Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:50:02 UTC |
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Updated at | 2020-12-07 19:07:39 UTC |
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CannabisDB ID | CDB000667 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Salicyladehyde |
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Description | Salicyladehyde or 2-Hydroxybenzaldehyde, also known as salicylal or o-formylphenol, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Salicylaldehyde is a colorless oily liquid. At high concentrations it has a bitter almond odor. In nature, salicylaldehyde has been identified as the metabolite responsible for the characteristic aroma of buckwheat (PMID: 26003350 ). It is also a component of castoreum, used in perfumery (PMID: 24249178 ). The defensive secretions of some leaf beatle species, such as the red poplar leaf beetle, also contain salicylaldehyde (PMID: 27033853 ). It has also been detected in the volatile fraction of Cannabis sativa samples (PMID: 26657499 ). Salicyladehyde is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). |
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Structure | |
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Synonyms | Value | Source |
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O-Formylphenol | ChEBI | O-Hydroxybenzaldehyde | ChEBI | Salicylal | ChEBI | Salicylaldehyd | ChEBI | Salizylaldehyd | ChEBI | 2-Formylphenol | HMDB | FEMA 3004 | HMDB | Salicylaldehyde, 8ci | HMDB | Salicylic aldehyde | HMDB | 2-Hydroxybenzaldehyde | ChEBI | Salicylaldehyde ester | MeSH | 2-Hydroxy-1-benzaldehyde | HMDB | Salicylaldehyde | HMDB |
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Chemical Formula | C7H6O2 |
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Average Molecular Weight | 122.12 |
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Monoisotopic Molecular Weight | 122.0368 |
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IUPAC Name | 2-hydroxybenzaldehyde |
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Traditional Name | salicylaldehyde |
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CAS Registry Number | 90-02-8 |
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SMILES | OC1=CC=CC=C1C=O |
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InChI Identifier | InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H |
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InChI Key | SMQUZDBALVYZAC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Hydroxybenzaldehydes |
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Alternative Parents | |
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Substituents | - Hydroxybenzaldehyde
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Organic oxide
- Hydrocarbon derivative
- 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: Biological role: |
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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 | 0.7 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 17 mg/mL at 86 °C | Not Available | logP | 1.81 | 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) | splash10-00di-9600000000-af7c15a0b15606c87955 | 2014-09-20 | View Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-583bbd8c5848ff6c26b1 | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00di-9800000000-e0a9ad2626c3dba695db | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00dr-9500000000-e18d8d6fc6476767e239 | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00kf-3900000000-632e662634ab33df04b6 | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-583bbd8c5848ff6c26b1 | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00di-9800000000-e0a9ad2626c3dba695db | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00dr-9500000000-e18d8d6fc6476767e239 | Spectrum | GC-MS | Salicyladehyde, non-derivatized, GC-MS Spectrum | splash10-00kf-3900000000-632e662634ab33df04b6 | Spectrum | Predicted GC-MS | Salicyladehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-6900000000-f3f3aaf417e6320169c2 | Spectrum | Predicted GC-MS | Salicyladehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9700000000-ad6e9da1650fde48af74 | Spectrum | Predicted GC-MS | Salicyladehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Salicyladehyde, 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 - LC-ESI-QFT , negative | splash10-00di-0900000000-be0f193ffc0b577e05b8 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative | splash10-00di-0900000000-f6bbf793b513247a43f9 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-0900000000-1fd6de1de02ee87b504b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-0900000000-ee44a10727fab869a4d2 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-0900000000-690d3ae60cf893b9ff06 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-0900000000-d8a2c0fadb6a182d8f0a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-00di-2900000000-97030dc87c10651e96a2 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-00dj-5900000000-8d437ad0fdcd47cd7bcb | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-006t-9600000000-f45ab5984169c5818bcb | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00di-0900000000-71123584d3741c4699ab | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-1255ecd1c31ba1344679 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-2900000000-a6ed64aa8049a5f6c188 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-a9b45cf42b4fda665c1d | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-028de9906ead3d0f2c4f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-de8eee3eed47a07dd7d8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fxx-9100000000-8365be7aef3c22b70d98 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05fs-3900000000-5b3e0b81e8c054ff2cf6 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0cdj-9400000000-9a54f9d98b585a8691d9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-23bd778d9581ae5a1f0d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-4900000000-f0356154a12f6010da9e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-d0111d930d0fb38e1292 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9000000000-f94ec230876fa6f26623 | 2021-09-22 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, benzene, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, benzene, 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 | HMDB0034170 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB012456 |
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KNApSAcK ID | C00031273 |
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Chemspider ID | 13863618 |
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KEGG Compound ID | C06202 |
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BioCyc ID | SALICYLALDEHYDE |
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BiGG ID | Not Available |
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Wikipedia Link | Salicylaldehyde |
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METLIN ID | Not Available |
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PubChem Compound | 6998 |
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PDB ID | NK |
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ChEBI ID | 16008 |
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References |
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General References | - Janes D, Kreft S: Salicylaldehyde is a characteristic aroma component of buckwheat groats. Food Chem. 2008 Jul 15;109(2):293-8. doi: 10.1016/j.foodchem.2007.12.032. Epub 2008 Feb 5. [PubMed:26003350 ]
- Tang R, Webster FX, Muller-Schwarze D: Phenolic compounds from male castoreum of the North American beaver,Castor canadensis. J Chem Ecol. 1993 Jul;19(7):1491-500. doi: 10.1007/BF00984892. [PubMed:24249178 ]
- Pauls G, Becker T, Rahfeld P, Gretscher RR, Paetz C, Pasteels J, von Reuss SH, Burse A, Boland W: Two Defensive Lines in Juvenile Leaf Beetles; Esters of 3-nitropropionic Acid in the Hemolymph and Aposematic Warning. J Chem Ecol. 2016 Mar;42(3):240-8. doi: 10.1007/s10886-016-0684-0. Epub 2016 Mar 31. [PubMed:27033853 ]
- 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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