Cas no 6754-58-1 (Xanthohumol)

Xanthohumol is a prenylated flavonoid primarily found in hops (Humulus lupulus). It exhibits notable biological activities, including antioxidant, anti-inflammatory, and potential chemopreventive properties. Research suggests it may modulate cellular pathways involved in oxidative stress and inflammation, making it of interest for nutraceutical and pharmaceutical applications. Xanthohumol is also studied for its potential role in metabolic health, including lipid metabolism and glucose regulation. Its stability and bioavailability are areas of ongoing investigation, with efforts focused on optimizing extraction and formulation techniques. As a naturally derived compound, it aligns with growing demand for plant-based bioactive ingredients in health-focused industries.
Xanthohumol structure
Xanthohumol structure
Product Name:Xanthohumol
CAS No:6754-58-1
MF:C21H5O5
MW:337.261405706406
MDL:MFCD00210576
CID:512378
PubChem ID:253659967
Update Time:2025-05-21

Xanthohumol Chemical and Physical Properties

Names and Identifiers

    • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • Xanthohumo
    • (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • 2-Propen-1-one,1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)-
    • 2-Propen-1-one,1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)...
    • XANTHOHUMOL(RG)
    • Xanthohumol
    • XANTHOHUMOL(P)
    • (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone
    • 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone
    • (2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
    • [ "2'", "4", "4'-Trihydroxy-6'-methoxy-3'-prenylchalcone" ]
    • 2'
    • T4467YT1NT
    • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
    • (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • (E)-1
    • MDL: MFCD00210576
    • Inchi: 1S/C21H5O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h5-6,8-9,12H
    • InChI Key: QMTRRSDEVOXVDU-UHFFFAOYSA-N
    • SMILES: [C]OC1C(C(/[C]=[C]/C2C=CC([O])=CC=2)=O)=C([O])C([C]/[C]=C(\[C])/[C])=C([O])C=1 |^1:0,5,6,11,16,19,21,22,24,^4:18|

Computed Properties

  • Exact Mass: 354.14700
  • Monoisotopic Mass: 354.14672380 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 6
  • Complexity: 515
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 87
  • Surface Charge: 0
  • Tautomer Count: 57
  • XLogP3: 5.1
  • Molecular Weight: 354.4

Experimental Properties

  • Color/Form: Orange powder
  • Density: 1.244
  • Melting Point: 158.0 to 163.0 deg-C
  • Boiling Point: 576.00to577.00°[email protected](est)
  • Solubility: ethanol: soluble10mg/mL
  • PSA: 86.99000
  • LogP: 4.21680

Xanthohumol Security Information

  • Symbol: GHS07 GHS09
  • Signal Word:Warning
  • Hazard Statement: H317-H400
  • Warning Statement: P273-P280
  • Hazardous Material transportation number:UN 3077 9
  • WGK Germany:3
  • Hazard Category Code: 43-50/53
  • Safety Instruction: 60-61
  • RTECS:UD5574117
  • Hazardous Material Identification: N
  • Risk Phrases:R50/53
  • Storage Condition:0-10°C

Xanthohumol Pricemore >>

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Additional information on Xanthohumol

Xanthohumol: A Comprehensive Overview

Xanthohumol, also known by its CAS number 6754-58-1, is a bioactive compound that has garnered significant attention in recent years due to its diverse pharmacological properties. This compound, primarily found in hops (Humulus lupulus), belongs to the class of prenylated flavonoids and exhibits a unique chemical structure that contributes to its potent biological activities. Recent studies have highlighted its potential in various therapeutic applications, making it a subject of extensive research in the fields of pharmacology, nutrition, and natural product chemistry.

The chemical structure of Xanthohumol is characterized by a flavonoid backbone with a prenyl group attached, which plays a crucial role in its bioavailability and activity. This structure allows Xanthohumol to interact with multiple cellular pathways, including those involved in inflammation, oxidative stress, and cancer progression. Recent advancements in analytical techniques have enabled researchers to better understand the stereochemistry and biosynthesis of Xanthohumol, paving the way for its potential use in drug development.

One of the most promising areas of research involving Xanthohumol is its anti-inflammatory properties. Studies have demonstrated that Xanthohumol can inhibit key inflammatory mediators such as cyclooxygenase-2 (COX-2) and nuclear factor-kappa B (NF-κB). These findings suggest that Xanthohumol could be a potential candidate for treating inflammatory diseases such as arthritis, inflammatory bowel disease, and neuroinflammation. Moreover, its ability to modulate these pathways without causing significant side effects makes it an attractive alternative to conventional anti-inflammatory drugs.

Another area where Xanthohumol has shown remarkable potential is in cancer prevention and treatment. Research indicates that Xanthohumol can induce apoptosis in various cancer cell lines while sparing normal cells. This selective cytotoxicity is attributed to its ability to target specific oncogenic pathways, such as the PI3K/AKT/mTOR pathway. Additionally, Xanthohumol has been found to enhance the efficacy of chemotherapy drugs and reduce their associated side effects, making it a potential adjuvant in cancer therapy.

The antioxidant properties of Xanthohumol are another key area of interest. By neutralizing reactive oxygen species (ROS) and enhancing the activity of endogenous antioxidant enzymes like glutathione peroxidase, Xanthohumol helps protect cells from oxidative damage. This property is particularly relevant in the context of age-related diseases such as Alzheimer's disease and cardiovascular disorders. Recent studies have also explored the role of Xanthohumol in mitigating oxidative stress-induced damage in neuronal cells, highlighting its potential as a neuroprotective agent.

In addition to its therapeutic applications, Xanthohumol has gained recognition in the food and beverage industry as a natural ingredient with health-promoting benefits. Its presence in hops makes it a common constituent of beer, where it contributes not only to the flavor profile but also offers potential health benefits to consumers. The food industry is increasingly exploring ways to incorporate Xanthohumol into functional foods and beverages to capitalize on its antioxidant and anti-inflammatory properties.

Recent advancements in biotechnology have also led to innovative methods for producing Xanthohumol on an industrial scale. Techniques such as metabolic engineering and fermentation optimization are being employed to enhance the yield of this compound from microbial sources. These developments are expected to make Xanthohumol more accessible for both research and commercial applications.

In conclusion, Xanthohumol (CAS 6754-58-1) is a multifaceted compound with a wide range of biological activities that make it a valuable asset in various fields. From its anti-inflammatory and anticancer properties to its role as a natural ingredient in food products, ongoing research continues to uncover new potentials for this remarkable compound. As scientific understanding of Xanthohumol deepens, it holds promise for becoming an integral part of future therapeutic strategies and functional food formulations.

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