 1.1 in chloroform)
Absorption maximum: uv max (methanol): 244 nm (Log e 4.1)
 
Derivative Type: Pavoninin-4
CAS Registry Number: 94359-66-7
CAS Name: (3a,5a,15a,25R)-26-(Acetyloxy)-3-hydroxycholestan-15-yl 2-(acetylamino)-2-deoxy-b-D-glucopyranoside
Molecular Formula: C37H63NO9
Molecular Weight: 665.90
Percent Composition: C 66.74%, H 9.54%, N 2.10%, O 21.62%
Properties: White solid, mp 134-136°. [a]D20 +28° (c = 0.4 in ethanol).
Melting point: mp 134-136°
Optical Rotation: [a]D20 +28° (c = 0.4 in ethanol)
 
Derivative Type: Pavoninin-5
CAS Registry Number: 94480-49-6
CAS Name: (3b,15a,25R)-26-(Acetyloxy)-3-hydroxycholest-5-en-15-yl 2-(acetylamino)-2-deoxy-b-D-glucopyranoside
Molecular Formula: C37H61NO9
Molecular Weight: 663.88
Percent Composition: C 66.94%, H 9.26%, N 2.11%, O 21.69%
Properties: Sol in ethyl acetate. [a]D29 +21° (c = 0.7 in ethanol).
Optical Rotation: [a]D29 +21° (c = 0.7 in ethanol)

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