Stigmasterol

Specifications / Handling

More Information
Product Details
Synonyms	Stigmasterin; Phytosterol; β-Stigmasterol; Serposterol; Wulzen anti-stiffness Factor; NSC8095
Product Type	Chemical
Properties
Formula	C₂₉H₄₈O
MW	412.7
CAS	83-48-7
Source/Host Chemicals	Synthetic. Originally isolated from various plants and marine organisms.
Purity Chemicals	≥95% (NMR)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO, ethanol or dimethylformamide. Sparingly soluble in water.
Identity	Determined by ¹-H-NMR.
InChi Key	HCXVJBMSMIARIN-PHZDYDNGSA-N
Smiles	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Anti-hypercholestrolemic compound [1, 7].
Anti-inflammatory and immune-modulating effects [2, 4].
Anticancer compound. Chemopreventive [3, 12, 13].
Cytostatic. Cell growth inhibitor [5].
Antimutagenic [6].
Potent in vitro antagonist of FXR (farnesoid X receptor) [8].
DNA polymerase β inhibitor [9].
Potent antioxidant, hypoglycemic and thyroid inhibiting agent [10].
Anti-osteoarthritic. Decreases the expression of matrix metalloproteinases [11].
Neuroprotective [15].
Is used as a precursor for synthetic progesterone and vitamin D3 and is an intermediate in the biosynthesis of androgens, estrogens and corticoids [14].

Product References

Antihypercholesterolemic studies with sterols: beta-sitosterol and stigmasterol: R.F. Chandler, et al.; J. Pharm. Sci. 68, 245 (1979)
Topical antiinflammatory activity of phytosterols isolated from Eryngium foetidum on chronic and acute inflammation models: M.D. Garcia, et al.; Phytother. Res. 13, 78 (1999)
Phytosterols as anticancer dietary components: evidence and mechanism of action: A.B. Awad & C.S. Fink; J. Nutr. 130, 2127 (2000) (Review)
Anti-Inflammatory and Immunomodulating Properties of a Sterol Fraction from Sideritis foetens CLEM: N. Antonio, et al.; Biol. Pharm. Bull. 24, 470 (2001)
Cyostatic activity of Achillea ageratum L.: M.A. Gomez, et al.; Phytother. Res. 15, 633 (2001)
Antimutagenic Constituents from the Thorns of Gleditsia sinensis: L. Jae-Chul, et al.; Chem. Pharm. Bull. 53, 561 (2005)
Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat: A.K. Batta, et al.; Metabolism 55, 292 (2006)
Stigmasterol, a soy lipid-derived phytosterol, is an antagonist of the bile acid nuclear receptor FXR: B.A. Carter, et al.; Pediatr. Res. 62, 301 (2007)
Inhibitors of DNA polymerase β: Activity and mechanism: G. Zhijie, et al.; Bioorg. Med. Chem. 16, 4331 (2008)
Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma: S. Panda, et al.; Fitoterapia 80, 123 (2009)
Stigmasterol: a phytosterol with potential anti-osteoarthritic properties: O. Gabay, et al.; Osteoarthritis Cartilage 18, 106 (2010)
Cytotoxic and apoptotic effects of the oxidized derivatives of stigmasterol in the U937 human monocytic cell line: Y.C. O'Callaghan, et al.; J. Agric. Food Chem. 58, 10793 (2010)
Phytosterols: perspectives in human nutrition and clinical therapy: S.P. Choudhary & L.S. Tran; Curr. Med. Chem. 18, 4557 (2011) (Review)
Stigmasterol: A comprehensive review: N. Kaur, et al.; IJPSR 2, 2259 (2011) (Review)
Rhinacanthus nasutus Extracts Prevent Glutamate and Amyloid-β Neurotoxicity in HT-22 Mouse Hippocampal Cells: Possible Active Compounds Include Lupeol, Stigmasterol and β-Sitosterol: J.M. Brimson, et al.; Int. J. Mol. Sci. 13, 5074 (2012)

Call	+41 61 926 6040
Fax	+41 61 926 6049