(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

• ChemBase ID: 72928
• Molecular Formular: C29H50O
• Molecular Mass: 414.7067
• Monoisotopic Mass: 414.38616622
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CC[C@@H](CC)C(C)C)C)C)O
• Canonical 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]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
• InChI: InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: KZJWDPNRJALLNS-VJSFXXLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: β-sitosterol
• Synonyms: α-Dihydrofucosterol; 24β-Ethylcholesterol; 5-Stigmasten-3β-ol; β-SITOSTEROL; β-Sitosterol; 22,23-Dihydrostigmasterol; Stigmast-5-en-3-ol; β-Sitosterin; Beta-Sitosterol; β-Sitosterol; α-二氢岩藻甾醇; 22,23-二氢豆甾醇; 24β-乙基胆固醇; 5-豆甾烯-3β-醇; β-谷甾醇

Database IDs

• CAS Number: 83-46-5
• EC Number: 271-413-3; 200-663-8; 201-480-6
• MDL Number: MFCD00003631
• Beilstein Number: 1916165
• PubChem SID: 24899671; 24870722; 162037848; 24899468; 24899862
• PubChem CID: 222284
• CHEBI ID: 27693
• CHEMBL: 221542
• Chemspider ID: 192962
• Unique Ingredient Identifier: S347WMO6M4
• Wikipedia Title: Beta-Sitosterol

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.8444767
• LogD (pH = 7.4): 7.8444767
• Log P: 7.8444767
• Molar Refractivity: 129.7661 cm^3
• Polarizability: 51.670784 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble20 mg/mL, clear, colorless
• Apperance: Powder
• Melting Point: 136-140 °C(lit.); 136–140 °C
• Optical Rotation: [α]25/D -37°, c = 2 in chloroform

Safety Information

• Storage Condition: -20°C
• RTECS: WJ2600000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 1888
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-38-40-48/20/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H351-H373
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1888 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥40%; ≥70%; ≥90% (GC); ≥95%; ≥97%; ≥97.0% (GC); 40%
• Concentration: 100 μg/mL in chloroform
• Grade: analytical standard
• Salt Data: Free Base
• Packaging: ampule of 1 mL
• Impurities: campesterol and β-sitostanol, residual
• Biological Source: from soybean; synthetic
• Empirical Formula (Hill Notation): C29H50O

DETAILS

Selleck Chemicals - S2273

Research Area: Cardiovascular Disease
Biological Activity:
β-sitosterol reduces blood levels of cholesterol, and is sometimes used in treating hypercholesterolemia. β-Sitosterol inhibits cholesterol absorption in the intestine. When the sterol is absorbed in the intestine, it is transported by lipoproteins and incorporated into the cellular membrane. Phytosterols and phytostanols both inhibit the uptake of dietary and biliary cholesterol, decreasing the levels of LDL and serum total cholesterol. [1][2]

Sigma Aldrich - S9889

Biochem/physiol Actions
Plant derived estrogen
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S9889.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 85451

Packaging
100 g in poly bottle

Sigma Aldrich - S1270

Biochem/physiol Actions
A phytosterol with structure very similar to cholesterol that exhibits estrogenic activity. Inhibits proliferation of human leukemia cells, with G2/M arrest, endoreduplication, and polymerization of α-tubulin and microtubules.1

Sigma Aldrich - S5753

Quality
实习用经 13C-NMR 检测证实还含有菜油甾醇和二氢芜莆甾醇。1,2

REFERENCES

• Matsuoka K et al. Chem Phys Lipids. 2008 Aug;154(2):87-93.