Gefarnate

Base Information

• Chemical Name: Gefarnate
• CAS No.: 51-77-4
• Deprecated CAS: 30462-47-6
• Molecular Formula: C27H44O2
• Molecular Weight: 400.645
• European Community (EC) Number: 200-121-0
• UNII: 1ISE2Y6ULA
• ChEMBL ID: CHEMBL2105085
• DSSTox Substance ID: DTXSID0048636
• Metabolomics Workbench ID: 153132
• NCI Thesaurus Code: C73187
• Nikkaji Number: J445.674B,J1.364A,J318.296G
• NSC Number: 138947
• Wikidata: Q5530013
• Wikipedia: Gefarnate
• Mol file: 51-77-4.mol

Synonyms:Farnesylacetate, Geranyl;Gefarnate;Gefarnil;Gepharnate;Geranyl Farnesylacetate;Ulco

Chemical Property of Gefarnate

Chemical Property:

• Vapor Pressure: 1.5E-09mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: 1.489
• Boiling Point: 484.7 °C at 760 mmHg
• Flash Point: 93.4 °C
• PSA: 26.30000
• Density: 0.9 g/cm³
• LogP: 8.42170
• Storage Temp.: 2-8°C
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 619

Purity/Quality:

99% ^*data from raw suppliers

Gefarnate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=O)OCC=C(C)CCC=C(C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CCC(=O)OC/C=C(\C)/CCC=C(C)C)/C)/C)C
• Recent ClinicalTrials: Lipid-lowering Effects of Gefarnate in Statin-treated Coronary Heart Disease Patients With Residual Hypertriglyceridemia
• Recent NIPH Clinical Trials: Prophylactic efficacy of Proton Pump Inhibitor on Recurrence of Peptic Ulcer in Patients continuously treated with Low-dose Aspirin-Randomized, Multi-center, single-blinded, parallel-group, comparative study-
• Uses: Gefarnate is a synthetic isoprenoid that is used to treat chronic gastric and duodenic ulcers. Gerfarnate is also used for gastric ulcer prophylaxis.

Technology Process of Gefarnate

There total 10 articles about Gefarnate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

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

Guidance literature:

With hydroquinone; In 5,5-dimethyl-1,3-cyclohexadiene; for 10h; Reflux;

Reference yield: 73.0%

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

Guidance literature:

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

DOI:10.1055/s-1981-29599

Reference yield:

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

Guidance literature:

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

With pyridine; disodium hydrogenphosphate; sodium amalgam; sodium hydride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1055/s-1981-29599

upstream raw materials:

Geraniol

(4E/Z,8E)-Farnesylmalonic diethyl ester

(E)-Geranyl α-(E,E)-farnesyl-α-p-tolylsulfonylacetate

farnesyl bromide

Refernces

• 1、 -. "Method for preparing characterized". Paragraph 0071; 0074; 0093. . Retrieved 2017/01/09.
• 2、 Sato,Inoue,Sakamoto. "Synthesis of polyprenylacetones and -acetates; application to a new synthesis of gefarnate". . p. 796 - 798. Retrieved 2007/10/02.