Anacardic acid

Base Information

• Chemical Name: Anacardic acid
• CAS No.: 16611-84-0
• Molecular Formula: C22H36O3
• Molecular Weight: 348.526
• Hs Code.: 2918290000
• European Community (EC) Number: 234-268-7,683-602-1
• NSC Number: 623096,333857,229596
• UNII: 8H693KBS2W
• DSSTox Substance ID: DTXSID00168078
• Nikkaji Number: J167.336J
• Metabolomics Workbench ID: 43980
• ChEMBL ID: CHEMBL33778
• Mol file: 16611-84-0.mol

Synonyms:2-hydroxy-6-pendadecylbenzoic acid;6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid;6-(8,11,14-pentadecatrienyl)salicylic acid;6-nonadecyl salicylic acid;6-pentadecyl salicylic acid;6-pentadecylsalicylic acid;anacardic acid

Chemical Property of Anacardic acid

Chemical Property:

• Vapor Pressure: 8.02E-10mmHg at 25°C
• Melting Point: 90-91℃
• Refractive Index: 1.514
• Boiling Point: 324.5 °C at 760 mmHg
• PKA: 3.08±0.30(Predicted)
• Flash Point: 150.1 °C
• PSA: 57.53000
• Density: 1.432 g/cm³
• LogP: 6.72410
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 9.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 348.26644501
• Heavy Atom Count: 25
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

2-Hydroxy-6-pentadecylBenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• 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.
• Uses: Anacardic acid has been used: as a histone acetylase (HAT) inhibitor to study its effects on rat cortical neuronsas a positive control in acetylation assay in vitroas 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 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] 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).

Technology Process of Anacardic acid

There total 43 articles about Anacardic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

6-(8-pentadecenyl)salicylic acid (22910-60-7) → 6-Pentadecylsalicylic Acid (16611-84-0)

Guidance literature:

With palladium 10% on activated carbon; In ethyl acetate; at 20 ℃; Inert atmosphere;

DOI:10.1039/c8cc05595e

Reference yield: 95.0%

2,2-dimethyl-5-pentadecyl-4H-benzo[d][1,3]dioxin-4-one → 6-Pentadecylsalicylic Acid (16611-84-0)

Guidance literature:

With potassium hydroxide; In water; dimethyl sulfoxide; at 80 ℃; for 1h;

DOI:10.1021/jo962423i

Reference yield: 94.0%

6-pentadecylsalicylic acid methyl ester (38449-27-3) → 6-Pentadecylsalicylic Acid (16611-84-0)

Guidance literature:

With potassium hydroxide; In ethanol; Heating;

upstream raw materials:

6-(8-pentadecenyl)salicylic acid

(15 : 0)-anacardic acid O-methyl ether

6-pentadecylsalicylic acid methyl ester

2-Methoxy-6-pentadecyl-benzoic acid ethyl ester

Downstream raw materials:

ethyl 6-pentadecylsalicylate

6-pentadecylsalicylic acid methyl ester

anacardic anilide

(15 : 0)-anacardic acid O-methyl ether

Refernces

• 1、 Morimoto,Kawamatsu,Sugihara. "Stereo-structure of toxin from the fruit of Ginkgo biloba L.". . p. 2282 - 2286. Retrieved 1968.
• 2、 Brackett, Christopher M.,García-Casas, Ana,Castillo-Lluva, Sonia,Blagg, Brian S. J.. "Synthesis and Evaluation of Ginkgolic Acid Derivatives as SUMOylation Inhibitors". . p. 2221 - 2226. Retrieved 2020/12/17.
• 3、 Rambabu,Dubey,Ram,Balram. "Synthesis, characterization and antimicrobial evaluation of (E)-N'-[(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl]-methylene)benzohydrazide derivatives". . p. 175 - 180. Retrieved 2016/01/20.