(3E,7Z)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one

Base Information

• Chemical Name: (3E,7Z)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
• CAS No.: 6902-91-6
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• Hs Code.: 29142990
• European Community (EC) Number: 834-535-3
• Wikipedia: Germacrone
• Mol file: 6902-91-6.mol

Synonyms:germacron;germacrone

Chemical Property of (3E,7Z)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one

Chemical Property:

• Vapor Pressure: 0.000168mmHg at 25°C
• Melting Point: 55-58 °C
• Refractive Index: 1.485
• Boiling Point: 330.274 °C at 760 mmHg
• Flash Point: 148.419 °C
• PSA: 17.07000
• Density: 0.916 g/cm³
• LogP: 4.35850
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 363

Purity/Quality:

98%,99%, ^*data from raw suppliers

Germacrone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(=C(C)C)C(=O)CC(=CCC1)C
• Isomeric SMILES: C/C/1=C/CC(=C(C)C)C(=O)C/C(=C/CC1)/C
• Description: Germacrone is a sesquiterpene that has been found in gingeraceae plants and has diverse biological activities. It inhibits pseudorabies virus (PRV) replication in Vero cells when used at concentrations ranging from 10 to 150 μM. Germacrone (50-250 μM) enhances cytotoxicity and apoptosis induced by doxorubicin in doxorubicin-resistant MCF-7/adr cells. In vivo, germacrone (5, 10, and 20 mg/kg) reduces body weight gain, visceral fat pad weight, serum insulin and plasma glucose levels, and hepatic lipid levels in a mouse model of high-fat diet-induced obesity. It decreases brain malondialdehyde (MDA) levels and activity of superoxide dismutase (SOD) and glutathione peroxidase (GPX), as well as reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).
• Uses: Germacrone is an antiviral isolate of Geranium macrorrhizum which inhibits and prevents early stage influenza virus infection. It also inhibits the proliferation of glioma cells by promoting apoptosis.

Technology Process of (3E,7Z)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one

There total 14 articles about (3E,7Z)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-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:

8-hydroxygeranyl acetate (37905-03-6) → germacrone (6902-91-6)

Guidance literature:

Multi-step reaction with 13 steps

2: 65 percent / triphenylphosphine / palladium acetate / tetrahydrofuran / 5 h / Heating

3: 95 percent / sodium hydride / diethyl ether / 0 °C

4: 70 percent / diethyl ether / -10 °C

5: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating

6: diisobutylaluminium hydride / tetrahydrofuran / -40 °C

7: manganese dioxide / hexane / Ambient temperature

8: KCN, 18-crown-6 / 1 h / 0 °C

9: trimethylbenzylammonium fluoride / tetrahydrofuran; H₂O / 0 °C

11: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C

12: p-toluenesulfonic acid / methanol / 1 h / 0 °C

13: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h

With tetrachloromethane; potassium cyanide; manganese(IV) oxide; sodium hydroxide; 18-crown-6 ether; sodium hexamethyldisilazane; trimethyl(benzyl)ammonium fluoride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; hexane; water;

DOI:10.1016/S0040-4039(00)86020-7

Reference yield:

Acetic acid (2E,6E)-8-(1-ethoxy-ethoxy)-3,7-dimethyl-octa-2,6-dienyl ester (87064-43-5) → germacrone (6902-91-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 65 percent / triphenylphosphine / palladium acetate / tetrahydrofuran / 5 h / Heating

2: 95 percent / sodium hydride / diethyl ether / 0 °C

3: 70 percent / diethyl ether / -10 °C

4: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating

5: diisobutylaluminium hydride / tetrahydrofuran / -40 °C

6: manganese dioxide / hexane / Ambient temperature

7: KCN, 18-crown-6 / 1 h / 0 °C

8: trimethylbenzylammonium fluoride / tetrahydrofuran; H₂O / 0 °C

10: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C

11: p-toluenesulfonic acid / methanol / 1 h / 0 °C

12: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h

With tetrachloromethane; potassium cyanide; manganese(IV) oxide; sodium hydroxide; 18-crown-6 ether; sodium hexamethyldisilazane; trimethyl(benzyl)ammonium fluoride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; hexane; water;

DOI:10.1016/S0040-4039(00)86020-7

Reference yield:

(3E,7E)-1-Hydroxy-10-isopropylidene-3,7-dimethyl-cyclodeca-3,7-dienecarbonitrile (87920-50-1) → germacrone (6902-91-6)

Guidance literature:

With sodium hydroxide; In diethyl ether; for 0.333333h; Yield given;

DOI:10.1016/S0040-4039(00)86020-7

upstream raw materials:

(3E,7E)-1-Hydroxy-10-isopropylidene-3,7-dimethyl-cyclodeca-3,7-dienecarbonitrile

8-hydroxygeranyl acetate

(4E,8E)-10-Chloro-2-isopropylidene-5,9-dimethyl-deca-4,8-dien-1-ol

(4E,8E)-10-Chloro-2-isopropylidene-5,9-dimethyl-deca-4,8-dienal

Downstream raw materials:

germacrone-4,5-epoxide

germacrone-1,10-epoxide

isogermacrone <(2Z,7E)-3,7-dimethyl-10-(1-methylethylidene)-2,7-cyclodecadien-1-one>

(+/-)-1,10-Dimethyl-Δ¹⁽⁹⁾-octalin

Refernces