Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:04 UTC |
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Update date | 2020-09-17 15:31:15 UTC |
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Primary ID | FDB006298 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Phytosterol |
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Description | Beta-sitosterol, also known as sitosterol or harzol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Beta-sitosterol is widely distributed in the plant kingdom and is a main dietary phytosterol (a plant sterol) found in vegetable oils, nuts, avocados and prepared foods, such as salad dressings. Phytopharmacological extracts, commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea, contain mixtures of phytosterols, that includes Beta-sitosterol. However, these extracts also contain some sterols bonded with glucosides. While beta-sitosterol is the purported active constituent, beta-sitosterol-beta-D-glucoside is often detected. Thus, one or both metabolites may be the active components. Phytosterols, like cholesterol, contain double bonds that are susceptible to oxidation. Beta-sitosterol may have anti-carcinogenic and anti-atherogenic properties (PMID: 13129445, 11432711). Benign prostatic hyperplasia patients treated with beta-sitosterol, compared with placebo, had improved urinary symptom scores and flow measures (PMID: 10368239). Hyperandrogenic postmenopausal women, with higher risk of breast cancer because of their endocrine profiles, were placed on a plant food-based diet, to determine if eating a plant-based diet, rich in phytosterols, rather than animal-based diet, would have an increase in serum phytosterols. Compared to controls, women placed on the plant-based diet had increased serum phytosterols, particularly beta-sitosterol, suggesting that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID: 14652381). Beta-sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID: 12579296). Although the exact mechanism of action of beta-sitosterols in the above studies is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). |
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CAS Number | 83-46-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-beta-Sitosterol | ChEBI | (24R)-Ethylcholest-5-en-3beta-ol | ChEBI | (24R)-Stigmast-5-en-3beta-ol | ChEBI | (3beta)-Stigmast-5-en-3-ol | ChEBI | 22,23-Dihydrostigmasterol | ChEBI | 24alpha-Ethylcholesterol | ChEBI | alpha-Dihydrofucosterol | ChEBI | Azuprostat | ChEBI | beta-Sitosterin | ChEBI | Cupreol | ChEBI | Nimbosterol | ChEBI | Triastonal | ChEBI | Sitosterol | Kegg | Harzol | Kegg | (-)-b-Sitosterol | Generator | (-)-Β-sitosterol | Generator | (24R)-Ethylcholest-5-en-3b-ol | Generator | (24R)-Ethylcholest-5-en-3β-ol | Generator | (24R)-Stigmast-5-en-3b-ol | Generator | (24R)-Stigmast-5-en-3β-ol | Generator | (3b)-Stigmast-5-en-3-ol | Generator | (3Β)-stigmast-5-en-3-ol | Generator | 24a-Ethylcholesterol | Generator | 24Α-ethylcholesterol | Generator | a-Dihydrofucosterol | Generator | Α-dihydrofucosterol | Generator | b-Sitosterin | Generator | Β-sitosterin | Generator | b-Sitosterol | Generator | Β-sitosterol | Generator | 24-Ethylcholest-5-en-3 beta-ol | HMDB | 24-Ethylcholesterol | HMDB | 3beta-Sitosterol | HMDB | 3beta-Stigmast-5-en-3-ol | HMDB | Clionasterol | HMDB | Sitosterol, (3beta)-isomer | HMDB | 22,23-Dihydro-stigmasterol | HMDB | a-Phytosterol | HMDB | alpha-Phytosterol | HMDB | Angelicin | HMDB | beta-Phytosterol | HMDB | Cinchol | HMDB | D5-Stigmasten-3b-ol | HMDB | Delta5-Stigmasten-3b-ol | HMDB | Phytosterol | HMDB | Prostasal | HMDB | Quebrachol | HMDB | Rhamnol | HMDB | Sito-lande | HMDB | Sobatum | HMDB | Stigmast-5-en-3-ol | HMDB | Stigmast-5-en-3b-ol | HMDB | Stigmast-5-en-3beta-ol | HMDB | Stigmast-5-en-3β-ol | HMDB | delta5-Stigmasten-3beta-ol | HMDB | Δ5-stigmasten-3β-ol | HMDB | Α-phytosterol | HMDB | Rhammol | HMDB | Δ5-stigmasten-3beta-ol | HMDB | beta-Sitosterol | ChEBI | Phytosterols | manual | Plant sterols | manual |
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Predicted Properties | |
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Chemical Formula | C29H50O |
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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 |
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InChI Identifier | 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 |
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InChI Key | KZJWDPNRJALLNS-VJSFXXLFSA-N |
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Isomeric 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)CC[C@@H](CC)C(C)C |
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Average Molecular Weight | 414.718 |
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Monoisotopic Molecular Weight | 414.38616623 |
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Classification |
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Description | Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Stigmastanes and derivatives |
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Direct Parent | Stigmastanes and derivatives |
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Alternative Parents | |
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Substituents | - C24-propyl-sterol-skeleton
- Stigmastane-skeleton
- Triterpenoid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-052f-9821000000-0f43ba6def9281d5c86d | 2015-03-01 | View Spectrum | GC-MS | Phytosterol, 1 TMS, GC-MS Spectrum | splash10-054k-3912000000-22f633cd1bdd2ecca960 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-0aor-9810000000-ab4d6cb3490b23c5cb70 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-03di-5947700000-fe0573c7669e97c469f5 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-0002-2931000000-0d63e91b728deb1446a4 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-0a4l-9822000000-2be95863c114e7cd2597 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-0a4l-9601000000-edade780f6cfb8ddc7d1 | Spectrum | GC-MS | Phytosterol, non-derivatized, GC-MS Spectrum | splash10-054k-3912000000-22f633cd1bdd2ecca960 | Spectrum | Predicted GC-MS | Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052v-1109000000-2eef6dd56a6c52421610 | Spectrum | Predicted GC-MS | Phytosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-4103900000-a09c1c265657e57bd096 | Spectrum | Predicted GC-MS | Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phytosterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-0002900000-f2b81675160568c483c5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-05nb-3930100000-897e65b10be8a412585c | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a59-6900000000-b62b8d1bd807fc41256b | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-0aor-9810000000-fcbfd841778e213b3d3e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-03di-5947700000-4234b723ccdb0e25d290 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive | splash10-0002-2931000000-b2156fbd63c29312b076 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0a4l-9822000000-2be95863c114e7cd2597 | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0019500000-b9eddfa8d56747167ada | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kb-5139100000-42d184a108f9e994dc01 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-9076000000-54ef98673160128cbacd | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-158617c2e43f1a46b58a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0004900000-632250471791929b07e3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-2019000000-717c6229722cf73f3faa | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000900000-eda302082c5114b2ab3a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0001900000-86165feb8e32cd8692ad | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-0001900000-1fc08db7654e3c4918f9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-4117900000-f005f19377309e9fb82d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06du-9146100000-d28aeb2182048e0912fa | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9511000000-ff6bd6e1f8902e32555d | 2021-09-22 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 26125 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | PHYTOSTEROL|PHYTOSTEROLS |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Phytosterol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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