29837-19-2

Usage

Uses

Used in Pharmaceutical Industry:
(Z,E,Z)-undeca-1,3,5,8-tetraene is used as a precursor in the synthesis of various organic compounds for pharmaceutical applications. Its unique structure and reactivity allow for the creation of complex molecules that can be used in the development of new drugs and therapies.
Used in Food Industry:
In the food industry, (Z,E,Z)-undeca-1,3,5,8-tetraene is utilized as a component in the synthesis of additives and flavorings. Its presence in essential oils makes it a valuable contributor to the development of unique flavors and scents in the food products.
Used in Materials Science:
(Z,E,Z)-undeca-1,3,5,8-tetraene is used as a building block in materials science for the development of new materials with specific properties. Its structural characteristics and reactivity enable the creation of novel materials with potential applications in various fields.
Used in Organic Chemistry Research:
As a starting point for the synthesis of complex molecules, (Z,E,Z)-undeca-1,3,5,8-tetraene is used in organic chemistry research to explore new reaction pathways and develop innovative synthetic methods. This contributes to the advancement of the field and the discovery of new chemical compounds with diverse applications.

InChI:InChI=1/C11H16/c1-3-5-7-9-11-10-8-6-4-2/h3,5-9,11H,1,4,10H2,2H3

Upstream product

• 132565-82-3 Methanesulfonic acid (3Z,6Z)-1-vinyl-nona-3,6-dienyl ester 
• 35389-48-1 (5Z,8Z)-(+/-)-1,5,8-undecatrien-3-ol 
• 35389-48-1 (5Z,8Z)-Undeca-1,5,8-trien-3-ol 
• 50306-18-8 (Z)-(RS)-1,5-octadien-3-ol 
• 81717-80-8 5,8-undecadiyn-1-en-3-ol 
• 1573-66-6 hex-1-en-5-yn-3-ol 
• 67548-44-1 (2Z,5Z)-octa-2,5-dien-1-ol 
• 132565-81-2 Phosphoric acid diethyl ester (3Z,6Z)-1-vinyl-nona-3,6-dienyl ester 
• 15935-94-1 allylidenetriphenylphosphorane 
• 79728-53-3 (2Z,5Z)-2,5-octadienal 

Relevant academic research and scientific papers

Pericyclic Reactions in Nature: Evidence for a Spontaneous -Hydrogen Shift and an 8?e Electrocyclic Ring Closure in the Biosynthesis of Olefinic Hydrocarbons from Marine Brown Algae (Phaeophyceae).

The stereochemistry of the algal C11H16 hydrocarbon giffordene 3 results from a spontaneous -sigmatropic hydrogen shift of the thermolabile (1,3Z,5Z,8Z)-undecatetraene 8.An 8?e electrocyclisation of (1,3Z,5Z,7E)-nonatetraene 9 is substantiated for the synthesis of 7-methylcyclooctatriene 5, a product of the Mediterranean brown alga Cutleria multifida.Low temperature syntheses (-30 deg C) of the thermolabile precursors 8 and 9 are described.The activation energies of the -sigmatropic hydrogen shift 8 -> 3 (Ea = 67.4 kJ mol-1) and of the 8?e electrocyclisation 9 -> 5 (Ea = 59.4 kJ mol-1) are the lowest values currently known for natural pericyclic reactions.

Mint composition

The present invention relates to a mint composition, which comprises a mint substance and a 1,3,5,8-undecatetraene; and a fragrance-added or flavored product containing the mint composition. The mint composition has enhanced diffusing property and intensity of fragrance or flavor showing a high impact, shows excellent natural feeling and taste and also has excellent durability in fragrance or flavor.

Stereospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae

Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five stereoisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae.Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs.The uniform enynes (>98percent purity) are then stereospecifically reduced to (Z)-alkenes with Zn(Cu/Ag) in aq.MeOH at r.t. 13C- and 1H-NMR data of the new tetraenes are presented.Biosynthetically, giffordene (9f) originates from dodeca-3,6,9-trienoic acid via an unstable (3Z,5Z,8Z)-1,3,5,8-undecatetraene followed by a thermally allowed antarafacial 1,7-sigmatropic hydrogen shift to the (2Z,4Z,6E,8Z)-isomer 9f.

Synthesis of Isomeric 1,3,5,8-Undecatetraenes

(3E,5Z,8Z)-1,3,5,8-Undecatetraene (1a) is the smelling principle of the gametes of the brown alga Spermatochnus paradoxus.The synthesis of the isomeric 1,3,5,8-undecatetraenes 1a - c and their spectral properties are described.