Difference between revisions of "Sarsasapogenin"

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'''Sarsasapogenin''' is a [[steroid]].
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'''Sarsasapogenin''' is a [[steroid]]al [[sapogenin]], that is the aglycosidic portion of a plant [[saponin]]. It is named after [[sarsaparilla]] (''[[Smilax]]'' sp.), a family of climbing plants found in subtropical regions. It was one of the first sapogenins to be identified, and the first [[spirostan]] steroid to be identified as such. The identification of the spirostan structure, with its ketone spiro acetal functionality, was fundamental in the development of the [[Marker degradation]], which allowed the industrial production of [[progesterone]] and other [[sex hormone]]s from plant steroids.
  
 
==References==
 
==References==

Revision as of 11:38, 7 March 2010

Sarsasapogenin
Sarsasapogenin.png
IUPAC name (3β,5β,25S)-spirostan-3-ol
Identifiers
InChI InChI=1/C27H44O3/c1-16-7-12-27 (29-15-16)17(2)24-23(30-27)14- 22-20-6-5-18-13-19(28)8-10-25( 18,3)21(20)9-11-26(22,24)4/h16 -24,28H,5-15H2,1-4H3/t16-,17-, 18+,19-,20+,21-,22-,23-,24-,25 -,26-,27+/m0/s1
InChIKey GMBQZIIUCVWOCD-WWASVFFGBR
Standard InChI InChI=1S/C27H44O3/c1-16-7-12-2 7(29-15-16)17(2)24-23(30-27)14 -22-20-6-5-18-13-19(28)8-10-25 (18,3)21(20)9-11-26(22,24)4/h1 6-24,28H,5-15H2,1-4H3/t16-,17- ,18+,19-,20+,21-,22-,23-,24-,2 5-,26-,27+/m0/s1
Standard InChIKey GMBQZIIUCVWOCD-WWASVFFGSA-N
CAS number [126-19-2]
EC number 204-776-3
ChemSpider 83145
Properties[1]
Chemical formula C27H44O3
Molar mass 416.64 g/mol
Melting point

199–199.5 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Sarsasapogenin is a steroidal sapogenin, that is the aglycosidic portion of a plant saponin. It is named after sarsaparilla (Smilax sp.), a family of climbing plants found in subtropical regions. It was one of the first sapogenins to be identified, and the first spirostan steroid to be identified as such. The identification of the spirostan structure, with its ketone spiro acetal functionality, was fundamental in the development of the Marker degradation, which allowed the industrial production of progesterone and other sex hormones from plant steroids.

References

  1. Jacobs, Walter A.; Simpson, James C. E. On Sarsasapogenin and Gitogenin. J. Biol. Chem. 1934, 105 (3), 501–10, <http://www.jbc.org/content/105/3/501.full.pdf>.

External links

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