19926-64-8

Usage

Uses

Used in Flavoring Industry:
(Z,E,E)-3,6,8-Dodecatrien-1-ol is used as a flavoring agent for its pleasant, fruity odor, adding a natural taste to various food products.
Used in Fragrance Industry:
(Z,E,E)-3,6,8-Dodecatrien-1-ol is used as a fragrance ingredient in the production of perfumes and colognes, contributing to their appealing scents.
Used in Cosmetics and Personal Care Industry:
(Z,E,E)-3,6,8-Dodecatrien-1-ol is used as a chemical intermediate in the synthesis of other compounds, which are then utilized in the manufacturing of various cosmetics and personal care products.
Used in Chemical Synthesis:
(Z,E,E)-3,6,8-Dodecatrien-1-ol is used as a chemical intermediate for the synthesis of other compounds, showcasing its versatility in different applications across various industries.

InChI:InChI=1/C12H20O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h4-7,9-10,13H,2-3,8,11-12H2,1H3/b5-4+,7-6-,10-9-

Upstream product

• 128120-09-2 3,6,8-dodecatrien-1-ol THP ether 
• 95331-75-2 2,4-dimethyl-3-pentyl (Z,Z,E)-3,6,8-decatrienoate 
• 128120-09-2 2-dodeca-3,6,8-trienyloxy-tetrahydro-pyran 
• 934236-99-4 (E)-oct-4-en-2-yn-1-ol toslyate 
• 807627-36-7 2-dodec-8-ene-3,6-diynyloxy-tetrahydro-pyran 
• 627-19-0 1-Pentyne 
• 66703-03-5 trans-1-iodo-1-pentene 
• 344397-46-2 (E)-oct-4-en-2-yn-1-ol 
• 88730-62-5 Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide 
• 16635-54-4 (Z)-2-hexenal 
• 130236-43-0 (E)-6-(2-tetrahydropyranyloxy)-hex-3-enyltriphenyl phosphonium iodide 
• 6728-26-3 (E)-2-Hexenal 
• 130236-41-8 (3E)-1-iodo-6-(2-tetrahydropyranyloxy)-hex-3-ene 
• 71655-17-9 (E)-3-hexen-1,6-diol 

Relevant academic research and scientific papers

Selective Proton Transfer of Unsaturated Esters. Syntheses of A Trail-Following Pheromone for Subterranean Termites and Megatomoic Acid

Deconjugative protonation of dienolates from (E)-2-alkenoate using potassium disilazide as the base gives (Z)-3-alkenoate predominantly.A trail-following pheromone for subterranean termites is synthesized stereoselectively with this method.Deconjugative protonation of trienolates from (E,E)-2,4-tetradecadienoates gives (E,Z)-3,5-tetradecanoates which is hydrolyzed to give Megatomoic acid, a sex pheromone for a black carpet beetle Attagenus megatoma.

Role of (3Z,6Z,8E)-dodecatrien-1-ol in trail following, feeding, and mating behavior of Reticulitermes hesperus

Trail pheromones mediate communication among western subterranean termites, Reticulitermes hesperus Banks. Repetitive passages of ≥28 termites were required to establish a pheromone trail and trails needed to be reinforced because they lasted 10 pg/cm were repellent to workers. Workers did not detect pheromone gradients, responding equally to increasing or decreasing gradients of dodecatrienol, and termite workers were not able to differentiate between different concentrations of dodecatrienol. Termites preferred dodecatrienol trails to 2-phenoxyethanol trails. Antennae played a key role in trail pheromone perception. Dodecatrienol acted as an arrestant for worker termites (10 fg/cm2) and male alates (5 ng/cm2), whereas sternal gland extracts from females attracted male alates. Workers and alates, upon contact with filter paper disks treated with higher doses (10 fg/cm2 and 5 ng/cm2, respectively) of dodecatrienol, were highly excited (increased antennation and palpation) and repeatedly returned to the treated disks. Dodecatrienol did not act as a phagostimulant when offered on a paper towel disk. Reticulitermes hesperus is highly responsive to dodecatrienol, and it may play an important role in orientation of workers and alates.

Syntheses and NMR analyses of the eight geometric isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trail pheromone

Eight geometric isomers of 3,6,8-dodecatrien-1-ol 1, the trail-following pheromone of subterranean termites (Reticulitermes sp. Banks), were synthesized via a Wittig olefination reaction. The convergent syntheses of 1 consisted of a combination of two fragments, each containing an olefin with a fixed configuration, by formation of a third double bond to give a mixture of two geometric isomers. The mixtures of 1 were resolved by recycle high-performance liquid chromatography methods. 1H and 13C NMR peak assignments of the individual isomers were accomplished by homonuclear COSY, and one-bond CH correlation spectroscopy.

FACILE R0UTES TO NATURAL ACYCLIC POLIENES. SYNTHESES OF SPILANTHOL AND TRAIL PHEROMONE FOR TERMITE

The synthetic procedures for spilanthol and trail-following pheromone for a southern subterranean termite were described.The syntheses heavily depend on the new diene synthesis using titanium reagent.