Stigmasterol

Stigmasterol

Names
IUPAC name (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names Stigmasterin; Wulzen anti-stiffness factor
Identifiers
CAS Number	83-48-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28824 N
ChEMBL	ChEMBL400247 Y
ChemSpider	4444352 Y
ECHA InfoCard	100.001.348
PubChem	5280794
UNII	99WUK5D0Y8 Y
InChI InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 Y Key: HCXVJBMSMIARIN-PHZDYDNGSA-N Y InChI=1/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 Key: HCXVJBMSMIARIN-PHZDYDNGBL
SMILES CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
Properties
Chemical formula	C29H48O
Molar mass	412.70 g·mol−1
Appearance	White solid
Melting point	160 to 164 °C (320 to 327 °F; 433 to 437 K)
Solubility in water	Insoluble
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

Stigmasterol (also known as Wulzen anti-stiffness factor) is a plant sterol, or phytosterol.

Wulzen factor, as it was first known, was discovered by University of California physiologist Rosalind Wulzen (born 1886).

Stigmasterol is an unsaturated phytosterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong), in Mirabilis jalapa and American Ginseng.

Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. Pasteurization will inactivate stigmasterol. Edible oils contains higher amount than vegetables. Phytosterols normally are broken down in the bile.

Stigmasterol is used as a precursor in the manufacture of semisynthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D₃.

The Upjohn company used stigmasterol as the starting raw material for the synthesis of cortisone.