6-n-Tridecylsalicylic acid
6-n-Tridecylsalicylic acid
CAS: 20261-38-5
Molecular Formula: C20H32O3
6-n-Tridecylsalicylic acid - Names and Identifiers
| Name | 6-n-Tridecylsalicylic acid |
| Synonyms | Ginkgoneolic acid 6-Tridecylsalicylic acid 6-n-Tridecylsalicylic acid 6-n-tridecylsalicylic acid 2-hydroxy-6-tridecylbenzoic acid Ginkgoneolic acid 6-Tridecylsalicylic acid |
| CAS | 20261-38-5 |
| 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) |
| InChIKey | VEPUCZUJLKAVNM-UHFFFAOYSA-N |
6-n-Tridecylsalicylic acid - Physico-chemical Properties
| Molecular Formula | C20H32O3 |
| Molar Mass | 320.47 |
| Density | 1.018±0.06 g/cm3(Predicted) |
| Melting Point | 41-42°C |
| Boling Point | 449.5±33.0 °C(Predicted) |
| Flash Point | 239.8°C |
| Solubility | Methanol-1% glacial acetic acid solution (90:10) is the mobile phase, and the detection wavelength is 310nm (for reference only). |
| Vapor Presure | 7.26E-09mmHg at 25°C |
| Appearance | Powder |
| pKa | 3.08±0.30(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,2-8°C |
| Refractive Index | 1.519 |
| MDL | MFCD01661602 |
| Physical and Chemical Properties | Ginkgo biloba from the family Ginkgo biloba |
6-n-Tridecylsalicylic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29163990 |
6-n-Tridecylsalicylic acid - Reference Information
| Plant source: | Ginkgo biloba |
| pharmacological action | ginkgolic acid has antibacterial effect. In vitro, it can inhibit the growth of Mycobacterium tuberculosis; but the experimental treatment of mice and guinea pigs in vivo has no significant effect. currently known ginkgolic acid in ginkgo biloba extract preparations mainly includes Ginkgolic acid, hydrogenated Hydroginkgolic acid, hydrogenated ginkgo acid (Hydroginkgolinicacid,c) and ginkgo new acid. the structure of each compound is similar to urushiol, the sensitizer in raw lacquer, and this structure is the root of sensitization. the more double chains on the hydrocarbon group, the more easily sensitized. |
| physical properties | needle crystal (petroleum ether), melting point 41~42. IR γ Filmmax cm -1: 1645 (COOH), 1610 (aromatic ring). |
| Physiological toxicity and adverse reactions of ginkgolic acid | Foreign studies have reported that ginkgolic acid in ginkgo biloba extract has potential sensitization and mutagenicity, and strong cytotoxicity, which can cause severe allergic reactions, gene mutations, and nerve damage, lead to nausea and heartburn, anaphylactic shock, allergic purpura, exfoliative dermatitis, gastrointestinal mucosal allergy, spasm and nerve paralysis and other adverse reactions. in a retrospective study of german ginkgo biloba extract EGb761, 9 out of 8505 patients with gastrointestinal adverse reactions were reported. Therefore, ginkgolic acid is considered as a toxic and side effect component, and its content should be strictly limited in the preparation. Related studies also believe that although the content of ginkgolic acid in ginkgo biloba preparations is controlled below 5ppm, adverse reactions are still occasionally occurred. Clinical reports involving adverse reactions caused by ginkgolic acid are: ①Gastrointestinal adverse effects: Ginkgo biloba extract The most common adverse reactions of preparations are generally mild or transient, but two patients were found to interrupt treatment due to severe nausea and vomiting. ② There are 10 cases of allergic reactions reported, mainly including the following 7 kinds: skin itching, vascular swelling, allergic purpura, allergic cough, exfoliative dermatitis, acute urticaria, phlebitis. ③ The other 3 cases reported granulocytopenia, hypertension and central nervous system excitement. |
| Plant source | Ginkgo biloba is an ancient and primitive relict species that has grown on the earth for about 0.2 billion years and is called "living fossil. China is the hometown of ginkgo. The Chinese History Museum displays the image of "Peking Man" eating ginkgo 40-500,000 years ago. At present, China's ginkgo resources account for 70% of the world. Ginkgo biloba is used as a Chinese herbal medicine in the folk. It was first seen in the "Daily Materia Medica" in the 14th century. It is mainly used for cough, asthma and inflammation. ginkgolic acid is a product extracted from Ginkgo biloba l. leaves. commercial extracts are usually standardized to contain flavonol glycoside 24% and ginkgolide 6%. |
| separation and purification | process flow chart of separation and purification of ginkgolic acid from dried seeds of ginkgo |
| determination of ginkgolic acid content in ginkgo biloba leaves | [chromatographic conditions] reversed phase silver chromatography column: KFC18 column (250mm × 4.6mm,7 μm); Mobile phase: methanol-5% acetic acid (90:10), add AgNO3 to make [Ag +] 0.03mol/L; Flow rate: 1.0 ml/min; Detection wavelength: 310nm; Column temperature: 30 ℃. [preparation of test product] take about 1.0g of dry product, weigh it accurately, place it in a 100ml flask, soak it with 40ml of anhydrous ethanol, heat reflux, filter, wash the flask and filter residue twice with leaching agent, combine filtrate and washing solution, and fix the volume to 50ml. Accurately suck 1ml into the test tube with plug, add 3ml of n-hexane, appropriate amount of sulfuric acid-sodium sulfate solution (pH3) and a small amount of diatomite, oscillate, stand, delaminate, and accurately suck 1.5ml of the upper organic phase into another dry test tube. Before testing, the extractant was removed under N2 protection, and the residue was dissolved in 0.5ml of chloroform. According to the chromatographic conditions of this method, the content of various ginkgolic acids in ginkgo leaves is calculated by ginkgolic acid α3. The results are shown in the following figure. |
| use | used for content determination/identification/pharmacological experiments and other pharmacological effects: antioxidant, hypolipidemic; Anti-inflammatory |
Last Update：2024-04-09 15:16:48
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