Anacardic Acid (Hydroginkgolic acid), a natural product isolated from cashew nut shell liquid, is a potent inhibitor of p300 and p300/CBP-associated factor histone acetyltranferases, which also has antibacterial activity, antimicrobial activity, prostaglandin synthase inhibition, and tyrosinase and lipoxygenase inhibition. Anacardic acid regulates the activity and expression of several other crucial enzymes including NFκB kinase, lipoxygenase (LOX-1), xanthine oxidase, tyrosinase and ureases. Therefore, this compound exerts anti-oxidation, anti-inflammation and anti-tumor activities in vitro and in vivo.

Physicochemical Properties

Molecular Formula	C22H36O3
Molecular Weight	348.52
Exact Mass	348.266
CAS #	16611-84-0
Related CAS #	16611-84-0
PubChem CID	167551
Appearance	White to off-white solid powder
Density	1.0±0.1 g/cm3
Boiling Point	474.8±33.0 °C at 760 mmHg
Melting Point	90-91℃
Flash Point	255.1±21.9 °C
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.515
LogP	9.96
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	15
Heavy Atom Count	25
Complexity	329
Defined Atom Stereocenter Count	0
InChi Key	ADFWQBGTDJIESE-UHFFFAOYSA-N
InChi Code	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)
Chemical Name	2-Hydroxy-6-pentadecyl-benzoic acid
Synonyms	6-pentadecylsalicylic Acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Histone acetyltransferase anacardic acid (IC50 of ~8.5 μM and ~5 μM, respectively) inhibits the HAT activities of p300 and PCAF [1]. Hyphalite growth is inhibited by anacardic acid (300 μM). In M, anacardic acid (50 μM) causes apoptosis-like traits. oryzae; caspase has no bearing on its function. Mitochondrial potential is lost when exposed to anacardic acid (1–80 μM). Antioxidant action is demonstrated by anacardic acid (1-60 μM) in M. oryzae.
ln Vivo	Anacardic acid (5 mg/kg, ip) attenuates HAT binding to the MEF2A promoter and rescues phenylephrine-induced H3K9ac hyperacetylation in C57BL/6 mice. Anacardic Acid inhibits the transcription levels of MEF2A and cardiac development-related downstream genes, attenuates the protein overexpression of cardiac downstream genes caused by phenylephrine, reverses and attenuates cardiac hypertrophy in the hearts of mice exposed to phenylephrine, and attenuates left ventricular pressure and improve cardiac function in mice with cardiac hypertrophy [2].
Animal Protocol	Dissolved in DMSO and co-injected with ethanol; 0, 1.25, 2.5, 5, 10 mg/kg; i.p. injection Kunming mice
References	[1]. Small molecule modulators of histone acetyltransferase p300. J Biol Chem. 2003 May 23;278(21):19134-40. Epub 2003 Mar 6. [2]. Phenylephrine-induced cardiac hypertrophy is attenuated by a histone acetylase inhibitor anacardic acid in mice. Mol Biosyst. 2017 Mar 28;13(4):714-724. [3]. Anacardic acid induces apoptosis-like cell death in the rice blast fungus Magnaporthe oryzae. Appl Microbiol Biotechnol. 2016 Jan;100(1):323-35.
Additional Infomation	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. Anacardic acid has been reported in Ozoroa insignis, Knema elegans, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 69 mg/mL (198 mM) Water:<1 mg/mL Ethanol: N/A

Solubility (In Vivo)

Solubility in Formulation 1: 10 mg/mL (28.69 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 100.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (7.17 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.17 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.8693 mL	14.3464 mL	28.6928 mL
	5 mM	0.5739 mL	2.8693 mL	5.7386 mL
	10 mM	0.2869 mL	1.4346 mL	2.8693 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.