| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:23:22 UTC |
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| Updated at | 2020-11-18 16:34:43 UTC |
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| CannabisDB ID | CDB000062 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Campesterol |
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| Description | Campesterol belongs to the class of organic compounds known as ergosterols which are steroids containing ergosta-5,7,22-trien-3beta-ol on the 3-beta-hydroxylated ergostane skeleton. Thus, campesterol is a sterol lipid which is very hydrophobic, practically insoluble in water, and relatively neutral. Campesterol is a phytosterol, meaning it is a steroid derived from plants. Campesterol is found in highest concentrations in canola, corn and rapeseed and in a lower concentrations in banana, pomegranate, pepper, coffee, grapefruit, cucumber, onion, oat, potato, and lemon grass, making campesterol a potential biomarker for the consumption of these foods. Campesterol is also found in cannabis plants (PMID:6991645 ). As a food additive, phytosterols have cholesterol-lowering properties, by reducing cholesterol absorption in intestines. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols. These products are marketed towards people with high cholesterol, wanting to lower it though diet. and may act in cancer prevention. Phytosterols occur in small amounts 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 reduced cholesterol in human subjects by up to 15% (PMID: 12911045 ) by inhibiting the incorporation of cholesterol into micelles in the gastrointestinal tract, decreasing the overall amount of cholesterol absorbed. This helps to control the body’s total cholesterol levels, as well as modify HDL, LDL and TAG levels. It is also thought that phytosterols may contribute to the Transintestinal Cholesterol Excretion (TICE) pathway and may alter the conversion of bile acids into secondary bile acids, all pathways reducing cholesterol levels (PMID: 31438826 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C28H48O |
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| Average Molecular Weight | 400.69 |
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| Monoisotopic Molecular Weight | 400.3705 |
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| IUPAC Name | (1R,2R,5S,10S,11R,14S,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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| Traditional Name | (1R,2R,5S,10S,11R,14S,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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| CAS Registry Number | 474-62-4 |
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| SMILES | CC(C)[C@H](C)CC[C@@H](C)[C@@H]1CC[C@@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C |
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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-NHCUBAMHSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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|
Not Available | | Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- Katan MB, Grundy SM, Jones P, Law M, Miettinen T, Paoletti R: Efficacy and safety of plant stanols and sterols in the management of blood cholesterol levels. Mayo Clin Proc. 2003 Aug;78(8):965-78. doi: 10.4065/78.8.965. [PubMed:12911045 ]
- Cedo L, Farras M, Lee-Rueckert M, Escola-Gil JC: Molecular Insights into the Mechanisms Underlying the Cholesterol- Lowering Effects of Phytosterols. Curr Med Chem. 2019;26(37):6704-6723. doi: 10.2174/0929867326666190822154701. [PubMed:31438826 ]
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