20261-38-5

Basic information

• Product Name: Ginkgolic acid (13:0)
• Synonyms: 6-n-tridecylsalicylic acid;6-Tridecylsalicylic acid;Ginkgoneolic acid;Ginkgolic Acids (C13:0);C13:0;Ginkgoneolic acid 6-Tridecylsalicylic acid;GA13:0;Ginkgolic Acid 13:0 〔Anacardic Acid 13:0〕
• CAS NO: 20261-38-5
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.47
• Mol File: 20261-38-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 449.488 °C at 760 mmHg
• Flash Point: 239.771 °C
• Appearance: /
• Density: 1.018 g/cm³
• Vapor Pressure: 7.26E-09mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 2-8°C
• PKA: 3.08±0.30(Predicted)
• CAS DataBase Reference: Ginkgolic acid (13:0)(CAS DataBase Reference)
• NIST Chemistry Reference: Ginkgolic acid (13:0)(20261-38-5)
• EPA Substance Registry System: Ginkgolic acid (13:0)(20261-38-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 20261-38-5(Hazardous Substances Data)

Usage

Uses

Ginkgoneolic Acid is a natural mutagenic, carcinogenic and genotoxic agent. An isolate from Ginkgo Biloba leaf, used in traditional medicines treating inflammation and cell proliferation.

InChI:InChI=1/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-14-17-15-13-16-18(21)19(17)20(22)23/h13,15-16,21H,2-12,14H2,1H3,(H,22,23)

Upstream product

• 63125-05-3 Methyl 2-hexadecynoate 
• 63125-03-1 Methyl 3-oxo-2-(triphenylphosphoranylidene)hexadecanoate 
• 592-41-6 1-hexene 
• 2437-56-1 1-tridecene 
• 164014-40-8 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 303-07-1 2,6-Dihydroxybenzoic acid 
• 75808-38-7 Methyl 2-hydroxy-6-tridecylbenzoate 

Downstream Products

• 75808-38-7 Methyl 2-hydroxy-6-tridecylbenzoate 

Relevant articles and documents

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

A convenient and sustainable three-step synthesis of the tyrosinase inhibitor 2-hydroxy-6-tridecylbenzoic acid was developed that starts directly from the anacardic acid component of natural cashew nutshell liquid (CNSL). Natural CNSL contains 60-70% of anacardic acid as a mixture of several double bond isomers. The anacardic acid component was converted into a uniform starting material by ethenolysis of the entire mixture and subsequent selective precipitation of 6-(ω-nonenyl)salicylic acid from cold pentane. The olefinic side chain of this intermediate was elongated by its cross-metathesis with 1-hexene using a first generation Hoveyda-Grubbs catalyst, which was reused as precatalyst in a subsequent hydrogenation step. Overall, the target compound was obtained in an overall yield of 61% based on the unsaturated anacardic acid content and 34% based on the crude CNSL.

Novel chemical synthesis of ginkgolic acid (13:0) and evaluation of its tyrosinase inhibitory activity

A novel efficient synthesis of ginkgolic acid (13:0) from abundant 2,6-dihydroxybenzoic acid was successfully developed through a state-of-the-art palladium-catalyzed cross-coupling reaction and catalytic hydrogenation with an overall yield of 34% in five steps. The identity of the synthesized ginkgolic acid (13:0) was confirmed by nuclear magnetic resonance, mass spectrometry, infrared, and high-performance liquid chromatography. The reaction sequence of this method can be readily extended to the synthesis of other ginkgolic acids. The synthesized ginkgolic acid (13:0) exhibited promising anti-tyrosinase activity (IC50 = 2.8 mg/mL) that was not correlated to antioxidant activity as probed by 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azino-bis(3- ethylbenzothiazoline-6-sulfonic acid), ferric reducing ability of plasma, and oxygen radical absorbance capacity assays. The synthetic strategy developed in this work will significantly facilitate biological studies of ginkgolic acids that have great potential applications in food and pharmaceuticals.