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Steroid


DATA No : SST0004 INFORMANT : Hideaki Nishino

NAME : 5a-Spirostan-3b,6a-diol

COMMON NAME: Chlorogenin
SYMBOL:
FORMULA: C27H44O4 MOL.WT (average) : 432.636


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BIOLOGICAL ACTIVITY
Saponin useful as fish poisons. (Ref. 0025)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:273-276degC, 154-155degC (diacetate) (Ref. 0023)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]24/546 = -52deg (chloroform or isopropanol) (Ref. 0023)

DENSITY:

SOLUBILITY:Sol in methanol, isopropanol. (Ref. 0023)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:d (pyridine) 0.83 (19-Me), 0.86 (18-Me), 1.12d(21-Me, J=7Hz), 1.05d (27-Me, J=7Hz), 3.30d (26-H2, J=11Hz), 3.39dd (26-H2, J=11, 3Hz), 4.45ddd (16-H, J=7, 7, 7Hz), 3.70m (3H and 6H). (Ref. 0024)

MASS SPECTRA:m/e 432 (Ref. 0024)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Root of amole (California soap plant, lily family, Chlorogalum pomeridianum Kunth) (Ref. 0025)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. (Ref. 0019) Conversion to tigogenin. (Ref. 0023)
REFERENCES
[0019]
AUTHOR:Marker,R.E., and Rohrmann,E.
TITLE:Sterols. LVIII. The Position of the Nuclear Hydroxyl Groups in Chlorogenin.
JOURNAL:J.Am.Chem.Soc.
VOL:61 PAGE : 946 -949 (1939)
[TOP]

[0023]
AUTHOR:Marker,R.E., Turner,D.L., and Ulshafer,P.R.
TITLE:Sterols. CXI. Sapogenins. XL. The Conversion of Chlorogenin to Tigogenin.
JOURNAL:J.Am.Chem.Soc.
VOL:62 PAGE : 3009 -3010 (1940)
[TOP]

[0024]
AUTHOR:Chakravarty,A.K., Dhar,T.K., and Pakrashi,S.C.
TITLE:Hispigenin, a Novel 22bo-Spirostane from Solanum Hispidum
JOURNAL:Tetrahedron Lett.
VOL:1978 PAGE : 3875 -3878 (1978)
[TOP]

[0025]
AUTHOR:Liang,P., and Noller,C.R.
TITLE:Saponins and Sapogenins. III. The Sapogenins Obtained from Chlorogalum Pomeridianum
JOURNAL:J.Am.Chem.Soc.
VOL:57 PAGE : 525 -527 (1935)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.