Diosgenin

Diosgenin
Names


IUPAC name (3β,25R)-spirost-5-en-3-ol
Identifiers
CAS Number	512-04-9^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4629^N
ChEMBL	ChEMBL412437^Y
ChemSpider	89870^Y
ECHA InfoCard	100.007.396
EC Number	208-134-3
PubChem	99474
UNII	K49P2K8WLX^Y
InChI InChI=1S/C27H42O3/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/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1^Y Key: WQLVFSAGQJTQCK-VKROHFNGSA-N^Y InChI=1/C27H42O3/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/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1 Key: WQLVFSAGQJTQCK-VKROHFNGBS
SMILES O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)CC6)C
Properties
Chemical formula	C₂₇H₄₂O₃
Molar mass	414.63 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone), diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.

It is present in Costus speciosus, Smilax menispermoidea, species of Paris, Aletris, Trigonella, and Trillium, and many species of Dioscorea - D. althaeoides, colletti, futschauensis, gracillima, hispida, hypoglauca, floribunda, mexicana and composita nipponica, panthaica, parviflora, septemloba, and zingiberensis.

Diosgenin is a precursor for several hormones, starting with the Marker degradation process. This includes progesterone which in turn was used in early combined oral contraceptive pills. The unmodified steroid has estrogenic activity and can reduce the level of serum cholesterol.

Diosgenin may behave as a prodrug to progesterone.