6-pentadecylsalicylic acid Chemical Properties

Melting point:

90-91℃

Boiling point:

474.8±33.0 °C(Predicted)

Density 

1.002

storage temp. 

-20°C

solubility 

DMSO: ≥20mg/mL

pka

3.08±0.30(Predicted)

form 

White solid

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

InChI

InChI=1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)

InChIKey

ADFWQBGTDJIESE-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=C(CCCCCCCCCCCCCCC)C=CC=C1O

LogP

9.960 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

6-pentadecylsalicylic acid Usage And Synthesis

Description

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. 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. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.

Chemical Properties

Powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Ginkgo biloba.

Uses

2-Hydroxy-6-pentadecyl Benzoic Acid, is a compound that is used to treat agriculture from various fruit insects. Derivative of this molecule has been also shown to be a potent activator of human 5-lipoxygenases (5-LOX).

Uses

Anacardic acid has been used:

• as a histone acetylase (HAT) inhibitor to study its effects on rat cortical neurons
• as a positive control in acetylation assay in vitro
• as an acetylase inhibitor to study its effects on the ribonucleic acid export 1 (Rae-1) protein acetylation that was transfected in human embryonic kidney cells

Uses

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. 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. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.[Cayman Chemical]

Definition

ChEBI: Anacardic acid is a hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities. It has a role as an EC 2.3.1.48 (histone acetyltransferase) inhibitor, an apoptosis inducer, a neuroprotective agent, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, an antibacterial agent, an anti-inflammatory agent and a plant metabolite. It is a hydroxybenzoic acid and a hydroxy monocarboxylic acid. It is functionally related to a salicylic acid.

General Description

A cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC₅₀ = 2.2 μM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 μM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.

Biochem/physiol Actions

Target IC50: 5 μM against HAT; 8.5 μM against PCAF; 2.2 μM inhibiting protein SUMO modification using RanGAP1-C2 as substrate

in vitro

lncap, a classical metastatic prostate adenocarcinoma cell line, was adopted to study the effect of aa on cell growth, cycles and apoptosis. it was found that 125 m aa significantly inhibited lncap cell proliferation. in addition, the g1/s cell cycles arrest and the apoptosis of lncap cell was induced. further mechanistic study suggested that aa induced cell apoptosis via suppressing p300. [1]

in vivo

diesel exhaust particle- (dep-) induced lung inflammation model was established to study the effect of aa on inflammation in mice. ten days before dep-instillation stimulation, mice were orally pretreated with 50, 150, or 250 mg/kg of aa for thirty days. all doses of aa ameliorated activities of oxidative enzymes. moreover, 50 mg/kg of aa significantly decreased the expression level of tumor necrosis factor in lung. [2]

IC 50

noncompetitively inhibit histone acetyltransferase (hat) activity in prostate cancer with an ic50 value of about 5.0 m.

storage

-20°C

References

[1] KARANAM BALASUBRAMANYAM. Small molecule modulators of histone acetyltransferase p300.[J]. The Journal of Biological Chemistry, 2003, 278 21: 19134-19140. DOI:10.1074/jbc.m301580200
[2] YINGLI SUN. Inhibition of histone acetyltransferase activity by anacardic acid sensitizes tumor cells to ionizing radiation[J]. FEBS Letters, 2006, 580 18: 4353-4356. DOI:10.1016/j.febslet.2006.06.092
[3] YUANYUAN WU. Anacardic acid (6-pentadecylsalicylic acid) inhibits tumor angiogenesis by targeting Src/FAK/Rho GTPases signaling pathway.[J]. Journal of Pharmacology and Experimental Therapeutics, 2011, 339 2: 403-411. DOI:10.1124/jpet.111.181891
[4] ATHIRA OMANAKUTTAN. Anacardic acid inhibits the catalytic activity of matrix metalloproteinase-2 and matrix metalloproteinase-9.[J]. Molecular Pharmacology, 2012, 82 4: 614-622. DOI:10.1124/mol.112.079020
[5] BOKYUNG SUNG. 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.[J]. Blood, 2008: 4880-4891. DOI:10.1182/blood-2007-10-117994

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