| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:25:11 UTC |
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| Updated at | 2020-12-07 19:07:07 UTC |
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| CannabisDB ID | CDB000111 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Stigmasta-4,22-dien-3-one |
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| Description | Stigmasta-4,22-dien-3-one or 4,22-Cholestadien-24-ethyl-3-one 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. The biosynthesis of sterols shares several steps with that of triterpenes and it occurs through the mevalonic acid pathway (MVA; PMID:17467679 ), located mainly in the cytoplasm. A key intermediate in the biosynthesis of sterols is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield the tetracyclic structure typical of the stigmastane skeleton. Stigmasta-4,22-dien-3-one is a neutral compound. Stigmasta-4,22-dien-3-one is one of a small number of phytosteroids (including sitosterol, campesterol, and stigmasterol) that are found in cannabis plants (PMID: 6991645 ). Seven compounds, including stigmasta-4,22-dien-3-one, were isolated from crude extracts of the leaves, stems and roots of Alchornea cordifolia (Schumach. and Thonn.) Müll. Arg. All compounds had antibacterial activity against pathogens of the gastrointestinal, skin, respiratory and urinary tract (PMID: 26724423 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C29H46O |
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| Average Molecular Weight | 410.69 |
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| Monoisotopic Molecular Weight | 410.3549 |
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| IUPAC Name | (1R,2R,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| Traditional Name | (1R,2R,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| CAS Registry Number | 20817-72-5 |
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| SMILES | CC[C@H](C=C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C |
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| InChI Identifier | InChI=1S/C29H46O/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/h8-9,18-21,24-27H,7,10-17H2,1-6H3/t20-,21-,24+,25-,26+,27-,28+,29-/m1/s1 |
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| InChI Key | MKGZDUKUQPPHFM-MEVQFFCQSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Role | Industrial application: |
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| 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 ]
- Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
- Noundou XS, Krause RW, van Vuuren SF, Ndinteh DT, Olivier DK: Antibacterial effects of Alchornea cordifolia (Schumach. and Thonn.) Mull. Arg extracts and compounds on gastrointestinal, skin, respiratory and urinary tract pathogens. J Ethnopharmacol. 2016 Feb 17;179:76-82. doi: 10.1016/j.jep.2015.12.043. Epub 2015 Dec 24. [PubMed:26724423 ]
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