2-hydroxy-6-pentadecylbenzoic acid

• ChemBase ID: 154587
• Molecular Formular: C22H36O3
• Molecular Mass: 348.51944
• Monoisotopic Mass: 348.26644501
• SMILES: CCCCCCCCCCCCCCCc1cccc(c1C(=O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCc1cccc(c1C(=O)O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-6-pentadecylbenzoic acid
• IUPAC Traditional name: 6-pentadecylsalicylic acid
• Synonyms: 22:0-Anacardic acid; 2-Hydroxy-6-pentadecylbenzoic acid; 6-Pentadecylsalicylic acid; Anacardic acid

Database IDs

• CAS Number: 16611-84-0
• MDL Number: MFCD07368254
• PubChem SID: 162248725
• PubChem CID: 167551

CALCULATED PROPERTIES

• Acid pKa: 2.6407335
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.93889
• LogD (pH = 7.4): 5.210031
• Log P: 8.714646
• Molar Refractivity: 104.7503 cm^3
• Polarizability: 40.810604 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to beige powder

Safety Information

• Storage Condition: protect from light; under inert gas
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H36O3

DETAILS

Sigma Aldrich - A7236

Biochem/physiol Actions
Anacardic acid is a HAT (Histone Acetyltransferase) inhibitor.
Application
Anacardic acid is a histone acetyltransferase (HAT) inhibitor. Anacardic acid has bactericide, fungicide, insecticide, anti-termite and molluscicide properties and acts as a therapeutic agent in the treatment of pathophysiological disorders such as cancer, oxidative damage, inflammation and obesity. Anacardic acid is a common inhibitor of several clinically targeted enzymes such as NFκB kinase, histone acetyltransferase (HATs), lipoxygenase (LOX-1), xanthine oxidase, tyrosinase and ureases.