40642-38-4

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-Dodec-5-enol is used as a reactant in the stereoselective preparation of bacteriocin stereoisomers, which serve as antibacterial agents. These bacteriocins are essential in the development of new antibiotics to combat drug-resistant bacteria, as they can target specific bacterial strains with high precision and minimal side effects.
Used in Chemical Synthesis:
(Z)-Dodec-5-enol can also be utilized as a key intermediate in the synthesis of various organic compounds, such as fragrances, flavors, and other specialty chemicals. Its unique structure allows for selective reactions that can lead to the production of a diverse range of products with specific applications in different industries.

InChI:InChI=1/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h7-8,13H,2-6,9-12H2,1H3/b8-7-

Upstream product

• 694-54-2 tetrahydro-2H-2-pyranol 
• 13423-48-8 triphenylheptylphosphonium bromide 
• 111-71-7 heptanal 
• 34626-52-3 5-hydroxypentyltriphenylphosphonium bromide 
• 68820-33-7 (Z)-dodec-5-enal 
• 79837-88-0 cis-5-dodecenoic acid methyl ester 
• 1720-37-2 2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 
• 4221-03-8 5-hydroxypentanal 
• 2430-94-6 cis-dodec-5-enoic acid 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 1260379-16-5 (Z)-((dodec-5-enyloxy)methyl)benzene 
• 88109-70-0 n-5-dodecyn-1-ol 
• 17924-10-6 C₁₇H₃₂O₂ 
• 79837-79-9 (4-methoxy-4-oxobutyl)triphenylphosphonium brominde 

Downstream Products

• 16676-96-3 (Z)-5-dodecen-1-yl acetate 

Relevant academic research and scientific papers

Enantioselective synthesis of (2S,3′R,7′Z)-N -(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone

A concise enantioselective total synthesis of (2S,3′R,7′Z)-N- (3′-hydroxy-7′-tetradecenoyl)-homoserine lactone is described. Key feature of this protocol is a catalytic asymmetric hydrogenation and a prophenol-zinc-catalyzed diazo addition to imine reaction as genesis of chirality. Moreover, flexibility is built in the synthesis to generate enantioenriched analogs using catalytic amount of enantioenriched C 2-symmetric ligands.

Evaluation of aroma-active compounds in Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test

The aroma-active compounds of Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) were characterized by using gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA) techniques. Forty-one compounds were found to be aroma-active, which were mainly dominated by saturated and unsaturated aldehydes. The flavor dilution (FD) factor was within the range of 2-2048, and compounds having the highest FD factor were α-pinene, β-pinene, linalool, and 2-methoxy-3-(2- methylpropyl) pyrazine, including a few unknown compounds. On the basis of GC-O results, odor activity value (OAV) and relative flavor activity (RFA) were determined for aroma model reconstitution. These resembled the original aroma of the peel oil for the green, fatty, fresh, peely, floral, and tarry attributes, with the model solution derived from OAV being the closest to Pontianak oil. Omission tests were carried out to verify the significance of (Z)-5-dodecenal and 1-phenylethyl mercaptan as key compounds in the aroma of Pontianak orange peel oil.

Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium rhizobium Leguminosarum

The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3 -hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of ft leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

Improved synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major sex pheromone constituent of the potato pest Symmetrischema tangolias (Gyen)

An efficient six-step synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major component of the sex pheromone of the potato pest Symmetrischema tangolias (Gyen), is described, starting from the commercially available dihydropyran. The stereoselective formation of the 7Z double bond is accomplished by a Wittig reaction, while the 3E double bond is formed by a modified Knoevenagel condensation. The overall yield of the synthesis is 28%, giving the final product in high stereochemical purity (95%). The simplicity and the low cost of the herein reported synthesis suggest the potential practical use of the above pheromone in integrated management programs, for this serious insect pest.

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans

In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cychzation rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cychzed products can be easily converted into a hydroxy group with stereochemical retention.

SYNTHESIS OF A HIGHLY UNSATURATED FATTY ACID MOIETY OF LIPO OLIGOSACCHARIDES DETERMINING HOST-SPECIFICITY IN RHIZOBIUM

The phosphonate ethyl 6-(diethylphosphono)-2E,4E-hexadienoic acid is a suitable synthon for the highly stereoselective preparation of 2E,4E,6E,11Z-octadecatetraenoic acid and its 2E,4E,6E-analog.

Synthesis of (Z)-5-dodecenyl and (Z)-5-tetradecenyl acetates: Pheromone components of Lepidoptera noctuidae species

(Z)-5-Dodecenyl acetate (1) and (Z)-5-tetradecenyl acetate (2), the pheromone components of Lepidoptera noctuidae species have been synthesised by a new approach from the corresponding (Z)-4-undecenol (3) and (Z)-4-tridecenol (4), both of which have been obtained from a common intermediate, viz. the dianion of 4-pentyn-1-ol.

ω-HYDROXYALKYL-PHOSPHONIUM SALTS AS "INSTANT-YLID" COMPONENTS: EXTREMELY CONVENIENT AND HIGHLY CIS-SELECTIVE SYNTHESIS OF ALKENOL-TYPE PHEROMONES

In less than 2 hours, (Z)-alkenols of 97-98percent stereoisomeric purity may be prepared and isolated (!) if a new type of "instant-ylids" is used.