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Gefarnate

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CAS:51-77-4
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Gefarnate manufacturers

  • Gefarnate
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  • $56.00 / 200mg
  • 2026-02-01
  • CAS:51-77-4
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  • Purity: 98.36%
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  • Gefarnate
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  • 2021-07-02
  • CAS:51-77-4
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  • Gefarnate
  • Gefarnate pictures
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  • 2019-07-06
  • CAS: 51-77-4
  • Min. Order: 1KG
  • Purity: 99%
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Gefarnate Basic information
Product Name:Gefarnate
Synonyms:Gifarnate;Geranyl farnesylacetate;4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester, (4E,8E)-;GEFRNATE;[(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;Arsanate;Gefarnyl
CAS:51-77-4
MF:C27H44O2
MW:400.64
EINECS:200-121-0
Product Categories:
Mol File:51-77-4.mol
Gefarnate Structure
Gefarnate Chemical Properties
Melting point 25°C
Boiling point bp0.05 165-168°
density 1.0044 (rough estimate)
refractive index nD20 1.4900
storage temp. 2-8°C
solubility DMSO:31.25(Max Conc. mg/mL);78.0(Max Conc. mM)
form Oil
color Clear Colourless
Stability:Light Sensitive
InChI1S/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+
InChIKeyZPACYDRSPFRDHO-ROBAGEODSA-N
SMILESCC(C)=CCC/C(C)=C/COC(CC/C=C(CC/C=C(CCC=C(C)C)\C)\C)=O
EPA Substance Registry System4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester, (4E,8E)- (51-77-4)
Safety Information
WGK Germany WGK 3
TSCA TSCA listed
Storage Class10 - Combustible liquids
MSDS Information
Gefarnate Usage And Synthesis
UsesGefarnate is a synthetic isoprenoid that is used to treat chronic gastric and duodenic ulcers. Gerfarnate is also used for gastric ulcer prophylaxis.
DefinitionChEBI: Gefarnate is an organic molecular entity.
Biological ActivityGefarnate is an anti-ulcer drug th at stimulates gastric mucin secretion. Also gefarnate increase secretion of mucin-like glycoprotein in rabbit conjunctival tissue. It appears to be effective in animal dry-eye models. It is approved in Japan, where it is used to tre at gastritis and gastric ulcer. Gefarnate is structurally similar to anti-ulcer drug teprenone (geranyl farnesylacetate), which induces expression of HSP70, HSPB8, and HSPB1.
Synthesis
Geraniol

106-24-1

(4E,8E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid

6040-06-8

Gefarnate

51-77-4

The general procedure for the synthesis of (4E,8E)-(E)-3,7-dimethylocta-2,6-dien-1-yl 5,9,13-trimethyltetradeca-4,8,12-trienoate from geraniol and (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoate was performed as follows: 10.3 g farnesyl acetic acid, 15.0 g g geraniol, 25.0 mL xylene and 0.43 g hydroquinone were mixed and refluxed for about 10 hours. The progress of the reaction was monitored during the reaction using thin layer chromatography (TLC with a spreader ratio of petroleum ether/ethyl acetate = 25:1) and the complete reaction of farnesylacetic acid was confirmed by TLC (spreader ratio of petroleum ether/ethyl acetate = 5:1). Upon completion of the reaction, an orange-yellow transparent mixed solution was obtained, which was slightly cooled and xylene was removed by distillation under reduced pressure. The residue was extracted 2-3 times with hexane and 1% (w/w) sodium hydroxide solution, the organic phase was separated, dried and some of the solvent was removed by rotary evaporation. The residue was dried over anhydrous calcium chloride and the mixture was stirred overnight at room temperature and the filtrate was collected by filtration. The filtrate was concentrated to give the crude product of gefarnate ester. The crude product was purified by reduced pressure distillation and the 186-200 °C fraction was collected to give the pure gefarnate ester product.

References[1] Patent: CN103012140, 2016, B. Location in patent: Paragraph 0071; 0074; 0093
Tag:Gefarnate(51-77-4) Related Product Information
Dimethicone N,N-Dimethylacetamide Dimethyl sulfoxide Dichlorodimethylsilane N,N-Dimethylformamide N,N-Dimethylaniline Dimethyl sulfone Poly(dimethylsiloxane) Geranyl acetate 2-Dimethylaminoethanol GERANYL BUTYRATE Geraniol GERANYL PROPIONATE ETHYL TRANS-4-OCTENOATE TRANS-2-HEXENYL BUTYRATE farnesylacetic acid Gefarnate 3,7-DECADIENE

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