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19466-47-8 | Stigmastan-3β-ol
CAS No: 19466-47-8 Catalog No: AG003UFI MDL No:
Product Description
Catalog Number:
AG003UFI
Chemical Name:
Stigmastan-3β-ol
CAS Number:
19466-47-8
Molecular Formula:
C29H52O
Molecular Weight:
416.7226
IUPAC Name:
(3S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChI:
InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI Key:
LGJMUZUPVCAVPU-KZXGMYDKSA-N
SMILES:
CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2[C@]1(C)CC[C@@H](C2)O)C
EC Number:
243-087-2
Properties
Complexity:
583
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
9
Defined Bond Stereocenter Count:
0
Exact Mass:
416.402g/mol
Formal Charge:
0
Heavy Atom Count:
30
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
416.734g/mol
Monoisotopic Mass:
416.402g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
20.2A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
10.2
Literature
| Title | Journal |
|---|---|
| Dietary plant stanols or sterols neither accumulate in stenotic aortic valves nor influence their structure or inflammatory status. | Clinical nutrition (Edinburgh, Scotland) 20151201 |
| Evaluation of the effect of plant sterols on the intestinal processing of cholesterol using an in vitro lipolysis model. | International journal of pharmaceutics 20121015 |
| Origin of fecal contamination in waters from contrasted areas: stanols as Microbial Source Tracking markers. | Water research 20120901 |
| Serum and lipoprotein sitostanol and non-cholesterol sterols after an acute dose of plant stanol ester on its long-term consumption. | European journal of nutrition 20120801 |
| Beneficial effects of sitostanol on the attenuated immune function in asthma patients: results of an in vitro approach. | PloS one 20120101 |
| Properties of β-sitostanol/DPPC monolayers studied with Grazing Incidence X-ray Diffraction (GIXD) and Brewster Angle Microscopy. | Journal of colloid and interface science 20111201 |
| Current therapy for patients with sitosterolemia--effect of ezetimibe on plant sterol metabolism. | Journal of atherosclerosis and thrombosis 20100930 |
| Exploratory characterization of the unsaponifiable fraction of tunisian virgin olive oils by a global approach with HPLC-APCI-IT MS/MS analysis. | Journal of agricultural and food chemistry 20100526 |
| TLR2 activation is essential to induce a Th1 shift in human peripheral blood mononuclear cells by plant stanols and plant sterols. | The Journal of biological chemistry 20100129 |
| Effect of rapeseed oil-derived plant sterol and stanol esters on atherosclerosis parameters in cholesterol-challenged heterozygous Watanabe heritable hyperlipidaemic rabbits. | The British journal of nutrition 20091201 |
| Chemometric approach to validating faecal sterols as source tracer for faecal contamination in water. | Water research 20091201 |
| [Comparison of the dietary phytosterols intake and serum lipids content in elderly women from three cities of China]. | Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20091201 |
| Lack of genoprotective effect of phytosterols and conjugated linoleic acids on Caco-2 cells. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090801 |
| Inhibition of intestinal absorption of cholesterol by surface-modified nanostructured aluminosilicate compounds. | Journal of pharmaceutical sciences 20090701 |
| Plant stanol ester spreads as components of a balanced diet for pregnant and breast-feeding women: evaluation of clinical safety. | The British journal of nutrition 20090601 |
| [Analysis of phytosterol contents in food plant materials and Chinese traditional medicines]. | Wei sheng yan jiu = Journal of hygiene research 20090301 |
| Dietary phytosterols and phytostanols alter the expression of sterol-regulatory genes in SHRSP and WKY inbred rats. | Annals of nutrition & metabolism 20090101 |
| Co-administration of berberine and plant stanols synergistically reduces plasma cholesterol in rats. | Atherosclerosis 20081101 |
| Effects of long-term plant sterol or stanol ester consumption on lipid and lipoprotein metabolism in subjects on statin treatment. | The British journal of nutrition 20081101 |
| [Studies on ethyl acetate soluble constituents of Huanglian Jiedutang]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901 |
| Study of thermodynamic parameters for solubilization of plant sterol and stanol in bile salt micelles. | Chemistry and physics of lipids 20080801 |
| Cholesterol absorption from the intestine is a major determinant of reverse cholesterol transport from peripheral tissue macrophages. | Arteriosclerosis, thrombosis, and vascular biology 20080701 |
| Modulation of cytokine production by plant sterols in stimulated human Jurkat T cells. | Molecular nutrition & food research 20080601 |
| Corn fiber oil and sitostanol decrease cholesterol absorption independently of intestinal sterol transporters in hamsters. | The Journal of nutritional biochemistry 20080401 |
| Moderately elevated plant sterol levels are associated with reduced cardiovascular risk--the LASA study. | Atherosclerosis 20080101 |
| Phospholipid transfer protein-deficient mice absorb less cholesterol. | Arteriosclerosis, thrombosis, and vascular biology 20070901 |
| [Analysis of phytosterol contents in Chinese plant food and primary estimation of its intake of people]. | Wei sheng yan jiu = Journal of hygiene research 20070501 |
| Detection of intermittent sewage pollution in a subtropical, oligotrophic, semi-enclosed embayment system using sterol signatures in sediments. | Environmental science & technology 20070201 |
| Determination of stigmasterol, beta-sitosterol and stigmastanol in oral dosage forms using high performance liquid chromatography with evaporative light scattering detection. | Journal of pharmaceutical and biomedical analysis 20060607 |
| Plant sterols and stanols: effects on mixed micellar composition and LXR (target gene) activation. | Journal of lipid research 20051101 |
| Quantitative determination of cholesterol, sitosterol, and sitostanol in cultured Caco-2 cells by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050725 |
| Ratio of lathosterol to campesterol in serum predicts the cholesterol-lowering effect of sitostanol-supplemented margarine. | International journal of clinical pharmacology and therapeutics 20050701 |
| Effects of sterol structure, temperature, and lipid medium on phytosterol oxidation. | Journal of agricultural and food chemistry 20041020 |
| Cholesterol absorption is mainly regulated by the jejunal and ileal ATP-binding cassette sterol efflux transporters Abcg5 and Abcg8 in mice. | Journal of lipid research 20040701 |
| Effect of phytosterols and phytostanols on the solubilization of cholesterol by dietary mixed micelles: an in vitro study. | Chemistry and physics of lipids 20040201 |
| Can cholesterol absorption be reduced by phytosterols and phytostanols via a cocrystallization mechanism? | Chemistry and physics of lipids 20040101 |
| Serum and aortic levels of phytosterols in rabbits fed sitosterol or sitostanol ester preparations. | Lipids 20031101 |
| Analysis of plant sterol and stanol esters in cholesterol-lowering spreads and beverages using high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectroscopy. | Journal of agricultural and food chemistry 20030910 |
| Measurement of intestinal cholesterol absorption by plasma and fecal dual-isotope ratio, mass balance, and lymph fistula methods in the mouse: an analysis of direct versus indirect methodologies. | Journal of lipid research 20030501 |
| Comparison of the intestinal uptake of cholesterol, plant sterols, and stanols in mice. | Journal of lipid research 20030301 |
| Non-nutritive bioactive constituents of plants: phytosterols. | International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20030301 |
| Comparison of the effects of sitostanol, sitostanol acetate, and sitostanol oleate on the inhibition of cholesterol absorption in normolipemic healthy male volunteers. A placebo controlled randomized cross-over study. | Arzneimittel-Forschung 20030101 |
| Consumption of tall oil-derived phytosterols in a chocolate matrix significantly decreases plasma total and low-density lipoprotein-cholesterol levels. | The British journal of nutrition 20021101 |
| Increased intestinal ABCA1 expression contributes to the decrease in cholesterol absorption after plant stanol consumption. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020801 |
| Improved method for the synthesis of trans-feruloyl-beta-sitostanol. | Journal of agricultural and food chemistry 20011001 |
| Plant stanol fatty acid esters inhibit cholesterol absorption and hepatic hydroxymethyl glutaryl coenzyme A reductase activity to reduce plasma levels in rabbits. | Metabolism: clinical and experimental 20010901 |
| Effects of diets enriched with two different plant stanol ester mixtures on plasma ubiquinol-10 and fat-soluble antioxidant concentrations. | Metabolism: clinical and experimental 20010501 |
| The hypocholesterolaemic effects of sitostanol in the guinea pig are in part related to changes in hepatic lipids and lipoprotein composition. | The British journal of nutrition 20010201 |
| Effects of plant sterols and stanols on lipid metabolism and cardiovascular risk. | Nutrition, metabolism, and cardiovascular diseases : NMCD 20010201 |
| Assessing plasma pharmacokinetics of cholesterol following oral coadministration with a novel vegetable stanol mixture to fasting rats. | Journal of pharmaceutical sciences 20010101 |
| Identification of a gene, ABCG5, important in the regulation of dietary cholesterol absorption. | Nature genetics 20010101 |
| Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. | Journal of agricultural and food chemistry 20010101 |
| [Plants sterols and stanols: new prospects in prevention of ischemic heart disease (based on data published in the European Heart Journal, 1999, vol. 1 (Suppl S))]. | Terapevticheskii arkhiv 20010101 |
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