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

Description

Nerylacetone is a terpene compound that serves as an intermediate in the synthesis of cis-Nerolidol (N390125), a key component found in the essential oils of Thymus ciliatus (Lamiaceae). It is known for its high potency in enhancing the contractility of cardiac muscle in guinea pig left atrium and has potential as an effective treatment for malaria.

Uses

Used in Pharmaceutical Industry:
Nerylacetone is used as an intermediate in the synthesis of cis-Nerolidol for its various pharmaceutical applications, including its potential as a treatment for malaria.
Used in Essential Oils Industry:
Nerylacetone is used as a component in the production of essential oils derived from the fresh aerial parts of Thymus ciliatus (Lamiaceae), contributing to their unique properties and uses.
Used in Cardiology Research:
Nerylacetone is used as a research compound for studying its effects on the contractility of cardiac muscle in guinea pig left atrium, which may lead to advancements in cardiology and the development of new treatments for heart-related conditions.

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 
• 25456-03-5 3,7-Dimethylocta-1,6-dien-3-yl acetoacetate 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 4176-79-8 methyl (2E,6Z)-farnesoate 
• 19954-66-6 ethyl 3,7,11-trimethyl-2ξ,6Z,10-dodecatrienoate 
• 20085-73-8 ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 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 
• 159826-46-7 6,10-dimethyl-3-phenylthioundeca-5Z,9-dien-2-one 
• 4176-78-7 methyl (2Z,6Z)-farnesenate 
• 863-61-6 2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2t,6t,10c,14-tetraenyl)-[1,4]naphthoquinone 
• 156848-67-8 C₂₂H₂₉BrO₃ 

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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