Nerylacetone

Base Information

• Chemical Name: Nerylacetone
• CAS No.: 3879-26-3
• Molecular Formula: C13H22 O
• Molecular Weight: 194.317
• Hs Code.: 2914190090
• European Community (EC) Number: 626-253-2
• UNII: KZ9PY9FK2P
• Nikkaji Number: J133.547B
• Wikidata: Q67879718
• Metabolomics Workbench ID: 45148
• Mol file: 3879-26-3.mol

Synonyms:nerylacetone

Chemical Property of Nerylacetone

Chemical Property:

• Refractive Index: n20/D 1.467
• Boiling Point: 250-255 °C
• PSA: 17.07000
• Density: 0.868 g/mL at 20 °C(lit.)
• LogP: 4.04830
• Storage Temp.: 2-8°C
• 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% ^*data from raw suppliers

NERYLACETONE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C\CCC(=O)C)/C)C
• Uses: Nerylacetone is an intermediate in the synthesis of cis-Nerolidol (N390125), one of the main component in the essential oils from fresh aerial parts of Thymus ciliatus (Lamiaceae). Also, it is a terpene that displays high potency on the contractility of cardiac muscle in guinea pig left atrium. A potential and effective treatment for malaria.

Technology Process of Nerylacetone

There total 6 articles about Nerylacetone 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:

3,7-Dimethylocta-1,6-dien-3-yl acetoacetate (25456-03-5) → (Z)-nerylacetone (3879-26-3) + trans geranyl acetone (3796-70-1)

Guidance literature:

With palladium diacetate; sodium hydride; triphenylphosphine; In tert-butyl alcohol; at 50 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)77444-2

Reference yield:

(E)-2-Acetyl-5,9-dimethyl-deca-4,8-dienoic acid → (Z)-nerylacetone (3879-26-3) + trans geranyl acetone (3796-70-1)

Guidance literature:

In tetrachloromethane; at 77 ℃; for 1h; Yields of byproduct given;

DOI:10.1021/jo00178a036

Reference yield:

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + ethyl acetoacetate (141-97-9) → (Z)-nerylacetone (3879-26-3) + trans geranyl acetone (3796-70-1)

Guidance literature:

With aluminum isopropoxide;

DOI:10.1021/jo01363a021

upstream raw materials:

4-methyleneoxetan-2-one

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

ethyl acetoacetate

3,7-Dimethylocta-1,6-dien-3-yl acetoacetate

Downstream raw materials:

cis-nerolidol

methyl (2E,6Z)-farnesoate

ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate

ethyl 3,7,11-trimethyl-2ξ,6Z,10-dodecatrienoate