Hispidulin - ≥98%(HPLC) , CAS No.1447-88-7

CAS: 1447-88-7 Cat. No.: H167320 Molecular Weight: 300.26 EC Number: 802-856-8

GRADE & PURITY ≥98%(HPLC)

Synonyms

methoxyapigenin | SMR000445653 | BRD-K72066874-001-01-0 | TCMDC-123942 | Flavone,5,7-trihydroxy-6-methoxy- | UNII-N7F61604C2 | PubChem SID: 26725244 | CCRIS 8484 | FT-0697687 | SCHEMBL514926 | 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-6-methoxy-chromen-4-one | 5

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Hispidulin has been used as a calibration standard: in high-performance liquid chromatography (HPLC) for quantification of Clerodendrum petasites flavonoids in liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) analysis in reverse-phase high-performance liquid chromatography with a diode-array detector (HPLC-DAD) and high-performance thin-layer chromatography (HPTLC)

Specifications

Synonyms

methoxyapigenin | SMR000445653 | BRD-K72066874-001-01-0 | TCMDC-123942 | Flavone, 5, 7-trihydroxy-6-methoxy- | UNII-N7F61604C2 | PubChem SID: 26725244 | CCRIS 8484 | FT-0697687 | SCHEMBL514926 | 5, 7-Dihydroxy-2-(4-hydroxy-phenyl)-6-methoxy-chromen-4-one | 5

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Partial positive allosteric modulator at the benzodiazepine receptor (IC50= 1.3μM for inhibition of flumazenil binding); natural sage flavone. Stimulates GABA-induced chloride currents in Xenopus oocytes expressingα1-, α2-, α3-, α5- orα6-β2γ2S GABAAreceptors

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504763369
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763369
• Canonical Smiles: COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxychromen-4-one
• InChIKey: IHFBPDAQLQOCBX-UHFFFAOYSA-N
• INCHI: 1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
• Isomeric SMILES: COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
• WGK Germany: 3
• RTECS: DJ2996000
• Molecular Weight: 300.26
• Reaxy-Rn: 1293933
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1293933&ln=

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: 6-O-methylated flavonoids
• Alternative Parents: 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Chromones Anisoles 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Vinylogous acids Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 6-methoxyflavonoid-skeleton - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Anisole - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Pyranone - Phenol - Monocyclic benzene moiety - Benzenoid - Pyran - Vinylogous acid - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Ether - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 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)

GFER Tchem FAD-linked sulfhydryl oxidase ALR (1 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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FLT3 Tclin Tyrosine-protein kinase receptor FLT3 (13481 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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ATM Tchem Serine-protein kinase ATM (4198 Activities)

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MKNK2 Tchem MAP kinase signal-integrating kinase 2 (3518 Activities)

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A498 (42825 Activities)

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ACHN (49357 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-1080 (3966 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 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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PC-3 (62116 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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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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ZR-75-1 (953 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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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

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DPP4 Dipeptidyl peptidase IV (11 Activities)

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Proteus vulgaris (5823 Activities)

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Bacillus subtilis (32866 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Plasmodium falciparum (966862 Activities)

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Hepatitis C virus (23859 Activities)

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Influenza A virus (11224 Activities)

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MDCK (10148 Activities)

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P388 (20296 Activities)

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ht1 Hexose transporter 1 (14071 Activities)

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Avian myoblastosis virus polyprotein II (68 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Cdk5 Cell division protein kinase 5 (15 Activities)

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Plasma (328 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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Gabrp GABA-A receptor; anion channel (5731 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 7.51, Max Conc. mM: 25; Solvent:ethanol, Max Conc. mg/mL: 3, Max Conc. mM: 10
• Molecular Weight: 300.260 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 300.063 Da
• Monoisotopic Mass: 300.063 Da
• Topological Polar Surface Area: 96.200 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 454.000
• 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. Zhihua Chen, Guofeng Zhu, Chunpeng Sheng, Jianwei Lei, Sihui Song, Jianming Zhu.  (2022)  Hispidulin Enhances Temozolomide (TMZ)-Induced Cytotoxicity against Malignant Glioma Cells In Vitro by Inhibiting Autophagy.  Computational Intelligence and Neuroscience,      [PMID:35800695] [10.1155/2022/5266770]

2. Xiaoli Wang, Jichen Yang, Huan Li, Se Shi, Xin Peng.  (2022)  Mechanistic study and synergistic effect on inhibition of α-amylase by structurally similar flavonoids.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2022.119485]

3. Li Lv, Wenhui Zhang, Tingting Li, Lifeng Jiang, Xinyan Lu, Jie Lin.  (2020)  Hispidulin exhibits potent anticancer activity in vitro and in vivo through activating ER stress in non‑small‑cell lung cancer cells.  ONCOLOGY REPORTS,  43  (6): (1995-2003).  [PMID:32236602] [10.3892/or.2020.7568]

4. Dapeng Chen, Jiayi Li, Xinyu Li, Kexin Zhang, Shujie Zeng, Shenjun Zhang, Longyun Li, Yongjian Xiong.  (2025)  Dietary hispidulin ameliorated chemically-Induced colitis by inhibiting epithelial cell ferroptosis via the ACAT2-GPX4 axis and remodeling the gut microbiota.  Food & Function,      [PMID:40856206] [10.1039/D5FO02648B]