Anacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain.1 These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (pCAF) with IC50 values of 8.5 and 5 µM, respectively.2 At 25 µmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.3
1
Satoh, M., Takeuchi, N., Fujita, T., et al. Synthesis of anacardic acids utilizing an annelation reaction of isoxazoles with ethyl acetoacetate. Chem Pharm Bull46(10)1501-1505(1998).
2
Balasubramanyam, K., Swaminathan, V., Ranganathan, A., et al. Small molecule modulators of histone acetyltransferase p300. J Biol Chem278(21)19134-19140(2003).
3
Sung, B., Pandey, M.K., Ahn, K.S., et al. Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-κB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-κBα kinase, leading to potentiation of apoptosis. Blood1114880-4891(2008).
Synonyms
6-pentadecyl Salicylic Acid
Formal Name
2-hydroxy-6-pentadecyl-benzoic acid
CAS Number
16611-84-0
Molecular Formula
C22H36O3
Formula Weight
348.5
Formulation
A crystalline solid
Purity
≥98%
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCCCCCCCCc1cccc(O)c1C(=O)O
Background Reading
Satoh, M., Takeuchi, N., Fujita, T., et al. Synthesis of anacardic acids utilizing an annelation reaction of isoxazoles with ethyl acetoacetate. Chem Pharm Bull46(10)1501-1505(1998).
Balasubramanyam, K., Swaminathan, V., Ranganathan, A., et al. Small molecule modulators of histone acetyltransferase p300. J Biol Chem278(21)19134-19140(2003).
Sung, B., Pandey, M.K., Ahn, K.S., et al. Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-κB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-κBα kinase, leading to potentiation of apoptosis. Blood1114880-4891(2008).
Anacardic Acid is available in the following screening
library: