5,9-Dimethyl-4,8-decadienoic acid

Base Information

• Chemical Name: 5,9-Dimethyl-4,8-decadienoic acid
• CAS No.: 5579-63-5
• Molecular Formula: C12H20O2
• Molecular Weight: 196.29
• European Community (EC) Number: 254-951-3
• DSSTox Substance ID: DTXSID901339663
• Nikkaji Number: J37.637J,J332.438I
• Mol file: 5579-63-5.mol

Synonyms:5,9-Dimethyl-4,8-decadienoic acid;geranylacetic acid;5579-63-5;40518-76-1;4,8-Decadienoic acid, 5,9-dimethyl-, (4E)-;EINECS 254-951-3;(4E)-5,9-dimethyldeca-4,8-dienoic acid;SCHEMBL458219;SCHEMBL458220;DTXSID901339663

Chemical Property of 5,9-Dimethyl-4,8-decadienoic acid

Chemical Property:

• Melting Point: -1.5 °C
• Boiling Point: 179 °C(Press: 19 Torr)
• PKA: 4.61±0.10(Predicted)
• PSA: 37.30000
• Density: 0.938 g/cm3(Temp: 21 °C)
• LogP: 3.54390
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CCC(=O)O)/C)C

Technology Process of 5,9-Dimethyl-4,8-decadienoic acid

There total 15 articles about 5,9-Dimethyl-4,8-decadienoic acid 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: 97.0%

ethyl (E)-5,9-dimethyl-4,8-decadienoate (19894-83-8) → geranylacetic acid (5579-63-5)

Guidance literature:

With sodium hydroxide; In ethanol; for 8h; Heating;

DOI:10.1016/S0968-0896(00)00212-1

Reference yield: 84.0%

2-(3,7-diemthylocta-2E,6-dienyl)malonic acid (62088-06-6) → geranylacetic acid (5579-63-5)

Guidance literature:

With pyridine; In water; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2017.02.066

Reference yield: 77.0%

diethyl [(2E)-3,7-dimethylocta-2,6-dienyl]malonate (19894-79-2) → geranylacetic acid (5579-63-5)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h; Heating;

DOI:10.1021/ja00378a023

upstream raw materials:

methyl magnesium iodide

9-methyl-5-oxo-dec-8-enoic acid

homogeranyl bromide

carbon dioxide

Downstream raw materials:

<(E)-5,9-Dimethyl-4,8-decadienyl>triphenylphosphonium iodide

(E)-5,9-Dimethyl-deca-4,8-dienoic acid (4-isopropyl-phenyl)-amide

(1S*,6R*)-1,7,7-Trimethyl-2-oxabicyclo<4.4.0>decan-3-one

trans-5,5,9-trimethyl-1-oxabicyclo<4.4.0>decan-2-one

Refernces

• 1、 Wills, Veronica S.,Metzger, Joseph I.,Allen, Cheryl,Varney, Michelle L.,Wiemer, David F.,Holstein, Sarah A.. "Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase". supporting information. p. 2437 - 2444. Retrieved 2017/04/03.
• 2、 Nakano, Shin-Ichi,Ohashi, Shumi,Hoshino, Tsutomu. "Squalene-hopene cyclase: Insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C(7) or C(11)". . p. 2012 - 2022. Retrieved 2007/10/03.