54082-68-7

Basic information

• Product Name: 2,6,10-trimethylundeca-5,9-dienal
• Synonyms: 2,6,10-Trimethyl-5,9-undecadienal;Oncidal;2,6,10-Trimethyl-5,9-undecadien-1-al;Einecs 258-966-6
• CAS NO: 54082-68-7
• Molecular Formula: C14H24O
• Molecular Weight: 208.33976
• EINECS: 258-966-6
• Mol File: 54082-68-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 292.8°C at 760 mmHg
• Flash Point: 134.7°C
• Appearance: /
• Density: 0.853g/cm³
• Vapor Pressure: 0.00179mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: 2,6,10-trimethylundeca-5,9-dienal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,10-trimethylundeca-5,9-dienal(54082-68-7)
• EPA Substance Registry System: 2,6,10-trimethylundeca-5,9-dienal(54082-68-7)

Safety Data

• Hazardous Substances Data: 54082-68-7(Hazardous Substances Data)

Usage

Chemical Properties

Not found in nature, 2,6,10-Trimethyl-5,9-undecadienal is a clear, colorless to pale yellowish liquid. It has an aldehydic, floral odor reminiscent of nerolidol, with fruity nuances. It can be prepared fromgeranylacetone by Darzens reaction with ethyl chloroacetate through the corresponding glycidic ester, which is hydrolyzed and decarboxylated. 2,6,10-Trimethyl-5,9-undecadienal is used tomodify perfume compositions for soaps, detergents, and household products.

Trade name

Profarnesal (Symrise).

InChI:InChI=1/C14H24O/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15/h7,9,11,14H,5-6,8,10H2,1-4H3

Upstream product

• 905291-25-0 (E)-11,11-Dimethoxy-2,6,10-trimethyl-undeca-2,6-diene 
• 905291-16-9 (1E,5E)-1-Methoxy-2,6,10-trimethyl-undeca-1,5,9-triene 
• 3796-70-1 trans geranyl acetone 
• 105-39-5 chloroacetic acid ethyl ester 
• 75-09-2 dichloromethane 
• 1373874-66-8 (R,E)-2-(6,10-dimethylundeca-5,9-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 198268-26-7 (2R,5E,9E)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-2,6,10,N-tetramethylundeca-5,9-dienamide 
• 22339-13-5 (E)-9-iodo-2,6-dimethylnona-2,6-diene 
• 127516-27-2 (2R,5E,9E)-2,6,10-trimethylundeca-5,9-dien-1-ol 
• 1018781-53-7 C₁₅H₂₈O₂ 
• 198545-88-9 (2S,5E,9E)-2,6,10-trimethylundeca-5,9-dien-1-ol 

Relevant articles and documents

PROCESS FOR THE MANUFACTURE OF 2,6,10-TRIMETHYLUNDECA-5,9-DIENAL

The present invention relates to an improved process for the manufacture of 2,6,10-trimethylundeca-5,9-dienal (Darzens reaction, saponification, decarboxylation).

Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene

Enantioenriched secondary allylic carbamates have been deprotonated with sBuLi and reacted with boronic esters. In contrast to other electrophiles, high α-selectivity was observed and the boronate complexes were formed with almost complete retention of stereochemistry. The boronate complexes underwent a stereospecific 1,2-migration leading to tertiary allylic boronic esters with high er (>98:2). The scope of the reaction has been explored and found to embrace a broad range of both allylic carbamates and boronic esters. The methodology has been applied to an eight-step, stereoselective synthesis of each of the diastereoisomers of C30 botryococcene.

Liphagal, a selective inhibitor of PI3 kinase α isolated from the sponge Aka coralliphaga: Structure elucidation and biomimetic synthesis

Liphagal (1), a selective inhibitor of PI3K α, has been isolated from the marine sponge Aka coralliphaga collected in Dominica. The "liphagane" meroterpenoid carbon skeleton of liphagal (1) is new. A biomimetic total synthesis has been used to confirm the