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
• General Description: 6-Pentadecylsalicylic acid (also known as hydrogenated anacardic acid or hydroginkgolic acid) is one of the long-chain phenols isolated from *Ginkgo biloba* L. with demonstrated antitumor activity. While the study highlights anacardic acid (Ib) as highly effective (+++) against Sarcoma 180 ascites in mice, 6-pentadecylsalicylic acid, being a hydrogenated derivative, shares structural similarities but was not explicitly mentioned as a primary active compound in this context. The research suggests that the antitumor mechanism does not depend on the carboxyl group, implying potential relevance for structurally related compounds like 6-pentadecylsalicylic acid, though further investigation would be needed to confirm its specific activity.

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:

6-pentadecylsalicylic acid methyl ester

(15 : 0)-anacardic acid O-acetate

3-n-Pentadecylphenol

2-methoxy-6-pentadecyl-benzoic acid methyl ester

Refernces

Antitumor principles from Ginkgo biloba L.

10.1248/cpb.35.3016

This research aimed to isolate and identify antitumor principles from Ginkgo biloba L., focusing on their effectiveness against Sarcoma 180 ascites in mice. The study successfully isolated seven long-chain phenols, among which anacardic acid (Ib), bilobol (IIa), and cardanol (IIIa) demonstrated significant antitumor activity, with effectiveness rated as (+++) for Ib, (++) for IIa, and (+++) for IIIa at a dosage of 40 mg/kg/day. The compounds were further purified using high-performance liquid chromatography (HPLC) and characterized through spectral data analysis, which included ultraviolet, infrared, nuclear magnetic resonance, and mass spectrometry. The study concluded that the antitumor activity against Sarcoma 180 ascites does not require the carboxyl group, in contrast to the antimicrobial activity which does.