Cas no 142796-24-5 (2,3-dehydrosilybin)

2,3-Dehydrosilybin is a flavonolignan derivative and an oxidative metabolite of silybin, a primary active constituent of silymarin. This compound exhibits enhanced biological activity compared to its parent molecule, particularly in its antioxidant and hepatoprotective properties. Its conjugated double bond at the 2,3-position increases reactivity, improving free radical scavenging efficiency and potential therapeutic effects. Studies suggest 2,3-dehydrosilybin demonstrates superior inhibitory effects on lipid peroxidation and cytochrome P450 enzymes, making it a promising candidate for research in liver protection and chemoprevention. Its structural modifications also contribute to altered pharmacokinetics, potentially enhancing bioavailability and metabolic stability in pharmacological applications.
2,3-dehydrosilybin structure
2,3-dehydrosilybin structure
Product Name:2,3-dehydrosilybin
CAS No:142796-24-5
MF:C25H20O10
MW:480.420308113098
CID:2077821
PubChem ID:12051803
Update Time:2025-06-15

2,3-dehydrosilybin Chemical and Physical Properties

Names and Identifiers

    • 2,3-dehydrosilybin
    • 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-chromen-4-one
    • dehydrosilybin
    • 2,3-DEHYDROSILYBIN B
    • 2,3-Dehydrosilymarin
    • DA-60017
    • 142796-24-5
    • DTXSID601102493
    • AKOS040735842
    • CS-0899003
    • 2,3-Dehydrosilybin B
    • HY-N12360A
    • 2-[(2S,3S)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
    • 2-((2S,3S)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
    • SFA79624
    • Inchi: 1S/C25H20O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,24,26-29,31H,10H2,1H3/t20-,24-/m0/s1
    • InChI Key: BVKQRAYKLBRNIK-RDPSFJRHSA-N
    • SMILES: O1C2C=C(C3=C(C(C4C(=CC(=CC=4O3)O)O)=O)O)C=CC=2O[C@@H](CO)[C@@H]1C1C=CC(=C(C=1)OC)O

Computed Properties

  • Exact Mass: 480.10564683g/mol
  • Monoisotopic Mass: 480.10564683g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 35
  • Rotatable Bond Count: 4
  • Complexity: 816
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.618
  • Topological Polar Surface Area: 155?2

2,3-dehydrosilybin Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
XI GE MA AO DE LI QI ( SHANG HAI ) MAO YI Co., Ltd.
PHL82878-5MG
2,3-Dehydrosilybin B
142796-24-5
5mg
¥5261.61 2024-12-26
XI GE MA AO DE LI QI ( SHANG HAI ) MAO YI Co., Ltd.
PHL82878-5MG
142796-24-5
5MG
¥4669.7 2023-01-14
PhytoLab
82878-50mg
2,3-Dehydrosilybin B
142796-24-5 ≥ 90.0 %
50mg
€1651.5000000000002 2023-10-25
PhytoLab
82878-250mg
2,3-Dehydrosilybin B
142796-24-5 ≥ 90.0 %
250mg
€7798.75 2023-10-25
PhytoLab
82878-500mg
2,3-Dehydrosilybin B
142796-24-5 ≥ 90.0 %
500mg
€14680 2023-10-25
PhytoLab
82878-1000mg
2,3-Dehydrosilybin B
142796-24-5 ≥ 90.0 %
1000mg
€27525 2023-10-25

Additional information on 2,3-dehydrosilybin

Professional Introduction to Compound with CAS No. 142796-24-5 and Product Name: 2,3-dehydrosilybin

The compound with the CAS number 142796-24-5 and the product name 2,3-dehydrosilybin represents a significant advancement in the field of chemobiology and pharmaceutical research. This compound has garnered considerable attention due to its unique structural properties and potential therapeutic applications. 2,3-dehydrosilybin, as a derivative of silybin—a well-known flavonoid with hepatoprotective properties—has been the subject of extensive studies aimed at elucidating its mechanism of action and exploring its pharmacological relevance.

2,3-dehydrosilybin is structurally characterized by a siloxy group incorporated between the C2 and C3 positions of the flavonolignan backbone. This modification imparts distinct chemical and biological properties that distinguish it from its parent compound, silybin. The siloxy group enhances solubility in aqueous media while maintaining the inherent bioactivity of silybin. This dual property makes 2,3-dehydrosilybin an attractive candidate for drug formulation and delivery systems, particularly in contexts where poor solubility of bioactive molecules is a limiting factor.

Recent research has highlighted the potential of 2,3-dehydrosilybin as an antioxidant and anti-inflammatory agent. Studies have demonstrated that this compound exhibits potent radical-scavenging activity, which is attributed to its ability to neutralize reactive oxygen species (ROS) and inhibit oxidative stress-induced cellular damage. In preclinical models, 2,3-dehydrosilybin has shown promise in mitigating liver injury caused by toxins such as carbon tetrachloride and galactosamine. These findings align with the traditional use of silybin in treating liver disorders, suggesting that 2,3-dehydrosilybin may offer enhanced efficacy due to its improved pharmacokinetic profile.

The pharmacological effects of 2,3-dehydrosilybin are not limited to hepatoprotection; emerging evidence suggests that it may also play a role in neuroprotection. Oxidative stress and inflammation are key pathological mechanisms in neurodegenerative diseases such as Alzheimer's and Parkinson's disease. In vitro studies have revealed that 2,3-dehydrosilybin can attenuate neuronal damage induced by beta-amyloid aggregation and mitochondrial dysfunction. Furthermore, animal models have shown that chronic administration of 2,3-dehydrosilybin can delay cognitive decline and reduce neuroinflammation, indicating its potential as a therapeutic agent for neurodegenerative conditions.

Another area of interest is the anti-cancer potential of 2,3-dehydrosilybin. Flavonoids have long been recognized for their ability to modulate cell proliferation and induce apoptosis in cancer cells. Research indicates that 2,3-dehydrosilybin can inhibit the growth of various cancer cell lines by disrupting signaling pathways such as MAPK and PI3K/Akt. Additionally, it has been observed to enhance the sensitivity of cancer cells to chemotherapeutic agents, suggesting a possible role in combination therapy regimens. These findings underscore the versatility of 2,3-dehydrosilybin as a multi-targeted therapeutic agent with implications for both chronic inflammatory diseases and oncology.

The synthesis of 2,3-dehydrosilybin presents unique challenges due to its complex structure. Traditional synthetic routes often involve multi-step organic transformations that require specialized reagents and conditions. However, advancements in synthetic chemistry have enabled more efficient methodologies for producing this compound on a scalable basis. One notable approach involves the use of organosilicon reagents to introduce the siloxy group at the C2-C3 position via a hydrosilation reaction. This method offers high selectivity and yield, making it suitable for industrial-scale production.

The development of novel drug delivery systems has been an integral part of optimizing the therapeutic potential of 2,3-dehydrosilybin. Lipid-based nanoparticles have emerged as a promising platform for delivering hydrophobic bioactive molecules like 2,3-dehydrosilybin into target tissues. These nanoparticles enhance bioavailability by improving solubility and protecting the compound from metabolic degradation. Preliminary clinical trials have demonstrated that formulations containing lipid nanoparticles loaded with 2,3-dehydrosilybin exhibit prolonged circulation times and targeted delivery to affected tissues.

Regulatory considerations are also critical in advancing 2,3-dehydrosilybin from preclinical to clinical use. Compliance with Good Manufacturing Practices (GMP) ensures that pharmaceutical-grade material is produced consistently under controlled conditions. Additionally, toxicological studies are essential to assess safety margins and establish dosing regimens for human trials. Collaborative efforts between academic researchers and pharmaceutical companies are necessary to navigate these regulatory pathways efficiently.

The future prospects for 2,3-dehydrosilybin are promising given its multifaceted therapeutic potential. Ongoing research aims to further elucidate its mechanism of action across different biological pathways while exploring novel applications such as anti-viral and anti-microbial agents. The integration of computational modeling with experimental validation will accelerate the discovery process by predicting drug interactions and optimizing lead compounds.

In conclusion,2,3-dehydrosilybin, identified by CAS No. 142796-24-5, represents a significant advancement in chemobiology with applications spanning hepatoprotection, neuroprotection,and oncology.* Its unique structural features,* enhanced solubility,*and potent biological activity make it a compelling candidate for future therapeutics.* Continued research*and development efforts*are poised*to unlock*its full potential*and contribute*to improving*human health outcomes.*

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