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A7236

Sigma-Aldrich

Anacardic acid

Synonym(s):

2-Hydroxy-6-pentadecylbenzoic acid, 22:0-Anacardic acid, 6-Pentadecylsalicylic acid

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About This Item

Empirical Formula (Hill Notation):
C22H36O3
CAS Number:
16611-84-0
Molecular Weight:
348.52
MDL number:
MFCD07368254
UNSPSC Code:
12352106
PubChem Substance ID:
329770923
NACRES:
NA.77

form

powder

Quality Level

100

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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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Ishwariya Venkatesh et al.
Neuroepigenetics, 8, 19-26 (2016-12-19)
Axon regeneration in adult central nervous system (CNS) is limited in part by a developmental decline in the ability of injured neurons to re-express needed regeneration associated genes (RAGs). Adult CNS neurons may lack appropriate pro-regenerative transcription factors, or may
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
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