| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:47:46 UTC |
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| Updated at | 2020-11-18 16:35:21 UTC |
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| CannabisDB ID | CDB000633 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Methacrylic anhydride |
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| Description | Methacrylic anhydride, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing two carboxylic acid groups. Methacrylic anhydride is a liquid which reacts exothermically with water. It can also react with hydroxyl- and amino-groups present in some organic compounds leading to covalent attachment of methacryloyl moieties. These functional groups could be successfully used either in subsequent polymerisation or reactions with thiols. For example, chitosan modified by methacryloylation exhibits better ability to adhere to mucosal surfaces (mucoadhesion) due to its reactivity with thiol groups present in cysteine domains of mucins (PMID: 30130604 ). Methacrylic anhydride it has been reported to be a volatile component of cannabis samples (PMID: 26657499 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C8H10O3 |
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| Average Molecular Weight | 154.17 |
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| Monoisotopic Molecular Weight | 154.063 |
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| IUPAC Name | 2-methylprop-2-enoyl 2-methylprop-2-enoate |
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| Traditional Name | methacrylic anhydride |
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| CAS Registry Number | 760-93-0 |
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| SMILES | CC(=C)C(=O)OC(=O)C(C)=C |
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| InChI Identifier | InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3 |
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| InChI Key | DCUFMVPCXCSVNP-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Dicarboxylic acids and derivatives |
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| Direct Parent | Dicarboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Dicarboxylic acid or derivatives
- Carboxylic acid anhydride
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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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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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Methacrylic anhydride, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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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 | splash10-0a4i-0900000000-64dac1edb40becfdc4be | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4l-7900000000-bc4e024d8d27ea29ab5e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-8a1c60cb3c5bc97bab3f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-c6e763550aea81909164 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-2fcb37b0636ba483984a | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udr-3900000000-317df58c88ea3a28e46a | 2016-08-03 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Not Available |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 12974 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| General References | - Kolawole OM, Lau WM, Khutoryanskiy VV: Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery. Int J Pharm. 2018 Oct 25;550(1-2):123-129. doi: 10.1016/j.ijpharm.2018.08.034. Epub 2018 Aug 18. [PubMed:30130604 ]
- Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
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