51-77-4

Basic information

• Product Name: Gefarnate
• Synonyms: [(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;Terpanil;(4E,8E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid (7-methyl-3-methylene-6-octenyl) ester;γ-Geraniol farnesylacetate;3,7-Dimethylocta-2,6-dien-1-yl 5,9,13-trimethyltetradeca-4,8,12-trienoate
• CAS NO: 51-77-4
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.63706
• EINECS: 200-121-0
• Mol File: 51-77-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 25°C
• Boiling Point: bp0.05 165-168°
• Flash Point: 93.4 °C
• Appearance: /
• Density: 1.0044 (rough estimate)
• Vapor Pressure: 1.5E-09mmHg at 25°C
• Refractive Index: nD20 1.4900
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Gefarnate(CAS DataBase Reference)
• NIST Chemistry Reference: Gefarnate(51-77-4)
• EPA Substance Registry System: Gefarnate(51-77-4)

Safety Data

• Hazardous Substances Data: 51-77-4(Hazardous Substances Data)

Usage

Uses

Gefarnate is a synthetic isoprenoid that is used to treat chronic gastric and duodenic ulcers. Gerfarnate is also used for gastric ulcer prophylaxis.

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

Relevant articles and documents

IMPROVED METHOD FOR THE ISOLATION OF GERANYL ESTERS OF (4E/Z,8E)- AND (4E/Z,8Z)-FARNESYLACETIC ACID

-

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.