3879-26-3

Basic information

• Product Name: NERYLACETONE
• Synonyms: (5Z)-6,10-Dimethyl-5,9-undecadien-2-one;5,9-Undecadien-2-one, 6,10-dimethyl-, (Z)-;NERYLACETONE;CIS-GERANYLACETONE;CIS-6,10-DIMETHYLUNDECA-5,9-DIEN-2-ONE;(5Z)-6,10-Dimethyl-5,9-undecadiene-2-one;(Z)-6,10-Dimethyl-5,9-undecadien-2-one;(5Z)-6,10-dimethylundeca-5,9-dien-2-one
• CAS NO: 3879-26-3
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.31
• Mol File: 3879-26-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 250-255 °C
• Appearance: /
• Density: 0.868 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.467
• Storage Temp.: 2-8°C
• CAS DataBase Reference: NERYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: NERYLACETONE(3879-26-3)
• EPA Substance Registry System: NERYLACETONE(3879-26-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3879-26-3(Hazardous Substances Data)

Usage

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.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 6870, 1975 DOI: 10.1021/ja00856a049The Journal of Organic Chemistry, 38, p. 4082, 1973 DOI: 10.1021/jo00987a035

Upstream product

• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 77-76-9 2,2-dimethoxy-propane 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 
• 25456-03-5 3,7-Dimethylocta-1,6-dien-3-yl acetoacetate 

Downstream Products

• 3790-78-1 cis-nerolidol 
• 4176-79-8 methyl (2E,6Z)-farnesoate 
• 20085-73-8 ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 3796-70-1 trans geranyl acetone 
• 20085-72-7 ethyl (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 6819-38-1 neryl isopropanol 
• 170081-81-9 rac-(Z)-9,10-dihydroxy-6,10-dimethylundec-5-en-2-one 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 31499-72-6 7,8-dihydro-α-ionone 
• 6136-74-9 (+/-)-2,5,5,8a-tetramethyl-cis-4a,5,6,7,8,8a-hexahydro-4H-chromene 
• 6136-74-9 (+/-)-2,5,5,8a-tetramethyl-trans-4a,5,6,7,8,8a-hexahydro-4H-chromene 
• 670-24-6 (-)-β-ambrinol 
• 140386-30-7 (+)-α-ambrinol 
• 3239-37-0 (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate 

Relevant articles and documents

Stereoselective Synthesis of (E)- and (Z)-γ,δ-Unsaturated Ketones Using trans-2-Phenylthiocyclobutyl Ketones

The reaction of 1-methoxymethyl-2-phenylthiocyclobutanes with phenylthiotrimethylsilane followed by hydrolysis gave (E)- and (Z)-γ,δ-unsaturated ketones with high stereoselectivity.The starting materials were easily prepared by the stereoselective addition of Grignard reagents to trans-2-phenylthiocyclobutyl ketones.

IMPROVED METHOD FOR THE ISOLATION OF GERANYL ESTERS OF (4E/Z,8E)- AND (4E/Z,8Z)-FARNESYLACETIC ACID

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The Ester Enolate Carroll Rearrangement

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