20085-73-8

Basic information

• Product Name: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester
• Synonyms: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester
• CAS NO: 20085-73-8
• Molecular Formula: C₁₇H₂₈O₂
• Molecular Weight: 264.4
• Mol File: 20085-73-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester(20085-73-8)
• EPA Substance Registry System: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester(20085-73-8)

Safety Data

• Hazardous Substances Data: 20085-73-8(Hazardous Substances Data)

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 3879-26-3 (Z)-nerylacetone 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 63284-81-1 1,1-dimethoxy-4-methyl-8-oxonon-4Z-ene 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 25996-10-5 (Z)-neryl bromide 
• 72444-96-3 (Z)-2-acetyl-5,9-dimethyldeca-4,8-dienoic acid ethyl ester 
• 927-80-0 1-ethoxyacetylene 
• 13950-57-7 ethyl α-(diphenylmethylsilyl)acetate 
• 594-27-4 tetramethylstannane 
• 247113-11-7 ethyl 3-(((trifluoromethyl)sulfonyl)oxy)-7,11-dimethyldodeca-2(E),6(Z),10-trienoate 
• 676-58-4 methylmagnesium chloride 
• 477960-40-0 ethyl (2E,6Z)-3-[(diethoxyphosphoryl)oxy]-7,11-dimethyl-2,6,10-dodecatrienoate 
• 20536-36-1 neryl chloride 

Downstream Products

• 16106-95-9 (2Z,6Z)-farnesol 
• 3879-60-5 2E,6Z-farnesol 
• 6895-56-3 β-cis-bergamotene 

Relevant articles and documents

UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY

This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is: Formula (I).

Synthesis of farnesol isomers via a modified wittig procedure

(Chemical Equation Presented) The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of β-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons condensation with triethyl phosphonoacetate and reduction of the resulting ester.

Synthesis and biological evaluation of the geometric farnesylated analogues of the a-factor mating peptide of Saccharomyces cerevisiae

The a-factor of Saccharomyces cerevisiae is a dodecapeptide pheromone (YIIKGVFWDPAC-(Farnesyl)-OCH3, 1), in which post-translational modification with a farnesyl isoprenoid and carboxymethyl group is required for full biological activity. This peptide has been used as a model system to explore the biological function of the farnesylcysteine moiety, which is found on and required for the biological activity of many key mammalian proteins. The objective of this particular study was the determination of the biological effect of double bond isomerization of the natural E,E-farnesyl moiety on the biological activity of the a-factor. A unified, stereoselective synthetic route to the three geometric isomers of E,E-farnesol (12, 13, and 14) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the β-ketoester 22 to give either 23 or 25. The three farnesol isomers were converted to the corresponding isomeric a-factors (9, 10 and 11) via a modified version of a previously utilized synthetic route. Biological evaluation of these peptides indicates that, surprisingly, all three possess nearly equivalent activity to the natural a-factor bearing the E,E-farnesyl moiety.