51447-08-6

Usage

Uses

Used in Fragrance Industry:
(E,Z)-Undeca-1,3,5-triene is used as a fragrance ingredient for its strong green, galbanum-like odor. It is an important component in the formulation of perfumes and other scented products due to its distinctive and appealing scent.
Used in Flavor Industry:
(E,Z)-Undeca-1,3,5-triene is used as a flavoring agent for its unique odor, which can enhance the taste and aroma of various food and beverage products.
Used in Essential Oils:
(E,Z)-Undeca-1,3,5-triene is used in the production of essential oils, particularly galbanum oil, where it is the primary odor-determining constituent. This oil is widely used in aromatherapy and other therapeutic applications.
Used in Chemical Synthesis:
(E,Z)-Undeca-1,3,5-triene is used as a starting material or intermediate in the synthesis of various chemicals and compounds, taking advantage of its unique chemical properties and reactivity.
Used in Research and Development:
(E,Z)-Undeca-1,3,5-triene is utilized in research and development for studying its chemical properties, potential applications, and the development of new synthetic routes for its production.

Trade name

Galbanolene Super (Firmenich), Undecatriene 10% (Givaudan).

InChI:InChI=1S/C11H18/c1-3-5-7-9-11-10-8-6-4-2/h3,5,7,9,11H,1,4,6,8,10H2,2H3/b7-5+,11-9-

Upstream product

• 56318-72-0 undeca-1,2,4c-triene 
• 1457-42-7 pyridazinyl-N-oxide 
• 109921-65-5 (Z)-hept-1-enylmagnesium bromide 
• 3525-31-3 n-pentyl lithium 
• 2567-32-0 Pyrylium perchlorate 
• 19493-09-5 Methylenetriphenylphosphorane 
• 2548-87-0 (E)-2-Octenal 
• 89942-12-1 (E)/(Z)-1-bromo-1-heptene 
• 70600-64-5 trimethyl[(E)-non-3-en-1-ynyl]silane 
• 115084-75-8 (1Z,3E)-1-trimethylsilyl-1,3-nonadiene 
• 61307-38-8 1-heptynylmagnesium bromide 
• 593-60-2 Vinyl bromide 
• 86826-43-9 Pyrrolidine-1-carbodithioic acid (2E,4E)-1-trimethylsilanylmethyl-deca-2,4-dienyl ester 
• 25152-84-5 trans,trans-2,4-decadienal 

Downstream Products

• 1379606-27-5 N,N'-((2E,4E)-undeca-2,4-diene-1,6-diyl)bis(4-methyl-N-tosylbenzenesulfonamide) 
• 56318-85-5 3-((E)-Hept-1-enyl)-4-((1E,3E)-nona-1,3-dienyl)-cyclohexene 
• 56318-84-4 5-pentyl-cyclohexa-1,3-diene 

Relevant academic research and scientific papers

METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE

PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

An approach to the regioselective diamination of conjugated di- and trienes

It's do or diaminate: The selective diamination of 1,3-butadienes in the presence of hypervalent iodine reagents has been developed. This oxidation process proceeds with complete selectivity in favor of diamination. Depending on the substrate, it proceeds either with 1,2- or 1,4-regioselectivity (see scheme). Copyright

Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene

(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.

A new synthetic route to 1,3,5-undecatrienes and fucoserratene

A new procedure for preparing natural alkatrienes, fucoserratene and 1,3,5-undecatrienes, was developed. The key step of both syntheses is stereoselective formation of double bonds by the Wittig reaction starting from (E)-4,4-dimethoxy-2-butenal.

Bridging the final gap in stereocontrolled Wittig reactions: Methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity

After treatment with an appropriate base (butyllithium or sodium amide), 2-alkenyltris(2-methoxymethoxyphenyl)phosphonium salts carrying an allyl, crotyl, or prenyl (3-methyl-2-butenyl) side chain condense with saturated or unsaturated aldehydes to give conjugated dienes with Z/E ratios ranging from 90:10 to >99:1 and averaging 96:4. Owing to steric congestion, yields are only moderate (on average 41%; extremes 10-79%). The nonvolatile tris(2- methoxymethoxyphenyl)phosphine oxide by-product can be readily isolated and reduced to recover the phosphane starting material, or it may be hydrolyzed to the water-soluble tris(2-hydroxyphenyl)phosphine oxide.

The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes

Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.

An efficient synthesis of 1,3(E),5(Z), 1,3(E),5(E)and 1,3(Z),5(Z)-trienes: Application to the synthesis of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate

The (Pd-Cu)-catalyzed reactions of trimethylsilyl acetylene with (E) or (Z)-chloroenynes, or 1-chloro-(1E,3E)-dienes, followed by desilylation and zinc-reduction of the triple bonds led respectively to (3E,5Z), (3Z,5Z) and (3E,5E)-trienes. Application to the syntheses of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate has been realized.

Stereoselective synthesis of polyenes via Heck coupling of vinylboronate esters

E- and Z-1-alkenyl iodides react with vinylboronate pinacol ester 1 under palladium(0) catalysed, Heck conditions to provide polyenylboronates in moderate yields after purification. The addition of either silver(I) or thallium(I) salts to the reaction mixture is essential. Alkenyl bromides are unreactive under identical reaction conditions.

Process for the preparation of polyunsaturated olefins

A process for the preparation of a polyunsaturated olefinic compound, i.e. undeca-1,3,5-triene, in its (3E,5Z) isomeric form, consisting of four consecutive steps starting from deca-1,4-diyne, is disclosed. Said process has the advantage of making it possible to obtain the desired isomer in its essentially pure form.

Use of cis-3-cyclobutene-1,2-dimethanol in stereoselective routes to some naturally occurring conjugated dienes and trienes

Thermal electronic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alka-2,4-dienals exclusively, and this process is exploited en route to various isomeric naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates from a single precursor, cis-3-cyclobutene-1,2-dimethanol 4.