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

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

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

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

Downstream Products

• 20085-73-8 ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 159826-46-7 6,10-dimethyl-3-phenylthioundeca-5Z,9-dien-2-one 
• 4176-78-7 methyl (2Z,6Z)-farnesenate 
• 4176-79-8 methyl (2E,6Z)-farnesoate 
• 6819-38-1 neryl isopropanol 
• 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 
• 3239-37-0 (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate 
• 39721-65-8 (R)-(+)-α-dihydroionone 
• 670-24-6 (-)-β-ambrinol 
• 140386-30-7 (+)-α-ambrinol 
• 1604-35-9 (7R)-3,7,11-trimethyldodec-1-yn-3-ol 

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.

Isoprenoid Chain Elongations by Claisen Rearrangements Using Acetals as Precursors of Vinyl Ethers

Claisen rearrangements of allyl vinyl ethers, formed in situ by the acid catalyzed reaction of dimethyl acetals of acetaldehyde, acetone and isopropenyl methyl ketone with different types of allylic alcohols, have been compared.The primary, secondary and tertiary allylic alcohols used in the investigation were selected to serve as models for isoprenoid synthesis.The basis for two feasible methods that can be iterated to create isoprenoid chains has been investigated.

Allylic Carbonates. Efficient Allylating Agents of Carbonucleophiles in Palladium-Catalyzed Reactions under Neutral Conditions

Allylation of β-keto esters or malonates was carried out in good yields under neutral conditions by using allylic carbonates in the presence of palladium-phospine catalyst.Although simple ketones, esters, nitriles, and sulfones hardly react with allylic carbonates, α-alkenyl or α-aryl ketones, esters, nitriles, and sulfones were also allylated by using palladium-bis(diphenylphosphino)ethane catalyst under neutral conditions.

PALLADIUM-CATALYZED REARRANGEMENT OF ALLYLIC ESTERS OF ACETOACETIC ACID TO GIVE γ,δ-UNSATURATED METHYL KETONES

Various allylic esters of acetoacetic acid undergo rearrangement to give γ,δ-unsaturated methyl ketones in high yields with elimination of carbon dioxide under mild conditions in the presence of catalytic amounts of Pd(OAc)2 and PPh3.