Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:10:29 UTC
Primary IDFDB002412
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTangeritin
DescriptionTangeritin 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.
CAS Number481-53-8
Structure
Thumb
Synonyms
SynonymSource
4',5,6,7,8-PentamethoxyflavoneChEBI
5,6,7,8,4'-PentamethoxyflavoneChEBI
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
TangeritinChEBI
4',5,6,7,8-Pentamethoxy-flavoneHMDB, MeSH
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4-benzopyroneHMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
Flavone, 4',5,6,7,8-pentamethoxy- (7ci,8ci)HMDB
Flavone, 5,6,7,8,4'-pentamethoxyHMDB
PentamethoxyflavoneHMDB
PonkanetinHMDB
Tangeretin (6ci)HMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-onebiospider
Flavone, 4',5,6,7,8-pentamethoxy-biospider
Flavone, 4',5,6,7,8-pentamethoxy- (7CI,8CI)biospider
Tangeretindb_source
Tangeretin (6CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP2.88ALOGPS
logP2.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)15.26ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.29 m³·mol⁻¹ChemAxon
Polarizability38.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20O7
IUPAC name5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=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
InChI KeyULSUXBXHSYSGDT-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1
Average Molecular Weight372.3686
Monoisotopic Molecular Weight372.120902994
Classification
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.51%; H 5.41%; O 30.08%DFC
Melting PointMp 154°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTangeritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-0229000000-e6e9ad7413b10f4d2f60Spectrum
Predicted GC-MSTangeritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-ee2b46e43857d53e36ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ue9-0958000000-95f79379a8770cf234f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0952000000-385e0c59e575279d19292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0962000000-4ce20f8bebfb893364c72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0950000000-e79b83fbcdc12ca4342b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0972000000-83a368b34c5d8037313d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f6t-0092000000-92f00f21de9842c778222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-a7c011cb08d063f98b3f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-a7c8c2980e91305fecf42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-5acd0f1ad174af992dfb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000t-0009000000-35763dc54f1cba9960fd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-557dbb4d489762f5c6c42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-e5388c8cb4caef8a83982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-052f-0009000000-59afa2bdabbf2a62b6ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4l-0009000000-8f99cd4efaf456f16bd12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0579000000-a6a3232db05025b3a8ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0359000000-37d7e88884dbac30de102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-0489000000-2315290c34940c8911af2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-006x-0009000000-ade42d3073bd96a1c4e12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-af49c5c40b1713ce986a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-ed0776ee5a241620324c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-0249000000-1ea96f27298b5874e53b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-297810d36d9613c636c82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-f9cba6ad31aa4a2c1f912015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1269000000-2c95b789a68359ce6e702015-04-25View Spectrum
NMRNot Available
ChemSpider ID61389
ChEMBL IDCHEMBL73930
KEGG Compound IDC10190
Pubchem Compound ID68077
Pubchem Substance IDNot Available
ChEBI ID9400
Phenol-Explorer ID238
DrugBank IDNot Available
HMDB IDHMDB30539
CRC / DFC (Dictionary of Food Compounds) IDCLQ65-R:CLQ65-R
EAFUS IDNot Available
Dr. Duke IDTANGERITIN|TANGERETIN|PONKANETIN
BIGG IDNot Available
KNApSAcK IDC00001105
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-allergic50857 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 histaminic37956 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-lymphocyticAn antibody that targets T cells, used to prevent rejection in organ transplantation and treat autoimmune diseases by suppressing the immune system.DUKE
Anti metastatic35610 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-mutagenicAn 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-oxidant22586 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 proliferantAn 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
ApoptoticAn 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 preventive35610 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 inhibitor23924 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 inhibitor23924 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
Fungicide24127 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
HypolipidemicAn 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 inhibitor35222 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
Neuroprotective63726 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. 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
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.