Cas no 4143-74-2 (4'-Methoxyflavone)

4'-Methoxyflavone is a synthetic flavonoid derivative characterized by the presence of a methoxy group at the 4' position of the flavone backbone. This modification enhances its stability and alters its physicochemical properties, making it a valuable intermediate in organic synthesis and pharmaceutical research. The compound exhibits potential bioactivity due to its structural similarity to naturally occurring flavonoids, which are known for their antioxidant and anti-inflammatory properties. Its well-defined structure and high purity make it suitable for mechanistic studies and drug development. 4'-Methoxyflavone is commonly used in research applications, particularly in the investigation of flavonoid-related biochemical pathways and receptor interactions.
4'-Methoxyflavone structure
4'-Methoxyflavone structure
Product Name:4'-Methoxyflavone
CAS No:4143-74-2
MF:C16H12O3
MW:252.264684677124
MDL:MFCD00016934
CID:331350
PubChem ID:77793
Update Time:2025-05-24

4'-Methoxyflavone Chemical and Physical Properties

Names and Identifiers

    • 4H-1-Benzopyran-4-one,2-(4-methoxyphenyl)-
    • 4'-Methoxyflavone
    • 2-(4-methoxyphenyl)chromen-4-one
    • METHOXYFLAVONE, 4'-(RG)
    • 4' methoxyflavone
    • 2-(4-Methoxyphenyl)-4H-chromen-4-one
    • 2-(4-Methoxyphenyl)chromone
    • 4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-
    • 4-Methoxy Flavone
    • 2-(4-Methoxy-phenyl)-chromen-4-one
    • 2-(4-Methoxyphenyl)-4-benzopyrone
    • OMICQBVLCVRFGN-UHFFFAOYSA-N
    • 2-(4-methoxyphenyl)-1-benzopyran-4-one
    • 4''-methoxyflavone
    • Flavone, 4'-methoxy
    • Spectrum_000114
    • 2-(4-methoxyphenyl)-4h-benzopyran-4-one
    • Spectrum5_000417
    • Spectrum3_001269
    • Sp
    • A63
    • KBio2_000554
    • NCGC00095556-03
    • SDCCGMLS-0066544.P001
    • HMS2271I03
    • AKOS000603631
    • CBiol_000291
    • PD002073
    • ACon1_002036
    • BRD-K76337122-001-03-7
    • 4143-74-2
    • SMR000440756
    • BIDD:ER0472
    • BRD-K76337122-001-02-9
    • AS-56897
    • AD-310/30361023
    • KBioGR_002037
    • DTXSID0063319
    • KBio2_005690
    • cid_77793
    • SPBio_000848
    • Spectrum2_000774
    • Q27195318
    • NS00015829
    • NCGC00095556-01
    • BSPBio_002838
    • 2-(4-methoxy-phenyl)-4H-chromen-4-one
    • EINECS 223-968-8
    • CHEMBL16312
    • Oprea1_274709
    • CHEBI:114194
    • SCHEMBL311931
    • MEGxp0_001873
    • NCGC00178443-01
    • SR-01000471678-3
    • FT-0733585
    • SR-01000471678-1
    • Cambridge id 5324654
    • Oprea1_031095
    • ICCB2_000291
    • 4l10
    • KBio3_002338
    • KBioSS_000554
    • BIM-0029447.P001
    • CCG-40164
    • Spectrum4_001629
    • MLS000863607
    • ChemDiv2_004185
    • HMS1380O05
    • SR-01000471678
    • BDBM50310189
    • 2-(4-methoxyphenyl)-chromen-4-one
    • M2887
    • IDI1_002900
    • CBMicro_029575
    • MFCD00016934
    • KBio2_003122
    • NCGC00095556-02
    • SPECTRUM240958
    • T72446
    • NCGC00178443-02
    • EU-0042497
    • F0400-0028
    • MLSMR
    • HY-139054
    • CS-0179255
    • Flavone, 4'-methoxy-
    • DB-116308
    • MDL: MFCD00016934
    • Inchi: 1S/C16H12O3/c1-18-12-8-6-11(7-9-12)16-10-14(17)13-4-2-3-5-15(13)19-16/h2-10H,1H3
    • InChI Key: OMICQBVLCVRFGN-UHFFFAOYSA-N
    • SMILES: O1C2C=CC=CC=2C(C=C1C1C=CC(=CC=1)OC)=O

Computed Properties

  • Exact Mass: 252.07900
  • Monoisotopic Mass: 252.079
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 2
  • Complexity: 366
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.5
  • Topological Polar Surface Area: 35.5

Experimental Properties

  • Density: 1.24
  • Melting Point: 157.0 to 161.0 deg-C
  • Boiling Point: 401.5 °C at 760 mmHg
  • Flash Point: 188.2 °C
  • Refractive Index: 1.614
  • Solubility: DMSO: soluble5mg/mL, clear (warmed)
  • PSA: 39.44000
  • LogP: 3.46860
  • λmax: 319(MeOH)(lit.)

4'-Methoxyflavone Security Information

4'-Methoxyflavone Customs Data

  • HS CODE:2914509090
  • Customs Data:

    China Customs Code:

    2914509090

    Overview:

    2914509090 Ketones containing other oxygen-containing groups. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, Acetone declared packaging

    Summary:

    HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

4'-Methoxyflavone Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.
M869911-200mg
4'-Methoxyflavone
4143-74-2 98%
200mg
644.40 2021-05-17
TRC
M268565-2.5mg
4'-Methoxyflavone
4143-74-2
2.5mg
$ 50.00 2022-06-04
TRC
M268565-5mg
4'-Methoxyflavone
4143-74-2
5mg
$ 70.00 2022-06-04
TRC
M268565-25mg
4'-Methoxyflavone
4143-74-2
25mg
$ 275.00 2022-06-04
SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd.
M41180-20mg
2-(4-methoxyphenyl)chromen-4-one
4143-74-2
20mg
¥668.0 2022-04-27
Chemenu
CM300344-50mg
2-(4-Methoxyphenyl)-4H-chromen-4-one
4143-74-2 97%
50mg
$281 2021-06-17
SHANG HAI XIAN DING Biotechnology Co., Ltd.
M2887-1g
4'-Methoxyflavone
4143-74-2 98.0%(GC)
1g
¥990.0 2022-07-29
TI XI AI ( SHANG HAI ) HUA CHENG GONG YE FA ZHAN Co., Ltd.
M2887-1G
4'-Methoxyflavone
4143-74-2 >98.0%(GC)
1g
¥690.00 2024-04-16
SHANG HAI XIAN DING Biotechnology Co., Ltd.
PX682-200mg
4'-Methoxyflavone
4143-74-2 98.0%(GC)
200mg
¥900.0 2022-02-28
Chemenu
CM300344-50mg
2-(4-Methoxyphenyl)-4H-chromen-4-one
4143-74-2 97%
50mg
$*** 2023-03-30

4'-Methoxyflavone Related Literature

Additional information on 4'-Methoxyflavone

Chemical Profile and Research Applications of 4'-Methoxyflavone (CAS No. 4143-74-2)

4'-Methoxyflavone, chemically known by the CAS number 4143-74-2, is a flavonoid derivative that has garnered significant attention in the field of pharmaceutical and biochemical research. Flavonoids are a class of natural polyphenolic compounds widely distributed in plants, and they are known for their diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties. The methoxylation at the 4'-position of the flavone scaffold in 4'-Methoxyflavone contributes to its unique pharmacological profile, making it a subject of extensive investigation for potential therapeutic applications.

The chemical structure of 4'-Methoxyflavone consists of a benzopyran nucleus with a methoxy group at the 4'-position and hydroxyl groups at the 5- and 7-positions. This structural configuration imparts distinct electronic and steric properties, influencing its interactions with biological targets. The compound exhibits moderate solubility in organic solvents but limited solubility in water, which poses challenges for formulation development but also suggests potential for targeted delivery systems.

Recent research has highlighted the pharmacological potential of 4'-Methoxyflavone in several therapeutic areas. One of the most promising applications is in oncology. Studies have demonstrated that 4'-Methoxyflavone can modulate key signaling pathways involved in cancer cell proliferation and survival. For instance, it has been shown to inhibit the activity of the epidermal growth factor receptor (EGFR), a critical driver in many cancers, by competing with its natural ligands for receptor binding. Additionally, 4'-Methoxyflavone has been reported to induce apoptosis in various cancer cell lines by activating caspase-dependent pathways, suggesting its potential as an adjuvant therapy alongside conventional chemotherapeutic agents.

In addition to its anti-cancer properties, 4'-Methoxyflavone has shown significant promise in neuroprotective research. Oxidative stress and inflammation are key pathological features of neurodegenerative diseases such as Alzheimer's and Parkinson's disease. Preclinical studies indicate that 4'-Methoxyflavone can mitigate oxidative damage by scavenging reactive oxygen species (ROS) and inhibiting inflammatory enzymes like nitric oxide synthase (NOS) and cyclooxygenase (COX). Furthermore, its ability to cross the blood-brain barrier enhances its therapeutic relevance for central nervous system disorders.

The anti-inflammatory effects of 4'-Methoxyflavone have also been explored in conditions characterized by chronic inflammation, such as rheumatoid arthritis and inflammatory bowel disease. By inhibiting key pro-inflammatory cytokines like tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6), 4'-Methoxyflavone demonstrates potential as a natural anti-inflammatory agent. Its mechanism involves modulation of nuclear factor kappa B (NF-κB) signaling, a central regulator of inflammatory responses.

Beyond its therapeutic applications, 4'-Methoxyflavone has been investigated for its metabolic benefits. Research suggests that it can enhance insulin sensitivity by improving glucose uptake in adipose tissues and muscle cells. This effect is attributed to its ability to activate AMP-activated protein kinase (AMPK), an enzyme involved in energy homeostasis. Consequently, 4'-Methoxyflavone is being considered as a candidate compound for managing metabolic syndrome and type 2 diabetes.

The biosynthetic pathway leading to 4'-Methoxyflavone involves the methylation of flavone precursors by methyltransferases. This enzymatic process is influenced by genetic factors and environmental conditions, which can affect the yield and availability of 4'-Methoxyflavone in plant sources. Advances in metabolic engineering have enabled the production of this compound through microbial fermentation using engineered strains of *Escherichia coli* or *Saccharomyces cerevisiae*. Such biotechnological approaches offer scalable solutions for obtaining high-purity 4'-Methoxyflavone, reducing reliance on plant extraction.

In terms of formulation development, researchers have explored various delivery systems to enhance the bioavailability and targeted action of 4'-Methoxyflavone. Liposomal encapsulation has been particularly effective in improving solubility and protecting the compound from rapid degradation. Nanoparticle-based delivery systems have also shown promise for controlled release profiles, allowing sustained therapeutic effects with reduced side effects.

The safety profile of 4'-Methoxyflavone remains a critical area of investigation. While preclinical studies suggest low toxicity at therapeutic doses, long-term human data are limited. Chronic exposure studies are necessary to assess potential off-target effects or cumulative toxicity associated with prolonged use. Pharmacokinetic studies indicate that 4'-Methoxyflavone undergoes extensive metabolism via cytochrome P450 enzymes, particularly CYP3A4 and CYP2C9, which may influence its clinical efficacy and potential drug-drug interactions.

Future research directions include exploring synergistic combinations of 4'-Methoxyflavone with other bioactive compounds or conventional therapeutics to enhance therapeutic outcomes. Additionally, investigating the structure-activity relationships within flavonoid derivatives will aid in designing next-generation analogs with improved pharmacological profiles.

In conclusion, 4’-methoxyflavonewas demonstratedto be a versatile pharmacophore with broad therapeutic potential across multiple disease indications。 Its unique structural features contribute to its diverse biological activities, making it an attractive candidate for further clinical development。 As research continues, additional insights into its mechanisms of actionand optimal delivery strategies will solidifyits role as an important natural product derivativein modern medicine。

Recommended suppliers
Suzhou Senfeida Chemical Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Suzhou Senfeida Chemical Co., Ltd
Xiamen PinR Bio-tech Co., Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Xiamen PinR Bio-tech Co., Ltd.
Zhangzhou Sinobioway Peptide Co.,Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Zhangzhou Sinobioway Peptide Co.,Ltd.
Shandong Feiyang Chemical Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Shandong Feiyang Chemical Co., Ltd
Jiangsu Xinsu New Materials Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Jiangsu Xinsu New Materials Co., Ltd