GEFRNATE
gefarnate
CAS: 51-77-4
Molecular Formula: C27H44O2
GEFRNATE - Names and Identifiers
| Name | gefarnate |
| Synonyms | Arsanate GEFRNATE Gefarnyl gefarnate Gifarnate Geranyl farnesylacetate geranyl 5,9,13-trimethyltetradeca-4,8,12-trienoate [(2E)-3,7-Dimethylocta-2,6-dienyl] (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoate (4E,8E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid (E)-3,7-dimethyl-2,6-octadienyl (2E)-3,7-dimethylocta-2,6-dien-1-yl (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoate 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester, (4E,8E)- |
| CAS | 51-77-4 |
| EINECS | 200-121-0 |
| InChI | InChI=1/C27H44O2/c1-22(2)12-8-14-24(5)16-10-17-25(6)18-11-19-27(28)29-21-20-26(7)15-9-13-23(3)4/h12-13,16,18,20H,8-11,14-15,17,19,21H2,1-7H3/b24-16+,25-18+,26-20+ |
GEFRNATE - Physico-chemical Properties
| Molecular Formula | C27H44O2 |
| Molar Mass | 400.64 |
| Density | 1.0044 (rough estimate) |
| Melting Point | 25°C |
| Boling Point | bp0.05 165-168° |
| Flash Point | 93.4°C |
| Vapor Presure | 1.5E-09mmHg at 25°C |
| Storage Condition | 2-8°C |
| Refractive Index | nD20 1.4900 |
| In vitro study | Gefarnate (0.001, 0.01, or 0.1 mg/mL) increases mucin-like glycoprotein secretion in a dose-dependent fashion, but the difference from the control is significant only at the concentration of 0.1 mg/mL. Gefarnate specifically stimulates the mucin-like glycoprotein secretion. |
GEFRNATE - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | gefalate is mainly used to treat acute and chronic gastritis, gastric and duodenal ulcers. it has the functions of accelerating metabolism, regulating gastrointestinal function and gastric acid secretion, strengthening mucosal protection, and is widely used in clinical practice. the study of its synthetic route has very important social significance. According to the current literature and the analysis of domestic and foreign patents, the use of orange flower tertiary alcohol as raw material to obtain farnyl acetate (ethyl ester), hydrolysis to obtain farnyl acetic acid, and then esterification to obtain farnyl acetate geraniol. The route is safe and environmentally friendly, uses easily available raw materials, avoids harsh processes, is friendly to equipment and the environment, and is suitable for industrial scale-up production. It is a crucial step to obtain the intermediate farnyl acetic acid with high purity. |
| Introduction | The chemical name of gifarate is 5,9,13-trimethyl -4,8,12-tetramethylene-3', 7 '-Dimethyl -2',6 '-octadienol ester. According to the analysis of the synthetic route of gifarate, the 2 '-position and 8-position double bonds in the chemical structure of gifarate are in the E configuration, while the 4-position double bonds are co-existing in the Z configuration and the E configuration. However, due to the undisclosed quality standard of gifarate, it is necessary to clarify the ratio of 4Z and 4E configurations in gifarate drugs, it provides method basis and reference for the imitation research of chemical drugs and the quality control of drugs. |
| Synthetic route | The drug standard of gifarate has been listed in the Japanese Pharmacopoeia, but there is no report on the inspection of related substances. In the research on the synthesis process of compound 1, it is found that its synthetic intermediates, by-products and other related substances will affect the product quality. According to the process route of compound 1 in the literature (as shown below) , 3 related substances have been synthesized, namely (3E,6E) -3,7,11-trimethyl -1,3,6,10-dodec-tetraene (A), (4E,8E) -Faroxyl Ester (B) and (4Z,8E) -Faroxyl Ester (C) have laid a foundation for process research, quality research and quality standard formulation. related substance a is a synthesis process impurity, in the preparation process of formyl methyl acetate by trans nerolol (2) in n-butyric acid catalyzed direct dehydration formation, the reaction formula is as follows. substance B is also an impurity in the synthesis process, which is formed by condensation of (4E,8E) -faunyl acetic acid (5) and nerol with low content in geraniol raw materials in the preparation process of gifarate products. the reaction formula: substance c is also an impurity in the synthesis process, in the preparation process of gifarate products, it is formed by the condensation of (4Z,8E) -Farinyl acetic acid (6) and the isomer nerol of geraniol. The reaction formula is shown below. |
| biological activity | Gefarnate is a drug for studying gastritis and gastric ulcer, and is currently also used for the study of dry eye. |
Last Update：2024-04-09 20:49:11
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View History
GEFRNATE
3,6-二硼酸频那醇酯-9H-咔唑
对苯二酚二羟乙基醚
Poly(oxy-1,2-ethanediyl), .alpha.-hydro-.omega.-hydroxy-, (Z)-9-octadecenoate
246876-15-3
碘代硫代乙酰胆碱
Porcn-IN-1
Heptasaccharide Glc4Xyl3
2-(Chloromethyl)-3,5-dimethylpyridine Hydrochloride
2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-N-(3-([3-(TRIFLUOROMETHYL)BENZYL]OXY)-2-THIENYL)-1-HYDRAZINECARBOXAMIDE
3,6-二硼酸频那醇酯-9H-咔唑
对苯二酚二羟乙基醚
Poly(oxy-1,2-ethanediyl), .alpha.-hydro-.omega.-hydroxy-, (Z)-9-octadecenoate
246876-15-3
碘代硫代乙酰胆碱
Porcn-IN-1
Heptasaccharide Glc4Xyl3
2-(Chloromethyl)-3,5-dimethylpyridine Hydrochloride
2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-N-(3-([3-(TRIFLUOROMETHYL)BENZYL]OXY)-2-THIENYL)-1-HYDRAZINECARBOXAMIDE