Teprenone

Base Information

• Chemical Name: Teprenone
• CAS No.: 3796-63-2
• Molecular Formula: C₂₃H₃₈O
• Molecular Weight: 330.554
• European Community (EC) Number: 614-276-0
• UNII: 57B67OXM8F
• ChEMBL ID: CHEMBL79686
• DSSTox Substance ID: DTXSID901166719
• Metabolomics Workbench ID: 70545
• NCI Thesaurus Code: C66587
• Nikkaji Number: J24.196B,J22.189I
• Wikidata: Q7701388
• Wikipedia: Teprenone
• Mol file: 3796-63-2.mol

Synonyms:6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one;geranyl-geranyl-acetone;geranylgeranylacetone;geranylgeranylacetone, (E,E,E)-isomer;geranylgeranylacetone, (Z,E,E)-isomer;teprenon;teprenone;tetraprenyl acetone;tetraprenylacetone

Chemical Property of Teprenone

Chemical Property:

• Vapor Pressure: 7.03E-08mmHg at 25°C
• Boiling Point: 442.2°Cat760mmHg
• Flash Point: 168°C
• PSA: 34.14000
• Density: 0.872g/cm³
• LogP: 15.00260
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 330.292265831
• Heavy Atom Count: 24
• Complexity: 482

Purity/Quality:

95% ^*data from raw suppliers

(5E,9E,13E)-Teprenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CCCC(=O)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CCC(=O)C)/C)/C)/C)C
• Recent ClinicalTrials: Evaluation of GeranylGeranylAcetone in Heart Failure With Preserved Ejection Fraction
• Recent EU Clinical Trials: Evaluation of GeranylGeranylAcetone in heart failure with preserved ejection fraction
• Recent NIPH Clinical Trials: An exploratory study for therapeutic effects of geranylgeranylacetone on heart failure
• Uses: (5E,9E,13E)-Teprenone is an isomer of Teprenone (T103500), An anti-ulcerative. Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Reports indicate that Teprenone protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression.

Technology Process of Teprenone

There total 21 articles about Teprenone 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:

5E,9E,13E-geranylgeranyl acetone 2,2-ethylenedioxyketal → (E,E,E)-geranylgeranylacetone (3796-63-2,3796-64-3,3796-65-4,3796-66-5,3796-67-6,3879-23-0,3879-24-1,3879-25-2,6809-52-5)

Guidance literature:

With phosphoric acid; In acetone;

DOI:10.1021/ja01052a081 DOI:10.1021/jo00824a023

Reference yield:

Farnesol (106-28-5) → (E,E,E)-geranylgeranylacetone (3796-63-2,3796-64-3,3796-65-4,3796-66-5,3796-67-6,3879-23-0,3879-24-1,3879-25-2,6809-52-5)

Guidance literature:

Multi-step reaction with 6 steps

1: phosphorus tribromide

2: sodium / ethanol

3: 288 mg

4: lithium aluminium hydride

5: phosphorus tribromide

6: sodium / ethanol

With lithium aluminium tetrahydride; sodium; phosphorus tribromide; In ethanol;

Reference yield:

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) → (E,E,E)-geranylgeranylacetone (3796-63-2,3796-64-3,3796-65-4,3796-66-5,3796-67-6,3879-23-0,3879-24-1,3879-25-2,6809-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 288 mg

2: lithium aluminium hydride

3: phosphorus tribromide

4: sodium / ethanol

With lithium aluminium tetrahydride; sodium; phosphorus tribromide; In ethanol;

upstream raw materials:

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

sodium acetylide

(4E,8E,12E)-ethyl 2-acetyl-5,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenoate

(6E,10E)-geranyllinalool

Downstream raw materials:

geranylfarnesol

(E,E,E,E)-geranylfarnesoic acid

Refernces

• 1、 Vlad, P. F.,Ungur, N. D.,Hung, Nguyen Van. "STRUCTURALLY SELECTIVE STEREOSPECIFIC CYCLIZATION OF E,E,E,E-GERANYLFARNESOL AND ITS ACETATE BY FLUOROSULFONIC ACID". . p. 651. Retrieved 2007/10/02.
• 2、 Dare,Entwistle,Johnstone. "Constituents of cigarette smoke. X. Evidence for 1,5-hydrogen transfer in the formation of non-conjugated isoprenoid polyolefins during pyrolysis.". . p. 977 - 980. Retrieved 2007/10/05.