51-77-4

Usage

Uses

Used in Pharmaceutical Industry:
Gefarnate is used as a therapeutic agent for treating chronic gastric and duodenic ulcers. Its anti-ulcerogenic properties help in reducing the severity and symptoms of these conditions, providing relief to patients suffering from such ailments.
Additionally, Gefarnate is used as a prophylactic agent for gastric ulcers. By preventing the development of gastric ulcers, it contributes to the overall well-being and health of individuals at risk of developing these conditions.

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+

Synthetic route

Geraniol (106-24-1) + (4E,8E,12E)-5,9,13-trimethyl-4,8,12-tetradecatrienoic acid (6040-06-8) → gefarnate (51-77-4)

Conditions	Yield
With hydroquinone In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Reflux;	99%

(E)-Geranyl α-(E,E)-farnesyl-α-p-tolylsulfonylacetate (80868-14-0) → gefarnate (51-77-4)

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In various solvent(s) for 25h; Ambient temperature;	73%

Geraniol (106-24-1) + (4E/Z,8E)-Farnesylmalonic diethyl ester (26732-80-9, 58456-68-1, 58456-69-2, 58456-70-5, 58456-71-6) → (4Z,8E)-Farnesylacetic acid geranyl ester (30462-48-7) + gefarnate (51-77-4)

Conditions	Yield
at 185 - 190℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Geraniol (106-24-1) → gefarnate (51-77-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / Pyridine / diethyl ether / 4 h / 1 - 3 °C 2: 88 percent / dimethylformamide / 3 h / 55 - 60 °C 3: 1.) Sodium hydride / DMF 1.) r.t., 1.5 h, 2.) 30 h 4: 73 percent / Na/Hg, Na2HPO4 / various solvent(s) / 25 h / Ambient temperature View Scheme

farnesyl bromide (24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7) → gefarnate (51-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Sodium hydride / DMF 1.) r.t., 1.5 h, 2.) 30 h 2: 73 percent / Na/Hg, Na2HPO4 / various solvent(s) / 25 h / Ambient temperature View Scheme

(E)-Geranyl chloroacetate (60758-60-3) → gefarnate (51-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / dimethylformamide / 3 h / 55 - 60 °C 2: 1.) Sodium hydride / DMF 1.) r.t., 1.5 h, 2.) 30 h 3: 73 percent / Na/Hg, Na2HPO4 / various solvent(s) / 25 h / Ambient temperature View Scheme

(E)-Geranyl p-toluenesufonylacetate (80868-13-9) → gefarnate (51-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Sodium hydride / DMF 1.) r.t., 1.5 h, 2.) 30 h 2: 73 percent / Na/Hg, Na2HPO4 / various solvent(s) / 25 h / Ambient temperature View Scheme

Upstream product

• 106-24-1 Geraniol 
• 26732-80-9 (4E/Z,8E)-Farnesylmalonic diethyl ester 
• 80868-14-0 (E)-Geranyl α-(E,E)-farnesyl-α-p-tolylsulfonylacetate 
• 24163-93-7 farnesyl bromide 
• 60758-60-3 (E)-Geranyl chloroacetate 
• 80868-13-9 (E)-Geranyl p-toluenesufonylacetate 
• 6040-06-8 (4E,8E,12E)-5,9,13-trimethyl-4,8,12-tetradecatrienoic acid 
• 22128-24-1 5,9,13-Trimethyl-4,8,12-tetradecatrienoylchlorid 
• 23224-49-9 5,9,13-trimethyl-tetradeca-4,8,12-trienoic acid 

Relevant academic research and scientific papers

Method for preparing characterized

The invention provides a preparation method of gefarnate. The preparation method is characterized by comprising the following steps: conducting phosphorylation reaction on bromobutyric acid ethyl ester and triphenylphosphine to obtain phosphorus ylide solution, conducting whittig reaction to the phosphorus ylide solution and geranylacetone to obtain farnesyl ethyl acetate; adding the farnesyl ethyl acetate into sodium hydroxide and N,N-dimethylformamide so as to conduct acidification reaction to obtain farnesyl acetic acid; and adding geraniol, dimethylbenzene and a polymerization inhibitor into farnesyl acetic acid for conducting heating reflux and vacuum concentration, and collecting fraction at 186-200 DEG C to obtain gefarnate. According to the method, the technical problems that the gefarnate obtained in the prior art is long in synthetic route, low in yield, low in yield purity, complicated in after-treatment, and not applicable to industrial production can be solved.

Therapeutic preparations for peptic ulcers comprising aliphatic ketone derivative

A therapeutic preparation having excellent effect for peptic ulcers with low toxicity which comprises aliphatic ketone derivative of the general formula: STR1 wherein represents a saturated or unsaturated bond, R1 is hydrogen or a lower alkyl group, R2 is hydrogen atom, a lower alkyl group or a lower alkylcarbonyl group, R3 is an aliphatic hydrocarbon group of the general formula: STR2 WHEREIN L, M AND N ARE 0 OR 1, PROVIDED THAT L+M+N≥2; AND A, B, C, D, E AND F ARE HYDROGEN ATOM, OR THEY MAY FORM A BOND OF A--B, C--D OR E--F, PROVIDED THAT IF THE BOND IS A SATURATED BOND, THE A, B, C, D, E AND F REPRESENT ALL HYDROGEN ATOM.