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Anacardic Acid (CAS 16611-84-0)

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Synonym:6-Pentadecylsalicylic acid
Application:Shown to potently inhibit HAT-dependent transcription and SUMOylation
CAS Number:16611-84-0
Molecular Weight:348.52
Molecular Formula:C22H36O3
Refer to Certificate of Analysis for lot specific data (including water content).
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Product NameCatalog #UnitPriceQtyAddFavorites
Anacardic Acid sc-202463 5 mg $41
Anacardic Acid sc-202463A 25 mg $157
Anacardic Acid is a pentadecane aliphatic chain containing hydroxylcarboxylic acid. The acid is an effective inhibitor of the activities of p300, p300/CBP associated factor histone acetyltransferase, prostaglandin synthase (PTGS2 or Cox-2), tyrosinase, urease-α and -β, lipoxygenase (LO), and xanthine oxidase. Additionally, it has been shown to potently inhibit HAT-dependent transcription and SUMOylation, as well as decrease expression of NF-κB regulated gene products at high concentrations. Research suggests that anacardic acid is a potent activator of ARK-1 (Aurora kinase A) mediated phosphorylation of histone H3 while leaving ARK-2 unaffected in vitro. Anacardic acid has demonstrated bactericidal activity against methicillin-resistant Staphylococcus aureus (MRSA).
Stock solutions are stable for up to 3 months when stored at -20°C.
Technical Information
Physical State:solid
Derived from:Synthetic
Solubility:Soluble in ether, petroleum ether, DMSO (≥20 mg/mL), DMF (~10 mg/mL), ethanol (~10 mg/mL), a1:1 solution of ethanol:PBS(pH7.2) (~0.5 mg/ml), methanol, dichloromethane, and ethyl acetate.
Storage:Store at 4° C
Melting Point:33.9-37.2° C
Boiling Point:474.82° C at 760 mmHg
Density:1.00 g/cm3
Refractive Index:n20D 1.52
IC50:PCAF: IC50 = 8.5 µM; HAT: IC50 = 5 µM; HIV-1(RF): IC50 = 49.35 µM (CEM-SS); HIV-1(RF): EC5050 = >61.69 µM (CEM-SS); Protein SUMO and modification: IC50 = 2.2 µM
Safety and Reference Information
WGK Germany:1
PubChem CID:167551
Merck Index:14: 621
MDL Number:MFCD07368254
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Anacardic Acid Product Reviews

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1. Muroi, H., et al., 1996. Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus. The Journal of applied bacteriology. 80(4): 387-94. PMID: 8849640
2. Paramashivappa, R., et al., 2002. Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition. Journal of agricultural and food chemistry. 50(26): 7709-13. PMID: 12475293
3. Balasubramanyam, Karanam., et al., 2003. Small molecule modulators of histone acetyltransferase p300. The Journal of biological chemistry. 278(21): 19134-40. PMID: 12624111
4. Kishore, A Hari., et al., 2008. Specific small-molecule activator of Aurora kinase A induces autophosphorylation in a cell-free system. Journal of medicinal chemistry. 51(4): 792-7. PMID: 18215015
5. Sung, Bokyung., et al., 2008. Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kappaB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-kappaBalpha kinase, leading to potentiation of apoptosis. Blood. 111(10): 4880-91. PMID: 18349320
6. Fukuda, Isao., et al., 2009. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chemistry & biology. 16(2): 133-40. PMID: 19246003
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