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Anacardic Acid (CAS 16611-84-0)

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Synonym:6-Pentadecylsalicylic acid
Application:A multi-use enzyme activator and inhibitor
CAS Number:16611-84-0
Purity:≥95%
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
Description
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).
Usage
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
SMILES:CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
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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