Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:22 UTC |
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Update date | 2020-02-24 19:10:29 UTC |
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Primary ID | FDB002412 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Tangeritin |
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Description | Tangeritin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, tangeritin is considered to be a flavonoid. Tangeritin is a bitter tasting compound. Tangeritin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Tangeritin has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), fruits, broccolis (Brassica oleracea var. italica), mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make tangeritin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Tangeritin. |
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CAS Number | 481-53-8 |
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Structure | |
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Synonyms | Synonym | Source |
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4',5,6,7,8-Pentamethoxyflavone | ChEBI | 5,6,7,8,4'-Pentamethoxyflavone | ChEBI | 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one | ChEBI | Tangeritin | ChEBI | 4',5,6,7,8-Pentamethoxy-flavone | HMDB, MeSH | 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone | HMDB | 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci | HMDB | 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one | HMDB | Flavone, 4',5,6,7,8-pentamethoxy- (7ci,8ci) | HMDB | Flavone, 5,6,7,8,4'-pentamethoxy | HMDB | Pentamethoxyflavone | HMDB | Ponkanetin | HMDB | Tangeretin (6ci) | HMDB | 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI | db_source | 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one | biospider | Flavone, 4',5,6,7,8-pentamethoxy- | biospider | Flavone, 4',5,6,7,8-pentamethoxy- (7CI,8CI) | biospider | Tangeretin | db_source | Tangeretin (6CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C20H20O7 |
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IUPAC name | 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3 |
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InChI Key | ULSUXBXHSYSGDT-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 |
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Average Molecular Weight | 372.3686 |
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Monoisotopic Molecular Weight | 372.120902994 |
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Classification |
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Description | Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | O-methylated flavonoids |
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Direct Parent | 8-O-methylated flavonoids |
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Alternative Parents | |
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Substituents | - 4p-methoxyflavonoid-skeleton
- 5-methoxyflavonoid-skeleton
- 6-methoxyflavonoid-skeleton
- 7-methoxyflavonoid-skeleton
- 8-methoxyflavonoid-skeleton
- Flavone
- Chromone
- Benzopyran
- 1-benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Alkyl aryl ether
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous ester
- Organoheterocyclic compound
- Ether
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 64.51%; H 5.41%; O 30.08% | DFC |
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Melting Point | Mp 154° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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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 | Tangeritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052f-0229000000-e6e9ad7413b10f4d2f60 | Spectrum | Predicted GC-MS | Tangeritin, 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 - Linear Ion Trap , negative | splash10-0udi-0009000000-ee2b46e43857d53e36ea | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0ue9-0958000000-95f79379a8770cf234f4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0952000000-385e0c59e575279d1929 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0962000000-4ce20f8bebfb893364c7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0950000000-e79b83fbcdc12ca4342b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0972000000-83a368b34c5d8037313d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0f6t-0092000000-92f00f21de9842c77822 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-a7c011cb08d063f98b3f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-a7c8c2980e91305fecf4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-5acd0f1ad174af992dfb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000t-0009000000-35763dc54f1cba9960fd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-557dbb4d489762f5c6c4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-e5388c8cb4caef8a8398 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-052f-0009000000-59afa2bdabbf2a62b6ee | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4l-0009000000-8f99cd4efaf456f16bd1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-0579000000-a6a3232db05025b3a8ec | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-0359000000-37d7e88884dbac30de10 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-0489000000-2315290c34940c8911af | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-006x-0009000000-ade42d3073bd96a1c4e1 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0009000000-af49c5c40b1713ce986a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0009000000-ed0776ee5a241620324c | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ox-0249000000-1ea96f27298b5874e53b | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0009000000-297810d36d9613c636c8 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0009000000-f9cba6ad31aa4a2c1f91 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-1269000000-2c95b789a68359ce6e70 | 2015-04-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 61389 |
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ChEMBL ID | CHEMBL73930 |
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KEGG Compound ID | C10190 |
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Pubchem Compound ID | 68077 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 9400 |
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Phenol-Explorer ID | 238 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30539 |
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CRC / DFC (Dictionary of Food Compounds) ID | CLQ65-R:CLQ65-R |
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EAFUS ID | Not Available |
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Dr. Duke ID | TANGERITIN|TANGERETIN|PONKANETIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001105 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-allergic | 50857 | An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies. | DUKE | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | DUKE | Anti-lymphocytic | | An antibody that targets T cells, used to prevent rejection in organ transplantation and treat autoimmune diseases by suppressing the immune system. | DUKE | Anti metastatic | 35610 | An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer. | DUKE | Anti-mutagenic | | An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti proliferant | | An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation. | DUKE | Apoptotic | | An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | ERK1 inhibitor | 23924 | An agent that blocks the activity of ERK1, a key enzyme in cell signaling pathways, reducing cell proliferation and inflammation. Therapeutically, it has applications in cancer, neurodegenerative, and inflammatory diseases, with potential uses in treating tumors, Alzheimer's, and autoimmune disorders. | DUKE | ERK2 inhibitor | 23924 | An agent that blocks the activity of ERK2, a key enzyme in cell signaling pathways, reducing cell proliferation and inflammation. Therapeutically, it has applications in cancer, autoimmune diseases, and neurodegenerative disorders, with potential uses in treating tumors, multiple sclerosis, and Alzheimer's disease. | DUKE | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | Hypolipidemic | | An agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health. | DUKE | Multidrug resistance inhibitor | 35222 | An agent that blocks the efflux pumps in cancer cells, restoring sensitivity to chemotherapy drugs and overcoming drug resistance, commonly used in cancer treatment to enhance efficacy of anticancer medications. | DUKE | Neuroprotective | 63726 | An agent that protects nerve cells from damage or degeneration, reducing the risk of neurodegenerative diseases. Therapeutically, it helps manage conditions like Alzheimer's, Parkinson's, and stroke, promoting neuronal survival and function. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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