Cas no 87402-84-4 (Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]-)

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- structure
87402-84-4 structure
Product Name:Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]-
CAS No:87402-84-4
MF:C21H22O4
MW:338.396986484528
CID:656639
PubChem ID:9819225
Update Time:2025-11-02

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]-
    • (E)-2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-styrylbenzoic acid
    • Cajanine
    • 2-Hydroxy-4-methoxy-3-(3-methyl-2-buten-1-yl)-6-[(1E)-2-phenylethenyl]benzoic acid (ACI)
    • Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethenyl)-, (E)- (ZCI)
    • Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- (9CI)
    • (E)-Longistyline A carboxylic acid
    • 3-Hydroxy-4-prenyl-5-methoxystilbene-2-carboxylic acid
    • Cajaninstilbene acid
    • Longistyle
    • CHEMBL3596977
    • SCHEMBL6227923
    • AKOS040734182
    • NCGC00385333-01
    • FS-8514
    • 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-[(E)-2-phenylethenyl]benzoic acid
    • 87402-84-4
    • CHEBI:174548
    • DTXSID701315168
    • 2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-[(E)-2-phenylethenyl]benzoic Acid
    • (E)-2-Hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-styrylbenzoic acid
    • 2-Hydroxy-4-methoxy-3-prenyl-6-styrylbenzoic acid
    • NS00097169
    • Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-buten-1-yl)-6-[(1E)-2-phenylethenyl]-
    • EX-A6194
    • 2-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethenyl)benzoic acid
    • Inchi: 1S/C21H22O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-11,13,22H,12H2,1-3H3,(H,23,24)/b11-10+
    • InChI Key: XPDYDSQPCFQSLH-ZHACJKMWSA-N
    • SMILES: C(/C1C=C(OC)C(C/C=C(\C)/C)=C(O)C=1C(=O)O)=C\C1C=CC=CC=1

Computed Properties

  • Exact Mass: 338.15180918g/mol
  • Monoisotopic Mass: 338.15180918g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 6
  • Complexity: 486
  • 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
  • XLogP3: 5.8
  • Topological Polar Surface Area: 66.8?2

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Pricemore >>

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87402-84-4 >=98%
5mg
$318 2023-09-19

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Methanol ;  8 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6, rt
Reference
Synthesis and Biological Evaluation of Cajaninstilbene Acid and Amorfrutins A and B as Inhibitors of the Pseudomonas aeruginosa Quorum Sensing System
Xu, Xing-Jun; Zeng, Ting; Huang, Zhi-Xing; Xu, Xiao-Fang; Lin, Jing ; et al, Journal of Natural Products, 2018, 81(12), 2621-2629

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  2 h, rt → 90 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2
Reference
Novel cajaninstilbene acid derivatives as antibacterial agents
Geng, Zhi-Zhong; Zhang, Jian-Jun; Lin, Jing; Huang, Mei-Yan; An, Lin-Kun; et al, European Journal of Medicinal Chemistry, 2015, 100, 235-245

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux
Reference
A facile synthesis of cajaninstilbene acid and its derivatives
Chen, Qi; Lu, Kuo; Zheng, Chang; Xu, Xiao-Fang; Lin, Jing; et al, Chinese Chemical Letters, 2019, 30(8), 1527-1529

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  2 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C
Reference
Design and Synthesis of Cajanine Analogues against Hepatitis C Virus through Down-Regulating Host Chondroitin Sulfate N-Acetylgalactosaminyltransferase 1
Ji, Xing-Yue; Chen, Jin-Hua; Zheng, Guang-Hui; Huang, Meng-Hao; Zhang, Lei; et al, Journal of Medicinal Chemistry, 2016, 59(22), 10268-10284

Production Method 5

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran ,  Water ;  32 h, 50 °C
1.2 Reagents: Sodium hydroxide ,  Water Solvents: Water ;  neutralized, rt
Reference
A Common Building Block for the Syntheses of Amorfrutin and Cajaninstilbene Acid Libraries toward Efficient Binding with Peroxisome Proliferator-Activated Receptors
Aidhen, Indrapal S.; Mukkamala, Ramesh; Weidner, Christopher; Sauer, Sascha, Organic Letters, 2015, 17(2), 194-197

Production Method 6

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ;  1 h, 21 psi, 89 - 91 °C
Reference
Total synthesis of cajanine and its antiproliferative activity against human hepatoma cells
Ji, Xing-Yue; Xue, Si-Tu; Zheng, Guang-Hui; Han, Yan-Xing; Liu, Zong-Ying; et al, Acta Pharmaceutica Sinica B, 2011, 1(2), 93-99

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Raw materials

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Preparation Products

Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- Suppliers

Hubei Cuiyuan Biotechnology Co.,Ltd
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(CAS:87402-84-4)Cajanine
Order Number:CRN0490
Stock Status:in stock
Quantity:5mg/20mg/50mg
Purity:≥98%
Pricing Information Last Updated:Friday, 14 March 2025 10:55
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Additional information on Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]-

Recent Advances in the Study of Benzoic Acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- (CAS: 87402-84-4)

The compound Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]-, with the CAS number 87402-84-4, has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This molecule, characterized by its unique structural features, including a hydroxy-methoxy benzoic acid core and a prenyl-styryl side chain, has shown promising biological activities. Recent studies have focused on its potential applications in drug development, particularly in the areas of anti-inflammatory, anticancer, and antimicrobial therapies.

One of the key findings from recent research is the compound's ability to modulate inflammatory pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that 87402-84-4 effectively inhibits the NF-κB signaling pathway, which plays a critical role in inflammation and immune responses. The study utilized in vitro models of human macrophages and in vivo murine models of inflammation, showing significant reduction in pro-inflammatory cytokines such as TNF-α and IL-6. These results suggest that the compound could be a potential candidate for developing novel anti-inflammatory drugs.

In addition to its anti-inflammatory properties, 87402-84-4 has also been investigated for its anticancer potential. A recent study in Bioorganic & Medicinal Chemistry Letters explored the compound's effects on various cancer cell lines, including breast, lung, and colon cancers. The research highlighted that the compound induces apoptosis in cancer cells through the activation of caspase-3 and PARP cleavage. Furthermore, molecular docking studies revealed that 87402-84-4 interacts with key oncogenic targets, such as EGFR and PI3K, suggesting a multi-targeted mechanism of action. These findings open new avenues for the development of targeted cancer therapies.

Another area of interest is the antimicrobial activity of 87402-84-4. A 2024 study published in Antimicrobial Agents and Chemotherapy reported that the compound exhibits broad-spectrum activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). The study also identified that the compound disrupts bacterial cell membrane integrity, leading to cell lysis. Given the rising threat of antibiotic resistance, these findings are particularly relevant and could contribute to the development of new antimicrobial agents.

Despite these promising results, challenges remain in the clinical translation of 87402-84-4. Pharmacokinetic studies indicate that the compound has limited bioavailability, which may hinder its therapeutic efficacy. Recent efforts have focused on structural modifications and formulation strategies to improve its solubility and stability. For instance, a 2023 patent application described the synthesis of prodrug derivatives of 87402-84-4, which showed enhanced oral bioavailability in preclinical models. These advancements are critical for moving the compound from bench to bedside.

In conclusion, the latest research on Benzoic acid,2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-[(1E)-2-phenylethenyl]- (CAS: 87402-84-4) underscores its potential as a multi-functional therapeutic agent. Its anti-inflammatory, anticancer, and antimicrobial properties make it a valuable candidate for further drug development. However, addressing its pharmacokinetic limitations will be essential for its successful clinical application. Future studies should focus on optimizing its chemical structure and exploring synergistic effects with existing drugs to maximize its therapeutic potential.

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