Geranylacetone

Base Information

• Chemical Name: Geranylacetone
• CAS No.: 3796-70-1
• Deprecated CAS: 2381218-05-7
• Molecular Formula: C13H22O
• Molecular Weight: 194.317
• Hs Code.: 29141900
• European Community (EC) Number: 211-711-2,223-269-8
• NSC Number: 406679
• UNII: 9B7RY79U9Z
• DSSTox Substance ID: DTXSID4052053
• Nikkaji Number: J35.918A,J24.231D
• Wikipedia: Geranylacetone
• Wikidata: Q27135687
• Metabolomics Workbench ID: 5391
• Mol file: 3796-70-1.mol

Synonyms:geranyl acetone;geranylacetone;geranylacetone, (E)-isomer

Chemical Property of Geranylacetone

Chemical Property:

• Appearance/Colour: 26-37/39-36
• Vapor Pressure: 0.0157mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 256.038 °C at 760 mmHg
• Flash Point: 107.443 °C
• PSA: 17.07000
• Density: 0.856 g/cm³
• LogP: 4.04830
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 194.167065321
• Heavy Atom Count: 14
• Complexity: 230

Purity/Quality:

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

(E)-6,10-Dimethylundeca-5,9-dien-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=CCCC(=CCCC(=O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CCC(=O)C)/C)C
• Uses: (E)-6,10-Dimethylundeca-5,9-dien-2-one is diastereoselective used in preparation of Geranyl Acetone by Carroll reaction of linalool with Acetoacetate.

Technology Process of Geranylacetone

There total 50 articles about Geranylacetone 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: 95.0%

(E)-2-acetyl-5,9-dimethyldeca-4,8-dienoic acid ethyl ester (19894-78-1) → trans geranyl acetone (3796-70-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 3h; Reflux;

DOI:10.1055/s-0032-1317528

Reference yield: 93.0%

(E)-6,10-dimethyl-5,9-undecadien-2-ol (7733-91-7,53837-34-6) → trans geranyl acetone (3796-70-1)

Guidance literature:

With polystyrene-supported(cathecholato)oxoRe cat. act. by iPrOH; dimethyl sulfoxide; In toluene; for 4h; Heating; Dean-Stark apparatus;

DOI:10.1002/1522-2675(200210)85:10<3225::AID-HLCA3225>3.0.CO;2-H

Reference yield: 90.0%

(E)-6,10-Dimethyl-3-(toluene-4-sulfonyl)-undeca-5,9-dien-2-one (80868-08-2) → trans geranyl acetone (3796-70-1)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 2h;

DOI:10.1055/s-1981-29599

upstream raw materials:

4-methyleneoxetan-2-one

3,7-dimethylocta-1,6-dien-3-ol

geranyl chloride

sodium ethyl acetylacetate enolate

Downstream raw materials:

3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Farnesol

2,6-dimethyl-10-(p-tolyl)-2,6(E)-undecadiene

5-(E)-2,6,10-trimethyl-1,5,9-undecatriene

Refernces

• 1、 Wakabayashi,N. et al.. "". . p. 3253 - 3256. Retrieved 1969.
• 2、 -. "Synthesis method and method for synthesizing plant alcohol, isoplant alcohol and geranyl geraniol by using intermediate farnesylacetone (by machine translation)". Paragraph 0061; 0072; 0080-0081. . Retrieved 2020/07/21.
• 3、 Borra, Suresh,Kumar, Manoj,McNulty, James,Baidilov, Daler,Hudlicky, Tomas. "Chemoenzymatic Synthesis of the Antifungal Compound (–)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-Diene". supporting information. p. 77 - 79. Retrieved 2018/11/23.