| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:13 UTC |
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| Update date | 2019-11-26 03:06:57 UTC |
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| Primary ID | FDB012521 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Campesterol |
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| Description | Constituent of rapeseed oil (Brassica napa), soybean oil (Glycine max) and wheatgerm oil (Triticum subspecies). Found in virtually all plant oils
Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%.; ; The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia; Presence of brassicasterol, together with auxiliary markers ?-linolenic acid and erucic acid, is a marker of adulteration of soybean oil and sunflower oil with rapeseed oil. As there is no brassicasterol in sunflower and soybean oil, but its concentration in rapeseed oil is about 1400 mg/kg, the amount of rapeseed oil added can be calculated. |
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| CAS Number | 474-62-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C28H48O |
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| IUPAC name | (2R,5S,15R)-14-[(2R,5R)-5,6-dimethylheptan-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/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23?,24?,25?,26?,27+,28-/m1/s1 |
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| InChI Key | SGNBVLSWZMBQTH-MMTVXVTESA-N |
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| Isomeric SMILES | CC(C)[C@H](C)CC[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C |
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| Average Molecular Weight | 400.6801 |
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| Monoisotopic Molecular Weight | 400.370516158 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. |
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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 | Ergostane steroids |
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| Direct Parent | Ergosterols and derivatives |
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| Alternative Parents | |
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| Substituents | - Ergosterol-skeleton
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 83.93%; H 12.07%; O 3.99% | DFC |
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| Melting Point | Mp 157-158° | DFC |
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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 | [a]23D -33 (CHCl3) | DFC |
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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 | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-1019500000-05a81f76ea60f47816b3 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lj-7149100000-434088453bcde1b45575 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-8093000000-5277512d6dbbe5d1ce17 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-cd4af4f76d04e1cacf46 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-4bea7e37de9105dc8905 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00lr-3019000000-9b243f6f924e30b0b732 | 2017-06-28 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 4446730 |
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| ChEMBL ID | CHEMBL485421 |
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| KEGG Compound ID | C01789 |
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| Pubchem Compound ID | 5283637 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 28623 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02869 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HHR44-Q:HHR45-R |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | CAMPESTEROL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003647 |
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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 | Campesterol |
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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 | | Descriptor | ID | Definition | Reference |
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| antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | | hypocholesterolemic | | | DUKE |
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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 | show |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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