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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:30 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030539
Secondary Accession Numbers
  • HMDB30539
Metabolite Identification
Common 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 mandarin orange (clementine, tangerine), broccolis (Brassica oleracea var. italica), green tea, sweet bays (Laurus nobilis), and black tea. This could make tangeritin a potential biomarker for the consumption of these foods. Tangeritin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Tangeritin.
Structure
Data?1563862001
Synonyms
ValueSource
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
Chemical FormulaC20H20O7
Average Molecular Weight372.3686
Monoisotopic Molecular Weight372.120902994
IUPAC Name5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nametangeretin
CAS Registry Number481-53-8
SMILES
COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1
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
InChI KeyULSUXBXHSYSGDT-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 °CNot Available
Boiling Point565.00 to 566.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility8.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.788 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker187.90530932474
[M+H]+Not Available184.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00001480
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.30731661259
DarkChem[M-H]-188.83831661259
DeepCCS[M+H]+181.28130932474
DeepCCS[M-H]-178.92330932474
DeepCCS[M-2H]-212.82830932474
DeepCCS[M+Na]+188.05630932474
AllCCS[M+H]+187.732859911
AllCCS[M+H-H2O]+184.632859911
AllCCS[M+NH4]+190.632859911
AllCCS[M+Na]+191.432859911
AllCCS[M-H]-192.032859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-192.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TangeritinCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O14614.7Standard polar33892256
TangeritinCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O13185.7Standard non polar33892256
TangeritinCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O13210.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tangeritin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0229000000-e6e9ad7413b10f4d2f602017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tangeritin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-0udi-0009000000-ee2b46e43857d53e36ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-0ue9-0958000000-95f79379a8770cf234f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-001i-0952000000-385e0c59e575279d19292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-001i-0962000000-4ce20f8bebfb893364c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-001i-0950000000-e79b83fbcdc12ca4342b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-001i-0972000000-83a368b34c5d8037313d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , negative-QTOFsplash10-0f6t-0092000000-92f00f21de9842c778222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-a7c011cb08d063f98b3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-a7c8c2980e91305fecf42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-5acd0f1ad174af992dfb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-000t-0009000000-35763dc54f1cba9960fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-557dbb4d489762f5c6c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-e5388c8cb4caef8a83982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-052f-0009000000-59afa2bdabbf2a62b6ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin Linear Ion Trap , positive-QTOFsplash10-0a4l-0009000000-8f99cd4efaf456f16bd12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin , positive-QTOFsplash10-0006-0579000000-a6a3232db05025b3a8ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin , positive-QTOFsplash10-0006-0359000000-37d7e88884dbac30de102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin 40V, Positive-QTOFsplash10-0006-0489000000-2315290c34940c8911af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tangeritin 20V, Positive-QTOFsplash10-006x-0009000000-ade42d3073bd96a1c4e12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 10V, Positive-QTOFsplash10-00di-0009000000-af49c5c40b1713ce986a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 20V, Positive-QTOFsplash10-00di-0009000000-ed0776ee5a241620324c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 40V, Positive-QTOFsplash10-01ox-0249000000-1ea96f27298b5874e53b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 10V, Negative-QTOFsplash10-00di-0009000000-297810d36d9613c636c82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 20V, Negative-QTOFsplash10-00di-0009000000-f9cba6ad31aa4a2c1f912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tangeritin 40V, Negative-QTOFsplash10-0a4l-1269000000-2c95b789a68359ce6e702015-04-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID238
FooDB IDFDB002412
KNApSAcK IDC00001105
Chemspider ID61389
KEGG Compound IDC10190
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTangeritin
METLIN IDNot Available
PubChem Compound68077
PDB IDNot Available
ChEBI ID9400
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1055961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .