Record Information |
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Version | 1.0 |
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Created at | 2020-03-18 23:24:10 UTC |
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Updated at | 2020-12-07 19:07:04 UTC |
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CannabisDB ID | CDB000084 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Safranal |
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Description | Safranal belongs to the class of organic compounds known as organic oxides which contain an oxide group. Safranal is a neutral compound. Safranal is a component of saffron (PMID: 28705037 ), the spice made from drying the stigmas and styles of crocus flowers (Crocus sativus). Safranal, the constituent primarily responsible for the aroma of saffron, has a sweet, fresh, and herbal taste and is a flavouring ingredient. Safranal has been detected in cauliflowers, cumin seeds, elderberry, figs, lemon, rooibos, saffrons, wolfberry, and tea leaf making safranal a potential biomarker for the consumption of these foods. Safranal is found in cannabis plants (PMID:6991645 ). Safranal is an effective anticonvulsant (PMID: 29609687 ) shown to act as an agonist at the gamma aminobutyric acid (GABA)A-benzodiazepine receptor complex (PMID: 16707256 ). Safranal also exhibits high antioxidant and free radical scavenging activity (PMID: 16317646 ), along with cytotoxicity towards cancer cells in vitro (PMID: 8620447 ). It has also been shown to have antidepressant properties (PMID: 15341662 ). |
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Structure | |
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Synonyms | Value | Source |
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(2,6,6-Trimethylcyclohexa-1,3-dienyl)methanal | ChEBI | 1,1,3-Trimethyl-2-formylcyclohexa-2,4-diene | ChEBI | 2,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde | ChEBI | 2,6,6-Trimethylcyclohexa-1,3-dienyl methanal | ChEBI | Dehydro-beta-cyclocitral | ChEBI | Dehydro-b-cyclocitral | Generator | Dehydro-β-cyclocitral | Generator | 1-Formyl-2,6,6-trimethyl-1,3-cyclohexadiene | HMDB | 2,3-dihydro-2,2,6-Trimethylbenzaldehyde | HMDB | 2,6,6-Trimethyl-1,3-cyclohexadienal | HMDB | 2,6,6-Trimethyl-1,3-cyclohexadiene-1-carbaldehyde | HMDB | 2,6,6-Trimethyl-1,3-cyclohexadienecarboxaldehyde, 9ci | HMDB | FEMA 3389 | HMDB |
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Chemical Formula | C10H14O |
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Average Molecular Weight | 150.22 |
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Monoisotopic Molecular Weight | 150.1045 |
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IUPAC Name | 2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde |
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Traditional Name | safranal |
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CAS Registry Number | 116-26-7 |
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SMILES | CC1=C(C=O)C(C)(C)CC=C1 |
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InChI Identifier | InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 |
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InChI Key | SGAWOGXMMPSZPB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organic oxides |
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Sub Class | Not Available |
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Direct Parent | Organic oxides |
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Alternative Parents | |
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Substituents | - Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic 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 | < 25 °C | Not Available | Boiling Point | 70 °C at 1 mmHg | Wikipedia | 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 | Safranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0kg9-2900000000-b082ebe4ee4447dc7980 | Spectrum | Predicted GC-MS | Safranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Safranal, 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 | splash10-0udi-0900000000-b34ca14deaad2e3be8c4 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxr-9700000000-317a87cd8595a79b42d0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9100000000-2993b4b7b24364148faf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-e83c23e4fe0dedd738e7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-648f823a03c6712751e0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05ng-8900000000-b0e87ace4983e8eca515 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-b7cb4601ae2fb08997c1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dj-0900000000-449dca9897e0f3209324 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-0900000000-861947f0491f909a2588 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0zfr-4900000000-f591f9acd9c148c93dd0 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9800000000-066e7f2d59fb906577f8 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ar0-9300000000-c8eb85059ddf025ee54a | 2021-09-24 | 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 | |
Gamma-aminobutyric acid receptor subunit alpha-1 | GABRA1 | 5q34-q35 | P14867 | details | Gamma-aminobutyric acid receptor subunit alpha-2 | GABRA2 | 4p12 | P47869 | details |
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Metal Bindings | Not Available |
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Receptors | |
Gamma-aminobutyric acid type B receptor subunit 1 | GABBR1 | 6p21.31 | Q9UBS5 | details | Gamma-aminobutyric acid receptor subunit alpha-1 | GABRA1 | 5q34-q35 | P14867 | details | Gamma-aminobutyric acid receptor subunit alpha-2 | GABRA2 | 4p12 | P47869 | details | Taste receptor type 1 member 3 | TAS1R3 | 1p36.33 | Q7RTX0 | details | Taste receptor type 1 member 2 | TAS1R2 | 1p36.13 | Q8TE23 | details |
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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 | HMDB0036061 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB014884 |
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KNApSAcK ID | C00035737 |
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Chemspider ID | 55000 |
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KEGG Compound ID | C17062 |
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BioCyc ID | CPD-8669 |
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BiGG ID | Not Available |
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Wikipedia Link | Safranal |
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METLIN ID | Not Available |
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PubChem Compound | 61041 |
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PDB ID | Not Available |
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ChEBI ID | 53169 |
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References |
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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 ]
- Rameshrad M, Razavi BM, Hosseinzadeh H: Saffron and its derivatives, crocin, crocetin and safranal: a patent review. Expert Opin Ther Pat. 2018 Feb;28(2):147-165. doi: 10.1080/13543776.2017.1355909. Epub 2017 Jul 18. [PubMed:28705037 ]
- Bo-Qiang L, Si-Tong Z, Zu-Yuan L, Wan-Yun N, Bin C, Yuan L, Xuyun L, Liangen M, You-Chao C, Xin-Zhen Y, Zhong C, Xiao-Ying Y, Wei-Wei H: Safranal carried by nanostructured lipid vehicles inhibits generalized epilepsy in mice. Pharmazie. 2018 Apr 2;73(4):207-212. doi: 10.1691/ph.2018.7310. [PubMed:29609687 ]
- Hosseinzadeh H, Sadeghnia HR: Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems. Phytomedicine. 2007 Apr;14(4):256-62. doi: 10.1016/j.phymed.2006.03.007. Epub 2006 May 16. [PubMed:16707256 ]
- Assimopoulou AN, Sinakos Z, Papageorgiou VP: Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents. Phytother Res. 2005 Nov;19(11):997-1000. doi: 10.1002/ptr.1749. [PubMed:16317646 ]
- Escribano J, Alonso GL, Coca-Prados M, Fernandez JA: Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro. Cancer Lett. 1996 Feb 27;100(1-2):23-30. doi: 10.1016/0304-3835(95)04067-6. [PubMed:8620447 ]
- Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F: Comparison of Crocus sativus L. and imipramine in the treatment of mild to moderate depression: a pilot double-blind randomized trial [ISRCTN45683816]. BMC Complement Altern Med. 2004 Sep 2;4:12. doi: 10.1186/1472-6882-4-12. [PubMed:15341662 ]
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