Specifications
- Purity
- ≥95% (HPLC)
- Identity
- 1H-NMR
- Appearance
- White to off-white powder
Properties
- Melting Point
- 165-167 °C (lit.)
- Solvents
- ethanol (20 mg/ml), DMF (1 mg/ml), chloroform (50 mg/ml)
Category: Steroids
Stigmasterol is a phytosterol with chemical structure similar to cholesterol and anti-hypercholestrolemic activity. It exhibits anticancer, anti-inflammatory, antioxidant, antidiabetic, neuroprotective and immune-modulating properties. Stigmasterol exhibits antitumor effects in cancer cells mediated via inhibition of cell migration, cell cycle arrest, apoptosis/autophagy induction and angiogenesis inhibition. Stigmasterol is a potent in vitro antagonist of FXR (farnesoid X receptor), a DNA polymerase β inhibitor and targets the GLUT4 glucose transporter. It has anti-osteoarthritic effects, by decreasing the expression of matrix metalloproteinases. Stigmasterol shows acetylcholinesterase inhibitory activity and also enriched glutamatergic synapses in cultures of brain neurons. It also has been shown to have antitrypanasomal and insecticidal activity and has been used as an adjuvant for beta lactam antibiotics against beta-lactamase positive clinical isolates. Stigmasterol is also used as a precursor for synthetic progesterone and vitamin D3 and is an intermediate in the biosynthesis of androgens, estrogens and corticoids.
Synonyms | 3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin, Phytosterol, β-Stigmasterol, Serposterol, Wulzen anti-stiffness Factor, NSC8095 |
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Purity | ≥95% (HPLC) |
Appearance | White to off-white powder |
CAS-Number | 83-48-7 |
Molecular Formula | C29H48O |
Molecular Weight | 412.69 |
Identity | 1H-NMR |
Solvents | ethanol (20 mg/ml), DMF (1 mg/ml), chloroform (50 mg/ml) |
Melting Point | 165-167 °C (lit.) |
Smiles | O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)/C=C/[C@@H](CC)C(C)C |
InChi Key | HCXVJBMSMIARIN-PHZDYDNGSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
Transportation | Not dangerous goods |
References | (1) R.F. Chandler, et al., J. Pharm. Sci. 68, 245 (1979), (2) A.B. Awad & C.S. Fink, J. Nutr. 130, 2127 (2000) (Review), (3) N. Antonio, et al., Biol. Pharm. Bull. 24, 470 (2001), (4) B.A. Carter, et al., Pediatr. Res. 62, 301 (2007), (5) G. Zhijie, et al., Bioorg. Med. Chem. 16, 4331 (2008), (6) O. Gabay, et al., Osteoarthritis Cartilage 18, 106 (2010), (7) Y.C. O'Callaghan, et al., J. Agric. Food Chem. 58, 10793 (2010), (8) S.P. Choudhary & L.S. Tran, Curr. Med. Chem. 18, 4557 (2011) (Review), (9) N. Kaur, et al., IJPSR 2, 2259 (2011) (Review), (10) J.M. Brimson, et al., Int. J. Mol. Sci. 13, 5074 (2012), (11) S. Gade, et al., Biochim. Biophys. Acta Gen. Subj. 1861, 541 (2017), (12) R. Aminu, et al., Biomed. Pharmacother. 89, 482 (2017), (13) C.I.B. Walker, et al., Naunyn Schmiedebergs Arch. Pharmacol. 390, 1163 (2017), (14) J. Wang, et al., Food Nutr. Res. 61, 1364117 (2017), (15) T.W. Yenn, et al., Steroids 128, 68 (2017), (16) T. Kangsamaksin, et al., PLoS One 12, e0189628 (2017), (17) M.N. Haque, et al., Nutr. Res. 56, 71 (2018), (18) K. Li, et al., J. BUON. 23, 1420 (2018), (19) S.I. Aboobucker & W.P. Suza, Front. Plant Sci. 10, 354 (2019) (Review), (20) J. Sun, et al., Neuropsychiatr. Dis. Treat. 15, 2991 (2019) |
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 |
Quantity | 5 g, 10 g, 25 g, Bulk |