Stigmasterol

SKU: S0267

Category: Steroids

Synonyms: 3β-Hydroxy-24-ethyl-5,22-cholestadiene , 5,22-Stigmastadien-3β-ol , Stigmasterin , Phytosterol , β-Stigmasterol , Serposterol , Wulzen anti-stiffness Factor , NSC8095; 83-48-7
CAS-Number: C₂₉H₄₈O
Molecular Formula: 412.69
Molecular Weight

Product Data
Handling
Safety Information
Details

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)

Short Term Storage: +4°C
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Shipping: AMBIENT

Transportation: Not dangerous goods

Description: 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.
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
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 Key: HCXVJBMSMIARIN-PHZDYDNGSA-N
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

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.

SKU: S0267 Category: Steroids

Additional information

Additional information

Synonyms	3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin, Phytosterol, β-Stigmasterol, Serposterol, Wulzen anti-stiffness Factor, NSC8095
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