6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one

Base Information

• Chemical Name: 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one
• CAS No.: 6809-52-5
• Molecular Formula: C23H38O
• Molecular Weight: 330.554
• Hs Code.: 2914190090
• European Community (EC) Number: 614-276-0
• DSSTox Substance ID: DTXSID6048620
• ChEMBL ID: CHEMBL3183658
• Mol file: 6809-52-5.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 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one

Chemical Property:

• Vapor Pressure: 5.12E-08mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 442.2 °C at 760 mmHg
• Flash Point: 168 °C
• PSA: 17.07000
• Density: 0.872 g/cm³
• LogP: 7.89140
• Storage Temp.: ?20°C
• Solubility.: DMSO: >5mg/mL
• 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:

99% ^*data from raw suppliers

Teprenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CCCC(=O)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CCC(=CCCC(=O)C)C)/C)/C)C
• Description: Teprenone (geranylgeranylacetone) is an antiulcer agent whose synthesis was inspired by the gastric protecting properties of Coenzyme Q10. Teprenone is reported to act via enhancement of gastric mucosal glycoprotein secretion. Geranylgeranylacetone is an inducer of heat shock protein (Hsp) expression that has been shown to increase Hsp70 (also known as Hsp72 and HspA1A), Hsp22 (HspB8), Hsp27 (HspB1), Hsp90 (HspC), and Hsp105 (HspH1) levels in various cells and tissues. It is orally bioavailable and has diverse effects in vivo, including hepatoprotective, neuroprotective, and antiulcerative effects. The effects of geranylgeranylacetone on Hsp expression are more pronounced under stress conditions.
• Uses: An anti-ulcerative. Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spinal and bulbar muscular atrophy (cytoprotective and anti-inflammatory effects). Reports indicate that GGA protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression. Other studies have shown that GGA induces expression of HSPB8 and HSPB1 and reduces the formation of amyloid oligomers as well as insoluble aggregates in HSPB5 R120G TG mice. Geranylgeranylacetone has been used as an inducer of heat shock protein 70 (HSP70) to analyze its protective effects against cerebral ischemia/reperfusion (I/R).

Technology Process of 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one

There total 55 articles about 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one 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: 50.0%

(4E,8E,12E)-ethyl 2-acetyl-5,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenoate (71668-81-0) → 5E,9E,13E-geranylgeranyl acetone (6809-52-5)

Guidance literature:

With potassium hydroxide; In methanol; water; at 80 - 85 ℃; for 2h;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3,5-dibromo-4-(di-tert-butyl(nonaprenyloxy)silyloxy)benzoic acid (1033756-53-4) → farnesylfarnesylacetone (32304-17-9) + geranylfarnesylacetone (86541-61-9) + C22H36O2 (869878-11-5) + 10-hydroxy-4,8-dimethyldeca-4,8-dienal (87920-55-6) + methyl 3,5-dibromo-4-hydroxybenzoate (41727-47-3) + (4E,8E,12E)-14-hydroxy-4,8,12-trimethyltetradeca-4,8,12-trienal (87920-56-7) + 5E,9E,13E-geranylgeranyl acetone (6809-52-5)

Guidance literature:

3,5-dibromo-4-(di-tert-butyl(nonaprenyloxy)silyloxy)benzoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 23 ℃; for 0.5h;

With dihydrogen peroxide; In dichloromethane; at -78 - -20 ℃;

diazomethane; With tetrabutylammonium periodite; pyridine hydrogenfluoride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; Further stages;

DOI:10.1021/ja801899v

Reference yield:

C24H38O3 (1206897-24-6) → 5E,9E,13E-geranylgeranyl acetone (6809-52-5)

Guidance literature:

With aluminum isopropoxide; at 140 - 160 ℃;

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:

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

geranylfarnesol

2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4)

Refernces

• 1、 -. "Novel intermediate for synthesizing teprenone and application of novel intermediate". . . Retrieved 2019/04/17.
• 2、 -. "Process for synthesizing teprenone". . . Retrieved 2017/03/28.