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{{chembox |
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{{chembox |
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| verifiedrevid = 444130959 |
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| Name = Tangeritin |
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| verifiedrevid = 444133047 |
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| ImageFile = Tangeritin_structure.png |
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| Name = Tangeretin (Tangeritin) |
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| ImageFile = Tangeritin.svg |
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| ImageName = |
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| ImageSize = 220 |
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| IUPACName = 5,6,7,8-tetramethoxy-2-<br />(4-methoxyphenyl)-4H-<br />1-benzopyran-4-one |
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| ImageAlt = Skeletal formula |
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| Section1 = {{Chembox Identifiers |
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| ImageFile1 = Tangeritin molecule ball.png |
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| CASNo = 481-53-8 |
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| ImageSize1 = 220 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ImageAlt1 = Ball-and-stick model |
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| IUPACName = 4′,5,6,7,8-Pentamethoxyflavone |
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| SystematicName = 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 481-53-8 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 9400 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = I4TLA1DLX6 |
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| UNII = I4TLA1DLX6 |
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| SMILES = O=C2C1=C(OC)C(OC)=C(OC)C(OC)<br />=C1OC(C3=CC=C(OC)C=C3)=C2 |
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| SMILES = O=C2C1=C(OC)C(OC)=C(OC)C(OC)=C1OC(C3=CC=C(OC)C=C3)=C2 |
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| EINECS = 207-570-1 |
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| PubChem = 68077 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 61389 |
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| InChI = 1/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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| InChIKey = ULSUXBXHSYSGDT-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ULSUXBXHSYSGDT-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C10190 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>20</sub>H<sub>20</sub>O<sub>7</sub> |
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| Formula = C<sub>20</sub>H<sub>20</sub>O<sub>7</sub> |
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| MolarMass = 372.37 g/mol |
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| MolarMass = 372.37 g/mol |
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| Density = 1.244 ± 0.06 g/cm<sup>3</sup><ref name="SciFinder">SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).</ref> |
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| MeltingPt = 155-156 °C |
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| Solubility = 0.037 g/L<ref name="SciFinder" /> |
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| BoilingPtC = 565.3 +/- 50.0 |
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| BoilingPt_ref = <ref name="SciFinder" /> |
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| MeltingPtC = 155 to 156 |
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'''Tangeritin''' is an O-] that is found in ] and other ] peels. Tangeritin strengthens the cell wall and protects it from invasion {{Citation needed|date=January 2008}}. |
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'''Tangeretin''' is an O-] that is found in ] and other ] peels. Tangeretin strengthens the cell wall and acts as a plant's defensive mechanism against disease-causing pathogens.<ref name = "Uckoo">Uckoo, RM; et al. Sep. Purif. Technol. 2011.</ref> |
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It has also been used as a marker compound to detect contamination in citrus juices.<ref name="Uckoo" /> |
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Although few oj, double-blind human studies have been done, animal research shows the potential of tangeritin as a cholesterol lowering agent<ref>{{cite journal |author=Kurowska EM, Manthey JA |title=Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia |journal=J. Agric. Food Chem. |volume=52 |issue=10 |pages=2879–86 |year=2004 |month=May |pmid=15137829 |doi=10.1021/jf035354z }}</ref>. A hamster study showed potential protective effects against ]<ref>{{cite journal |author=Datla KP, Christidou M, Widmer WW, Rooprai HK, Dexter DT |title=Tissue distribution and neuroprotective effects of citrus flavonoid tangeretin in a rat model of Parkinson's disease |journal=Neuroreport |volume=12 |issue=17 |pages=3871–5 |year=2001 |month=December |pmid=11726811 |doi=10.1097/00001756-200112040-00053 }}</ref>. Tangeritin shows potential as an anti cancer agent. In in vitro studies, tangeritin appears to counteract some of the adaptations of cancer cells. Tangeritin induced ] in leukemia cells while sparing normal cells<ref>{{cite journal |author=Hirano T, Abe K, Gotoh M, Oka K |title=Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes |journal=Br. J. Cancer |volume=72 |issue=6 |pages=1380–8 |year=1995 |month=December |pmid=8519648 |pmc=2034105 }}</ref>. It counteracts tumor suppression of ] ]<ref>{{cite journal |author=Chaumontet C, Droumaguet C, Bex V, Heberden C, Gaillard-Sanchez I, Martel P |title=Flavonoids (apigenin, tangeretin) counteract tumor promoter-induced inhibition of intercellular communication of rat liver epithelial cells |journal=Cancer Lett. |volume=114 |issue=1-2 |pages=207–10 |year=1997 |month=March |pmid=9103293 |doi=10.1016/S0304-3835(97)04664-8 }}</ref>. It acts to freeze cancer cells in phase ] of the cell cycle, preventing replication. In summary, ''in vitro'' studies show antimutagenic<ref>{{cite journal |author=Calomme M, Pieters L, Vlietinck A, Vanden Berghe D |title=Inhibition of bacterial mutagenesis by Citrus flavonoids |journal=Planta Med. |volume=62 |issue=3 |pages=222–6 |year=1996 |month=June |pmid=8693033 |doi=10.1055/s-2006-957864 }}</ref>, antiinvasive<ref>{{cite journal |author=Bracke ME, Vyncke BM, Van Larebeke NA, ''et al.'' |title=The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro |journal=Clin. Exp. Metastasis |volume=7 |issue=3 |pages=283–300 |year=1989 |pmid=2924447 |doi=10.1007/BF01753681 }}</ref> and antiproliferative<ref>{{cite journal |author=Kandaswami C, Perkins E, Soloniuk DS, Drzewiecki G, Middleton E |title=Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro |journal=Cancer Lett. |volume=56 |issue=2 |pages=147–52 |year=1991 |month=February |pmid=1998943 |doi=10.1016/0304-3835(91)90089-Z }}</ref> effects. One caveat is that tangeritin appears to counteract the anticancer drug ] and to suppress the activity of natural killer cells<ref>{{cite journal |author=Depypere HT, Bracke ME, Boterberg T, ''et al.'' |title=Inhibition of tamoxifen's therapeutic benefit by tangeretin in mammary cancer |journal=Eur. J. Cancer |volume=36 |issue=Suppl 4|pages=S73 |year=2000 |month=September |pmid=11056327 |doi=10.1016/S0959-8049(00)00234-3 }}</ref>. |
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The following is a list of methods used to extract tangeretin from citrus peels: |
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Tangeritin is commercially available as a dietary supplement. |
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* column chromatography |
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* preparative-high performance liquid chromatography |
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* super critical fluid chromatography |
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* high speed counter current chromatography |
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* a combination of vacuum flash silica gel chromatography and flash C<sub>8</sub> column chromatography |
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* flash chromatography |
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* isolation using ionic liquids and a cycle of centrifugation and decantation<ref name = "Mizuno, H. et al.">Mizuno, H.; Yoshikawa, H.; Usuki, T. Extraction of Nobiletin and Tangeretin From Peels of Shekwasha and Ponkan Using and Centrifugation. Natural Product Communications 2019, 14, 1-6. |
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</ref> |
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The low solubility of Tangeretin is one of the main reasons for the low bioavailability of Tangeretin (and other flavonoids in general), and has been reported as a major challenge when using the compound in laboratory procedures.<ref name = "Panche, A. N. et al.">Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47. |
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</ref> |
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However, methods for tangeretin extraction are currently being tested to maximize efficiency and percent yields as its uses in treatment of cancer and other diseases are becoming better understood.<ref name="Uckoo" /> |
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Tangeretin is commercially available as a dietary supplement. Tangeretin has also demonstrated beneficial applications in other pharmaceutical, nutraceutical, and cosmetic processes.<ref name = "Panche, A. N. et al."></ref> |
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==References== |
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Tangeretin can be found as various synonyms throughout literature and research, including '''Tangeritin''' and '''5,6,7,8,4’-pentamethoxyflavone (VIII)'''.<ref name = "Mizuno, H. et al."></ref> |
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== References == |
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