Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:48:48 UTC |
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Updated at | 2021-01-04 18:48:56 UTC |
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CannabisDB ID | CDB000648 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | o-Dimethyl hydroquinone |
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Description | 1,2-Dimethoxybenzene, also known as veratrole, o-Dimethylhydroquinone or 2-Methoxyanisole is one of three structural isomers of dimethoxybenzene wherein two methoxy groups are substituted at three positions (the 1,2-, 1,3- and 1,4- positions) of the benzene ring. 1,2-Dimethoxybenzene belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. It is the dimethyl ether derived from pyrocatechol. 1,2-Dimethoxybenzene exists as a clear, colorless liquid and is slightly soluble in water, but miscible in all organic solvents. 1,2-Dimethoxybenzene has a sweet, vanilla, creamy, and musty aroma. It is used as both a flavoring agent and a perfurming agent. 1,2-Dimethoxybenzene has been detected, but not quantified in, several different foods, such as corn, coffee, curry, rice, tea, milk and milk products, broccoli, and green vegetables. 1,2-Dimethoxybenzene is relatively electron-rich and thus readily undergoes electrophilic substitution, making it an ideal building block for the organic synthesis of other aromatic compounds. 1,2-Dimethoxybenzene also functions as an insect attractant for pollinating plants (PMID: 22937972 ). Dimethoxybenzenes are found in cannabis smoke. 1,2-Dimethoxybenzene is formed during the combustion of cannabis ( Ref:DOI ). |
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Structure | |
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Synonyms | Value | Source |
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2-Dimethoxybenzol | ChEBI | 2-Methoxyanisole | ChEBI | Catechol dimethyl ether | ChEBI | Methyl guaiacol | ChEBI | O,O-Dimethyl catechol | ChEBI | O-Dimethoxybenzene | ChEBI | Pyrocatechol dimethyl ether | ChEBI | Veratrole | MeSH | FEMA 3799 | HMDB | Guaiacol methylether | HMDB | O-Dimethoxy-benzene | HMDB | Orthodimethoxybenzene | HMDB | Synthol | HMDB | Veratrol | HMDB | 1,2-Dimethoxybenzene | MeSH |
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Chemical Formula | C8H10O2 |
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Average Molecular Weight | 138.16 |
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Monoisotopic Molecular Weight | 138.0681 |
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IUPAC Name | 1,2-dimethoxybenzene |
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Traditional Name | veratrole |
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CAS Registry Number | 91-16-7 |
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SMILES | COC1=CC=CC=C1OC |
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InChI Identifier | InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 |
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InChI Key | ABDKAPXRBAPSQN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Methoxybenzenes |
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Direct Parent | Dimethoxybenzenes |
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Alternative Parents | |
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Substituents | - O-dimethoxybenzene
- Dimethoxybenzene
- Phenoxy compound
- Phenol ether
- Anisole
- Alkyl aryl ether
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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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 | 22.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | 1.60 | 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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0f9j-9300000000-84232d2a7771f5297e19 | 2015-03-01 | View Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000j-9500000000-ba3df3a0cec54fd4ddb1 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-9600000000-f768976db437187c3fe9 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-0900000000-9ce5b11ff09d03512069 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-7900000000-074bcd0c663f55639243 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000j-9500000000-f6904476f7cfb2482f90 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-0f96-9100000000-82821a5bc5bbc4df87be | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000j-9500000000-ba3df3a0cec54fd4ddb1 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-9600000000-f768976db437187c3fe9 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-0900000000-9ce5b11ff09d03512069 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000i-7900000000-074bcd0c663f55639243 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-000j-9500000000-f6904476f7cfb2482f90 | Spectrum | GC-MS | o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum | splash10-0f96-9100000000-82821a5bc5bbc4df87be | Spectrum | Predicted GC-MS | o-Dimethyl hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-6900000000-3def7a8de562d9ad8c38 | Spectrum | Predicted GC-MS | o-Dimethyl hydroquinone, 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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MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-000i-0900000000-59a80da831843d5184e1 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-000i-0900000000-d543225601eac501e480 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-000i-0900000000-0dc8d9858fc1f6303e92 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-000i-0900000000-2083d26506807f5733cd | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-000i-0900000000-da241afd8465683b4338 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0079-0900000000-6a74d1e3dd466db53877 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0079-0900000000-608cccb6ae052653a61b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-00dr-0900000000-4dd50241a6ad9dc07120 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-00dr-0900000000-2df36af936932591c82d | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-00dr-0900000000-0c8975f2c2c954725d97 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-00di-1900000000-408b3a6fa1dcb4b736b1 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-0ab9-3900000000-37537f5395c7cdd9d04e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-0a4i-6900000000-b34376ed4e790654e616 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, positive | splash10-0a59-9400000000-4b20048c8c78431c945e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, positive | splash10-001i-9100000000-75adf0e079ec008653ec | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 12V, positive | splash10-0f89-9000000000-f5043fce7ffa5ce956c7 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 9V, positive | splash10-00di-0900000000-66be3b4be4fff2fa073b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 9V, positive | splash10-004i-9000000000-a6d296f4cff997d26f26 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 9V, positive | splash10-0a4i-0900000000-551ac0f723bcc2798d25 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-fca0b605e8d5224b20a6 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-065ed98981a51fc3722f | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9300000000-ee666f72073d7c63af1b | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-6dd2938f60d4205e97a6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-1c3155acdb826f8cb385 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ki7-9200000000-9b9c41d6b2a64125ccf0 | 2016-08-03 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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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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External Links |
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HMDB ID | HMDB0032139 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB008865 |
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KNApSAcK ID | C00056272 |
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Chemspider ID | 13861009 |
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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 | Veratrole |
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METLIN ID | Not Available |
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PubChem Compound | 7043 |
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PDB ID | Not Available |
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ChEBI ID | 59114 |
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References |
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General References | - 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 ]
- Gupta AK, Akhtar TA, Widmer A, Pichersky E, Schiestl FP: Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction. BMC Plant Biol. 2012 Aug 31;12:158. doi: 10.1186/1471-2229-12-158. [PubMed:22937972 ]
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