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A7236

Sigma-Aldrich

Anacardic acid

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Synonym(s):
2-Hydroxy-6-pentadecylbenzoic acid, 22:0-Anacardic acid, 6-Pentadecylsalicylic acid
Empirical Formula (Hill Notation):
C22H36O3
CAS Number:
Molecular Weight:
348.52
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: ≥20 mg/mL

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCc1cccc(O)c1C(O)=O

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)

InChI key

ADFWQBGTDJIESE-UHFFFAOYSA-N

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This Item
UC305PHR2470172050
vibrant-m

A7236

Anacardic acid

vibrant-m

UC305

O-Desmethylnaproxen

vibrant-m

PHR2470

6-Hydroxynicotinic acid

vibrant-m

172050

Anacardic Acid

Quality Level

100

Quality Level

200

Quality Level

300

Quality Level

100

solubility

DMSO: ≥20 mg/mL

solubility

-

solubility

-

solubility

DMSO: 10 mg/mL, ethanol: 10 mg/mL, methanol: 10 mg/mL

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-30°C

storage temp.

2-8°C

color

white to beige

color

white

color

-

color

white

storage condition

protect from light

storage condition

-

storage condition

-

storage condition

OK to freeze, protect from light

Application

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

Biochem/physiol Actions

Anacardic acid is a natural bioactive compound derived from the nutshell of Anacardium occidentale. It possesses anti-fungal, anti-bacterial, anti-termite, and molluscicidales activities. Anacardic acid acts as a therapeutic agent against obesity, cancer, inflammatory disorders, and oxidative damage. It functions as an inhibitor of various enzymes such as lipoxygenase (LOX-1), xanthine oxidase, nuclear factor κ B (NFκB) kinase, tyrosinase, and ureases.
Anacardic acid is a HAT (Histone Acetyltransferase) inhibitor.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

related product

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Mahadevappa Hemshekhar et al.
Basic & clinical pharmacology & toxicology, 110(2), 122-132 (2011-11-23)
Anacardic acid (AA) is a bioactive phytochemical found in nutshell of Anacardium occidentale. Chemically, it is a mixture of several closely related organic compounds, each consisting of salicylic acid substituted with an alkyl chain. The traditional Ayurveda depicts nutshell oil
Mingxi Li et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(30), 3885-3892 (2009-10-16)
Global histone modifications and their putative relevance to short and long term cellular programming have drawn substantial interest in the study of chromatin. Here we describe the use of reverse-phase liquid chromatography coupled to Linear Ion Trap-Fourier Transform Mass Spectrometry
ZhenHua Ni et al.
Respiratory research, 12, 47-47 (2011-04-15)
"Phosphatase and tensin homolog deleted on chromosome 10" (PTEN) is mostly considered to be a cancer-related gene, and has been suggested to be a new pathway of pathogenesis of asthma. The purpose of this study was to investigate the effects
B Devipriya et al.
Journal of molecular graphics & modelling, 34, 57-66 (2012-02-07)
A charge density analysis has been performed on gas phase and docked forms of anacardic acid molecule to understand its charge density distribution, electrostatic moments and the conformation in the active site of p300 enzyme. Here, we report the binding
Massimo Ghizzoni et al.
European journal of medicinal chemistry, 47(1), 337-344 (2011-11-22)
Histone acetyltransferases are important enzymes that regulate various cellular functions, such as epigenetic control of DNA transcription. Development of HAT inhibitors with high selectivity and potency will provide powerful mechanistic tools for the elucidation of the biological functions of HATs

Articles

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