19754-57-5

Usage

Physical state

Clear, colorless liquid

Solubility

Insoluble in water, soluble in organic solvents

Uses

Reagent in organic synthesis, building block in pharmaceutical production, solvent, and in the manufacture of flavor and fragrance compounds

Toxicity

Low toxicity, considered relatively safe for use in controlled laboratory settings with proper handling and disposal according to safety guidelines.

InChI:InChI=1/C13H25ClO2/c14-10-6-3-1-2-4-7-11-15-13-9-5-8-12-16-13/h13H,1-12H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 23144-52-7 8-chlorooctan-1-ol 
• 629-41-4 1,8-Octanediol 
• 2050-23-9 diethyl suberate 

Downstream Products

• 71394-01-9 (E)-12-tetradec-9-yn-12-en-1-yl acetate 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 68516-29-0 1-(Tetrahydropyran-2-yloxy)tetradec-12E-en-9-yne 
• 42521-46-0 Tetradeca-cis-9,trans-12-dien-1-ol 
• 19754-59-7 tetrahydro-2-(9-tetradecynyloxy)pyran 

Relevant academic research and scientific papers

Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta

We have recently reported the synthesis of a platinum(II) complex, made of estradiol, the female sex hormone, and a cisplatin analog, an anticancer drug, linked together by an eleven carbon atoms chain. The novel estradiol-Pt(II) hybrid molecule was synthesized in nine chemical steps with 10% overall yield. This new compound has been tested in vitro on estrogen-dependent (MCF-7) and -independent (MDA-MD-231) (ER+ and ER-) cell lines. Interestingly, the biological activity was quite significant, more potent than that of cisplatin, the compound currently used in chemotherapy. The estrogen receptor binding affinity (ERBA) of this compound was very similar to that of 17β-estradiol (E2) on both estrogen receptors (ERs), α and β. In order to further study this type of molecule, we have decided to synthesize several analogs with the same estrogenic scaffold but with various chain lengths separating the estradiol from the toxic part of the molecule. This was planned in order to study the effect of the length of the linking chain on the biological activity of the hybrids. Four E2-Pt(II) hybrid molecules having 6-14 carbon atoms linking chain have been synthesized using a new synthetic methodology. They are synthesized in only eight chemical steps with 21% overall yield. The 17β-estradiol-linked platinum(II) complexes have been tested for their receptor binding affinity as well as for their cytocidal activity on several breast cancer cell lines. The synthesis and biological results are reported herein.

SYNTHESIS OF THE SEX PHEROMONE OF THE GRAIN MOTH Ephestia Elutella

A most convenient synthesis of tetradeca-9Z,12E-dien-1-ol and its acetate - components of the sex pheromone of the grain moth - has been carried out on the basis of a scheme for obtaining a cis-1,trans-4-dienic system.

Improved synthesis of (9Z)-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer

The terminal dienyne of (9Z)-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer, was constructed by coupling a vinyl iodide precursor with commercially available 1-buten-3-yne with Pd catalysis, resulting in a short and efficient synthesis of the pheromone.

SYNTHESIS AND USE OF OMEGA-3 AND OMEGA-6 VERY LONG CHAIN POLYUNSATURATED FATTY ACIDS (VLC-PUFA)

The invention provides methods of synthesizing omega-3 and omega-6 very long chain polyunsaturated fatty acids (VLC- PUFAs, C28-C42:4,5 and 6), analogs and derivatives thereof, pharmaceutical compositions containing these isolated VLC-PUFA compounds and therapeutic uses therefor.

Ethynylation of the ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamide complex

A new operationally simple and highly efficient procedure for the ethynylation of ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamine complex in N,N-dimethylacetamide is described.

SYNTHESIS OF HIGHER ACETYLENIC ALCOHOLS

The alkylation of 1-alkynes in various solvents was investigated, and the optimum conditions for the production of acetylenic alcohols were obtained.

Macrocyclic Lactone Formation through Sulfide Contraction. Synthesis of (+/-)-Diplodialide A

A methodology for the synthesis of macrocyclic β-keto-lactones from ω-hydroxy thioamides is described.The hydroxy thioamides were esterified with chloroacetyl chloride, and the resulting chloro esters underwent Eschenmoser sulfide contraction when treated with sodium iodide, diisopropylethylamine, and triethyl phosphite in acetonitrile.The β-keto lactones were obtained in 25-58 percent yield.The utility of the method was demonstrated by synthesis of diplodialide A.

(Z)-9-Tetradecen-1-ol formate and its use as a communication disruptant for Heliothis

(Z)-9-Tetradecen-1-ol formate [(Z)-9-TDF], a chemical of nonbiological origin, was prepared and found to have excellent potential as an insect control agent for the corn earworm, Heliothis zea (Boddie) and tobacco budworm, H. virescens (F.). Mating of H. zea and H. Virescens moths exposed in the field to an atmosphere permeated with (Z)-9-TDF was greatly reduced. The chemical can be used alone to inhibit mating of H. zea or H. virescens or it can be dispensed together with other mating inhibitors to suppress mating in several pest species simultaneously.