2774-84-7

Usage

Uses

Used in Pharmaceutical Industry:
10-Undecyn-1-ol is used as an antifungal agent for its ability to combat fungal infections. Its antifungal activity makes it a valuable component in the development of medications and treatments targeting various fungal pathogens.
Used in Synthetic Chemistry:
10-Undecyn-1-ol is used as a reagent in the preparation of 11-bromo-undec-1-yne by reacting with carbon tetrabromide and triphenylphosphine. This reaction showcases its utility in creating complex organic compounds for further research and development.
Used in Esterification Processes:
10-Undecyn-1-ol is used as a reactant in the esterification of pentanoic and stearic acids in the presence of various lipases. This application highlights its role in the production of esters, which have a wide range of uses in the chemical and pharmaceutical industries.
Used as an Intermediate in Organic Synthesis:
10-Undecyn-1-ol serves as an intermediate in synthetic chemistry, contributing to the synthesis of more complex molecules and compounds. Its versatility in participating in various chemical reactions makes it a valuable component in the development of new materials and products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7884, 1995 DOI: 10.1021/jo00129a031

InChI:InChI=1/C11H20O/c1-2-3-4-5-6-7-8-9-10-11-12/h1,12H,3-11H2

Upstream product

• 94030-75-8 ethyl ester of dodec-11-ynoic acid 
• 2777-65-3 undec-10-ynoic acid 
• 24724-18-3 10,11-Dibromo-1-undecanol 
• 2777-66-4 methyl 10-undecynoate 
• 34683-71-1 undec-2-yn-1-ol 
• 54299-09-1 3-n-undecyn-1-ol 
• 51887-25-3 tridec-2-yn-1-ol 
• 88517-99-1 2-undecynyltetrahydro-2H-pyran-2-yl ether 
• 103680-94-0 undec-10-ynal 
• 5390-04-5 pent-1-yn-5-ol 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 111-81-9 Methyl 10-undecenoate 
• 3452-09-3 1-nonyne 
• 112-38-9 10-undecenoic acid 

Downstream Products

• 71317-72-1 undec-10-yn-1-yl bromide 
• 478404-25-0 10-undecyn-1-yl N-phenylcarbamate 
• 51953-88-9 1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 126542-66-3 3,6-Diphenyl-5-undec-10-ynyloxy-[1,2,4]triazine 
• 132260-32-3 tert-butyldimethyl(undec-10-yn-1-yloxy)silane 
• 89329-65-7 11-(4-methylbenzenesulfonyloxy)-1-undecyne 
• 92266-90-5 10,12-pentacosadiyne-1-ol 
• 506-45-6 22-hydroxydocosanoic acid 
• 112-43-6 10-Undecen-1-ol 
• 113308-95-5 11-(trimethylsilyl)undec-10-yn-1-ol 
• 415680-04-5 o-(9-hydroxy-1-undecynyl)thioanosole 
• 473932-32-0 11-[(1,2,3,4,5-pentaphenylsilolyl)oxy]-1-undecyne 
• 473932-31-9 11-phenyl-undec-10-yn-1-ol 
• 868132-34-7 10-(tert-butyldiphenylsilanyloxy)decanoic acid undec-10-ynyl ester 

Relevant academic research and scientific papers

A new stereocontrolled, pyrylium-based route to conjugated dienynes: The first synthesis of Carduusyne A

A new stereocontrolled route to conjugated dienynes is described, utilising organometallic addition to pyrylium salts followed by Wittig homologation and dehydrohalogenation. The utility of this methodology is illustrated in the first total synthesis of the marine metabolite Carduusyne A.

Stereoselective synthesis of C3–C17 and C18–C34 subunits of bullatanocin utilizing α-chloro sulfide intermediates

A convergent synthesis of bullatanocin is envisaged by the union of C18–C34, C3–C17 and the butenolide subunits. The synthesis of the C3–C17 and C18–C34 subunits is disclosed that takes advantage of the chirality of tartaric acid for 1,2-asymmetric induct

Enzyme kinetics and inhibition of histone acetyltransferase KAT8

Lysine acetyltransferase 8 (KAT8) is a histone acetyltransferase (HAT) responsible for acetylating lysine 16 on histone H4 (H4K16) and plays a role in cell cycle progression as well as acetylation of the tumor suppressor protein p53. Further studies on its biological function and drug discovery initiatives will benefit from the development of small molecule inhibitors for this enzyme. As a first step towards this aim we investigated the enzyme kinetics of this bi-substrate enzyme. The kinetic experiments indicate a ping-pong mechanism in which the enzyme binds Ac-CoA first, followed by binding of the histone substrate. This mechanism is supported by affinity measurements of both substrates using isothermal titration calorimetry (ITC). Using this information, the KAT8 inhibition of a focused compound collection around the non-selective HAT inhibitor anacardic acid has been investigated. Kinetic studies with anacardic acid were performed, based on which a model for the catalytic activity of KAT8 and the inhibitory action of anacardic acid (AA) was proposed. This enabled the calculation of the inhibition constant Ki of anacardic acid derivatives using an adaptation of the Cheng-Prusoff equation. The results described in this study give insight into the catalytic mechanism of KAT8 and present the first well-characterized small-molecule inhibitors for this HAT.

Stereoselective Synthesis of Perfluoroalkylated (E,E)-Dienes from Perfluoroalkylated Alkynes. The Synthesis of Fluorinated Analogs of Lepidoptera Pheromones

Pd(dba)2 -HOAc catalyzed the isomerization of 1-perfluoroalkyl-1-alkynes to give 1-perfluoroalkyl-(1E,3E)-dienes in good yield and stereoselectivity; the fluorinated analogs of Lepidoptera species sex pheromone attractants were synthesized applying this method.

Chemoproteomic profiling reveals cellular targets of nitro-fatty acids

Nitro-fatty acids are a class of endogenous electrophilic lipid mediators with anti-inflammatory and cytoprotective effects in a wide range of inflammatory and fibrotic disease models. While these beneficial biological effects of nitro-fatty acids are mainly attributed to their ability to form covalent adducts with proteins, only a small number of proteins are known to be nitro-alkylated and the scope of protein nitro-alkylation remains undetermined. Here we describe the synthesis and application of a clickable nitro-fatty acid probe for the detection and first global identification of mammalian proteins that are susceptible to nitro-alkylation. 184 high confidence nitro-alkylated proteins were identified in THP1 macrophages, majority of which are novel targets of nitro-fatty acids, including extended synaptotagmin 2 (ESYT2), signal transducer and activator of transcription 3 (STAT3), toll-like receptor 2 (TLR2), retinoid X receptor alpha (RXRα) and glucocorticoid receptor (NR3C1). In particular, we showed that 9-nitro-oleate covalently modified and inhibited dexamethasone binding to NR3C1. Bioinformatic analyses revealed that nitro-alkylated proteins are highly enriched in endoplasmic reticulum and transmembrane proteins, and are overrepresented in lipid metabolism and transport pathways. This study significantly expands the scope of protein substrates targeted by nitro-fatty acids in living cells and provides a useful resource towards understanding the pleiotropic biological roles of nitro-fatty acids as signaling molecules or as multi-target therapeutic agents.

IMMUNOTHERAPEUTIC AGENT

Compounds for use in the treatment of sepsis and/or the prevention or treatment of post-sepsis syndrome.

Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration

The first total synthesis of a marine derived polyacetylene, distaminolyne A, and its enantiomer were achieved from the commercially available undec-10-en-1-ol. A key proline-catalyzed asymmetric α-aminooxylation of an aldehyde intermediate was used to in

Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization

A highly attractive route toward macrolactones, which form the cyclic scaffold of a multitude of diverse natural compounds, is described. Although many chemical approaches to this structural motif have been explored, an asymmetric variant of the cyclization is unprecedented. Herein we present an enantioselective macrolactonization through an intramolecular atom-economical rhodium-catalyzed coupling of ω-allenyl-substituted carboxylic acids. The use of a modified diop ligand, chiral DTBM-diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β-unsaturated carboxylic acids and depsipeptides, and provided the desired macrocycles with very high enantio- and diastereoselectivity.

In situ proteome profiling of C75, a covalent bioactive compound with potential anticancer activities

A library of cell-permeable, minimally tagged C75 analogues was synthesized and used to uncover biological targets in human liver cancer cells. Known targets of C75, namely FASN and CPT1A, together with other unknown targets, including PDIA3, TFRC, and GAPDH, were thus identified.

Triphenylene discotic liquid crystal trimers synthesized by Co 2(CO)8-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

The synthesis of star-shaped discotic liquid crystal trimers using Co 2(CO)8-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition reaction is reported. The trimers consist of three triphenylene discotic units linked to a central 1,2,4-trisubstituted benzene ring via flexible spacers. The trimers were synthesized in the yields up to 70% by mixing the monomers with 10 mol % of Co2(CO)8 as the catalyst in refluxing 1,4-dioxane. The liquid crystalline properties were investigated by using polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Trimer 4 with an ester connecting group and a longer spacer exhibited a rectangular columnar mesophase, while 5b and 5c possessing an ether linkage and a shorter spacer display a hexagonal columnar mesophase. The connecting functional group and the length of the flexible spacer between the central benzene ring and the triphenylene units have pivotal influence on the mesomorphism.