16356-11-9

Basic information

• Product Name: 1,3,5-UNDECATRIENE
• Synonyms: 1,3,5-UNDECATRIENE;FEMA 3795;UNDECATRIENE;Undeca-1,3,5-triene (Isomer 1);1,3,5-Undecatriene (mixture of isomers);undeca-1,3,5-triene;1 3 5-UNDECATRIENE 70+% MIXTURE OF &;CHEMICAL NAME: 1,3,5-UNDECATRIENE
• CAS NO: 16356-11-9
• Molecular Formula: C₁₁H₁₈
• Molecular Weight: 150.26
• EINECS: 240-416-1
• Product Categories: Alphabetical Listings;Flavors and Fragrances;Q-Z
• Mol File: 16356-11-9.mol

Chemical Properties

• Boiling Point: 280-285 °C(lit.)
• Flash Point: 172 °F
• Appearance: COLORLESS LIQUID
• Density: 0.79 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.336mmHg at 25°C
• Refractive Index: n20/D 1.513(lit.)
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 1,3,5-UNDECATRIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-UNDECATRIENE(16356-11-9)
• EPA Substance Registry System: 1,3,5-UNDECATRIENE(16356-11-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 2
• RTECS: YQ2833000
• Hazardous Substances Data: 16356-11-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
1,3,5-Undecatriene is used as a flavor compound for its green, vegetative, waxy, cucumber, and chicken fatty notes, as well as its fruitiness. It is particularly suitable for enhancing the taste and aroma of various food products, such as fruits, vegetables, and beverages.
Used in Fragrance Industry:
1,3,5-Undecatriene is used as a fragrance ingredient for its green, melon, pineapple, and fruity odor. It is widely utilized in the creation of perfumes, colognes, and other scented products to provide a fresh, natural, and appealing scent.
Used in Natural Products:
1,3,5-Undecatriene is found in various natural sources, such as apple, celery, kiwi, mandarin, parsley, passion fruit, pear, peach, pineapple, peppermint, and galbanum oil. It is used as a natural additive in the production of these products to enhance their taste and aroma, contributing to their overall sensory appeal.

Preparation

By dehydration of undeca-1,5-dien-3-ol.

InChI:InChI=1/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

• 25152-84-5 trans,trans-2,4-decadienal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1457-42-7 pyridazinyl-N-oxide 
• 61307-38-8 1-heptynylmagnesium bromide 
• 109921-65-5 (Z)-hept-1-enylmagnesium bromide 
• 593-60-2 Vinyl bromide 
• 19493-09-5 Methylenetriphenylphosphorane 
• 109921-65-5 C₇H₁₃BrMg 
• 3001-72-7 DBN 
• 107172-51-0 (E)-undeca-1,5-dien-3-ol 
• 56722-26-0 1-bromo-(2E,5Z)-2,5-undecadiene 
• 20432-40-0 (E)-penta-2,4-dienal 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 2363-88-4 deca-2,4-dienal 

Downstream Products

• 56318-85-5 3-n-Hepten-1-yl-4-n-nonadien-1,3-yl-cyclohexen 
• 56318-85-5 3-((E)-Hept-1-enyl)-4-((1E,3E)-nona-1,3-dienyl)-cyclohexene 
• 1379606-27-5 N,N'-((2E,4E)-undeca-2,4-diene-1,6-diyl)bis(4-methyl-N-tosylbenzenesulfonamide) 
• 20285-14-7 1-n-Heptyl-2-n-nonyl-benzol 

Relevant articles and documents

A NOVEL SYNTHESIS OF LINEAR POLYENES VIA CONJUGATE ADDITION OF CUPRATES TO α,β-γ,δ-DIUNSATURATED SULFONES FOLLOWED BY SO2 EXTRUSION

The two 1,3-butadienyl 2-propenyl sulfones 5 and 6, 1,3,5-heptatriene synthons, have been transformed into the tri- and tetraenes 1 - 4 by alkylcuprate addition and Ramberg-Baecklund SO2 extrusion.The reaction stereochemistry is discussed.

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond

A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.

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.

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.