Cas no 61775-19-7 (5-O-Methylnaringenin)

5-O-Methylnaringenin is a flavonoid derivative structurally related to naringenin, featuring a methyl group at the 5-O position. This modification enhances its lipophilicity and metabolic stability compared to its parent compound. It exhibits potential bioactivity as an antioxidant, anti-inflammatory agent, and modulator of enzymatic pathways. The compound is of interest in pharmacological research due to its improved bioavailability and potential therapeutic applications, including cardiovascular and metabolic disorders. Its well-defined chemical structure allows for precise study of structure-activity relationships. 5-O-Methylnaringenin is typically synthesized under controlled conditions to ensure high purity, making it suitable for analytical and experimental use in biochemistry and medicinal chemistry research.
5-O-Methylnaringenin structure
5-O-Methylnaringenin structure
Product Name:5-O-Methylnaringenin
CAS No:61775-19-7
MF:C16H14O5
MW:286.27936
MDL:MFCD20260986
CID:836781
PubChem ID:182315
Update Time:2025-10-13

5-O-Methylnaringenin Chemical and Physical Properties

Names and Identifiers

    • (S)-7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxychroman-4-one
    • 5-O-Methylnaringenin
    • (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydrochromen-4-one
    • (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-chroman-4-one
    • 7,4'-Dihydroxy-5-methoxyflavanone
    • (-)-7,4'-Dihydroxy-5-methoxyflavanone
    • Naringenin 5-methyl ether
    • Naringenin 5-O-methyl ether
    • DTXSID90977353
    • 7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
    • HY-N2683
    • 61775-19-7
    • 5-O-Methylnaringenin; 7,4'-Dihydroxy-5-methoxyflavanone; Naringenin 5-methyl ether
    • CHEMBL255035
    • 5-O-Methylnaringenin, >=95% (LC/MS-ELSD)
    • Naringenin 5-Me4thyl ether
    • FS-8884
    • 5-Methoxynaringenin
    • AKOS022184567
    • CS-0023123
    • SCHEMBL799649
    • [ "" ]
    • DB-333126
    • (2S)-7-HYDROXY-2-(4-HYDROXYPHENYL)-5-METHOXY-2,3-DIHYDRO-1-BENZOPYRAN-4-ONE
    • MDL: MFCD20260986
    • Inchi: InChI=1S/C16H14O5/c1-20-14-6-11(18)7-15-16(14)12(19)8-13(21-15)9-2-4-10(17)5-3-9/h2-7,13,17-18H,8H2,1H3
    • InChI Key: CWZLMWSCLBFCBY-UHFFFAOYSA-N
    • SMILES: COC1=CC(=CC2=C1C(=O)CC(O2)C3=CC=C(C=C3)O)O

Computed Properties

  • Exact Mass: 286.08400
  • Monoisotopic Mass: 286.084124
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 2
  • Complexity: 377
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 76
  • XLogP3: 2.2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.37
  • Boiling Point: 555.9°C at 760 mmHg
  • Flash Point: 212.4°C
  • Refractive Index: 1.637
  • PSA: 75.99000
  • LogP: 2.81290

5-O-Methylnaringenin Security Information

  • Hazardous Material transportation number:UN 3077 9 / PGIII
  • Hazard Category Code: 50
  • Safety Instruction: 61
  • Hazardous Material Identification: N
  • Storage Condition:?20°C

5-O-Methylnaringenin Customs Data

  • HS CODE:2932999099
  • Customs Data:

    China Customs Code:

    2932999099

    Overview:

    2932999099. Other heterocyclic compounds containing only oxygen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

5-O-Methylnaringenin Pricemore >>

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Additional information on 5-O-Methylnaringenin

5-O-Methylnaringenin (CAS No. 61775-19-7): An Overview of Its Properties, Applications, and Recent Research

5-O-Methylnaringenin (CAS No. 61775-19-7) is a naturally occurring flavonoid that has garnered significant attention in the fields of chemistry, biology, and pharmacology due to its diverse biological activities and potential therapeutic applications. This compound is primarily found in various plants, including citrus fruits, where it contributes to their characteristic health benefits.

The chemical structure of 5-O-Methylnaringenin is characterized by a flavanone skeleton with a methoxy group at the 5-position. This unique structural feature imparts distinct properties that differentiate it from other flavonoids. The compound's molecular formula is C16H14O6, and its molecular weight is 302.28 g/mol. The presence of multiple hydroxyl and methoxy groups makes it highly polar and soluble in water, which facilitates its absorption and bioavailability in biological systems.

Recent research has highlighted the multifaceted biological activities of 5-O-Methylnaringenin. One of the most notable properties is its potent antioxidant activity. Studies have shown that 5-O-Methylnaringenin can effectively scavenge free radicals and inhibit lipid peroxidation, thereby protecting cells from oxidative stress-induced damage. This property makes it a promising candidate for the prevention and treatment of various oxidative stress-related diseases, such as cardiovascular diseases, neurodegenerative disorders, and cancer.

In addition to its antioxidant effects, 5-O-Methylnaringenin exhibits anti-inflammatory properties. In vitro and in vivo studies have demonstrated that it can modulate the expression of pro-inflammatory cytokines and enzymes, such as tumor necrosis factor-alpha (TNF-α) and cyclooxygenase-2 (COX-2). These findings suggest that 5-O-Methylnaringenin could be beneficial in managing inflammatory conditions like arthritis and inflammatory bowel disease.

The anti-cancer potential of 5-O-Methylnaringenin has also been extensively investigated. Research has shown that it can induce apoptosis in various cancer cell lines, including breast cancer, colon cancer, and liver cancer cells. The mechanism of action involves the modulation of multiple signaling pathways, such as the PI3K/Akt pathway and the MAPK pathway. Furthermore, 5-O-Methylnaringenin has been found to enhance the efficacy of conventional chemotherapeutic agents by sensitizing cancer cells to drug-induced apoptosis.

Beyond its direct biological activities, 5-O-Methylnaringenin has been explored for its potential as a natural preservative in food and cosmetic products. Its antimicrobial properties have been demonstrated against various pathogenic bacteria and fungi, making it a viable alternative to synthetic preservatives. Additionally, its ability to stabilize lipid-based formulations due to its antioxidant properties adds value to its application in the food and cosmetic industries.

In the realm of drug development, 5-O-Methylnaringenin has shown promise as a lead compound for the synthesis of novel pharmaceuticals. Researchers are actively investigating structural modifications to enhance its bioavailability, stability, and therapeutic efficacy. For instance, conjugation with other bioactive molecules or encapsulation in nanocarriers can improve its pharmacokinetic profile and target delivery to specific tissues or organs.

The safety profile of 5-O-Methylnaringenin is another critical aspect that has been evaluated in preclinical studies. Toxicity assessments have indicated that it is well-tolerated at therapeutic concentrations with minimal adverse effects. However, further clinical trials are necessary to confirm its safety and efficacy in human subjects.

In conclusion, 5-O-Methylnaringenin (CAS No. 61775-19-7) is a versatile flavonoid with a wide range of biological activities and potential applications in medicine, food science, and cosmetics. Ongoing research continues to uncover new insights into its mechanisms of action and therapeutic potential, positioning it as a valuable natural compound for future development.

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