Tangeretin - Moligand™, ≥95% , CAS No.481-53-8

CAS: 481-53-8 Cat. No.: T123655 Molecular Weight: 372.37 Beilstein Registry Number: 351695 EC Number: 207-570-1 PubChem CID: 68077

GRADE & PURITY Moligand™, ≥95%

Synonyms

NSC 618905 | Tangeritin | Pentamethoxyflavone | NSC 53909 | 4',5,6,7,8-Pentamethoxyflavone | 5,6,7,8,4'-Pentamethoxyflavone | Ponkanetin | 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Tangeretin is a flavonoid found in the peel of citrus fruits where it most likely provides natural resistance to fungi. Tangeretin has been shown to counteract tumor promoter-induced inhibition of intercellular communication and to inhibit cell proliferation in several cancer lines

Specifications

Synonyms

NSC 618905 | Tangeritin | Pentamethoxyflavone | NSC 53909 | 4', 5, 6, 7, 8-Pentamethoxyflavone | 5, 6, 7, 8, 4'-Pentamethoxyflavone | Ponkanetin | 5, 6, 7, 8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Tangeretin is a flavonoid found in the peel of citrus fruits where it most likely provides natural resistance to fungi. Tangeretin has been shown to counteract tumor promoter-induced inhibition of intercellular communication. and to inhibit cell prolifera

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504754246
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754246
• Canonical Smiles: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC
• IUPAC Name: 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
• InChIKey: ULSUXBXHSYSGDT-UHFFFAOYSA-N
• 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
• Isomeric SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC
• WGK Germany: 3
• RTECS: DJ3102725
• PubChem CID: 68077
• Molecular Weight: 372.37
• Beilstein: 351695
• Reaxy-Rn: 351695

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass O-methylated flavonoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: O-methylated flavonoids
• Intermediate Tree Nodes: Not available
• Direct Parent: 8-O-methylated flavonoids
• Alternative Parents: 4'-O-methylated flavonoids 5-O-methylated flavonoids 6-O-methylated flavonoids 7-O-methylated flavonoids Flavones Chromones Phenoxy compounds Methoxybenzenes Anisoles Pyranones and derivatives Alkyl aryl ethers Vinylogous esters Heteroaromatic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: Flavones and Flavonols

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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P2RY2 Tclin Purinergic receptor P2Y2 (1109 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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LoVo (4724 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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Panel NCI-60 (60 carcinoma cell lines) (1088 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SH-SY5Y (11521 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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HOP-92 (41141 Activities)

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Hs-578T (29457 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Salmonella typhimurium (15756 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Penicillium digitatum (260 Activities)

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3T3-L1 (3664 Activities)

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CCRF S-180 (1031 Activities)

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L1210 (27553 Activities)

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RBL-2H3 (1162 Activities)

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norA Quinolone resistance protein norA (2171 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Phytophthora citrophthora (55 Activities)

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Spodoptera litura (1708 Activities)

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Citrus (8 Activities)

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mdeA Fluoroquinolone resistance protein (28 Activities)

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ureB Urease subunit alpha/Urease subunit beta (701 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat Sensitive
• Melt Point(°C): 153.0-157.0°C
• Molecular Weight: 372.400 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 372.121 Da
• Monoisotopic Mass: 372.121 Da
• Topological Polar Surface Area: 72.500 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 540.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tingyan Liu, Caiyan Zhang, Jiayun Ying, Yaodong Wang, Gangfeng Yan, Yufeng Zhou, Guoping Lu.  (2023)  Inhibition of the intracellular domain of Notch1 results in vascular endothelial cell dysfunction in sepsis.  Frontiers in Immunology,      [PMID:37205094] [10.3389/fimmu.2023.1134556]

2. Yajing Fang, Fuqiang Liang, Mengmeng Xia, Weiwei Cao, Siyi Pan, Ting Wu, Xiaoyun Xu.  (2021)  Structure-activity relationship and mechanism of flavonoids on the inhibitory activity of P-glycoprotein (P-gp)-mediated transport of rhodamine123 and daunorubicin in P-gp overexpressed human mouth epidermal carcinoma (KB/MDR) cells.  FOOD AND CHEMICAL TOXICOLOGY,      [PMID:34217736] [10.1016/j.fct.2021.112381]

3. Xin Huang, Junxiang Zhu, Li Wang, Huijuan Jing, Chaoyang Ma, Xingran Kou, Hongxin Wang.  (2020)  Inhibitory mechanisms and interaction of tangeretin, 5-demethyltangeretin, nobiletin, and 5-demethylnobiletin from citrus peels on pancreatic lipase: Kinetics, spectroscopies, and molecular dynamics simulation.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:32795575] [10.1016/j.ijbiomac.2020.07.305]

4. Yao Hu, Yang Qin, Chao Qiu, Xueming Xu, Zhengyu Jin, Jinpeng Wang.  (2020)  Ultrasound-assisted self-assembly of β-cyclodextrin/debranched starch nanoparticles as promising carriers of tangeretin.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2020.106021]

5. Xin Huang, Xingran Kou, Li Wang, Ruya Ji, Chaoyang Ma, Hongxin Wang.  (2019)  Effective hydroxylation of tangeretin from Citrus Peel (Chenpi) by edible acids and its improvement in antioxidant and anti-lipase activities.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2019.108469]

6. Fuqiang Liang, Yajing Fang, Weiwei Cao, Zhuo Zhang, Siyi Pan, Xiaoyun Xu.  (2018)  Attenuation of tert-Butyl Hydroperoxide (t-BHP)-Induced Oxidative Damage in HepG2 Cells by Tangeretin: Relevance of the Nrf2–ARE and MAPK Signaling Pathways.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:29871486] [10.1021/acs.jafc.8b01875]

7. Kai Ni, Bo Che, Rong Gu, Chunhong Wang, Hongyang Xu, Huiduo Li, Shiyan Cen, Mingzhi Luo, Linhong Deng.  (2024)  BitterDB database analysis plus cell stiffness screening identify flufenamic acid as the most potent TAS2R14-based relaxant of airway smooth muscle cells for therapeutic bronchodilation.  Theranostics,      [PMID:38389834] [10.7150/thno.92492]

8. Yating Lu, Dong Li, Li Li, Tarun Belwal, Yanqun Xu, Xingyu Lin, Zhenhua Duan, Zisheng Luo.  (2020)  Effects of elevated CO2 on pigment metabolism of postharvest mandarin fruit for degreening.  FOOD CHEMISTRY,      [PMID:32126463] [10.1016/j.foodchem.2020.126462]