2777-65-3

Basic information

• Product Name: 10-UNDECYNOIC ACID
• Synonyms: 10-UNDECYNOIC ACID;LABOTEST-BB LT00233091;TIMTEC-BB SBB008483;undec-10-ynoic acid;10-Undecynoic acid 95%;Hendecynoic acid;Undec-1-yn-11-oic acid
• CAS NO: 2777-65-3
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.26
• EINECS: 220-471-8
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;Diyne Compounds (LB Films);Functional Materials;LB Films;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 2777-65-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 40-42 °C(lit.)
• Boiling Point: 180 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.9898 (rough estimate)
• Vapor Pressure: 0.000317mmHg at 25°C
• Refractive Index: 1.4066 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 4.78±0.10(Predicted)
• Water Solubility: Sparingly Soluble in water.
• BRN: 1704918
• CAS DataBase Reference: 10-UNDECYNOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 10-UNDECYNOIC ACID(2777-65-3)
• EPA Substance Registry System: 10-UNDECYNOIC ACID(2777-65-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: YQ3683000
• F: 10-23
• Hazardous Substances Data: 2777-65-3(Hazardous Substances Data)

Usage

Description

10-Undecynoic acid (10-UDYA, UDY) is an acetylenic fatty acid known for its highly selective irreversible inhibition of hepatic ωand ω-1-lauric acid hydroxylases. It has been synthesized through the dehydrobromination of 10-undecenoic acid and is involved in various applications across different industries.

Uses

Used in Chemical Synthesis:
10-Undecynoic acid is used as a key component in the synthesis of copolyesters, contributing to the development of new materials with specific properties.
Used in Surface Chemistry:
10-Undecynoic acid serves as a model compound for investigating microwave-assisted surface click reactions, which are catalyzed with Cu(II)/sodium L-ascorbate. This application aids in understanding and optimizing surface reaction processes.
Used in Biochemical Assays:
In the field of biochemistry, 10-Undecynoic acid is employed as a biochemical probe in assays for the microsomal hydroxylation of lauric acid (LA). It is utilized in conjunction with high-performance liquid chromatography (HPLC) and flow-through radiochemical detection to study enzyme activity.
Used in Material Science:
10-Undecynoic acid is involved in the formation of molecular layers by adsorbing on fluorite surfaces, which can be crucial for various material applications and properties.
Used in Nanotechnology:
In the supercritical hydrothermal synthesis of iron oxide nanoparticles, 10-Undecynoic acid plays a role in the process, potentially influencing the size, shape, and properties of the nanoparticles produced.
Overall, 10-Undecynoic acid is a versatile compound with applications in chemical synthesis, surface chemistry, biochemistry, material science, and nanotechnology, showcasing its importance in various scientific and industrial fields.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 969, 1963Synthetic Communications, 21, p. 1941, 1991 DOI: 10.1080/00397919108021786

InChI:InChI=1/C11H18O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h1H,3-10H2,(H,12,13)

Upstream product

• 112-38-9 10-undecenoic acid 
• 6308-96-9 10,11-dibromo-undecanoic acid 
• 2774-84-7 undec-10-yn-1-ol 
• 103680-94-0 undec-10-ynal 
• 111-81-9 Methyl 10-undecenoate 
• 2777-66-4 methyl 10-undecynoate 

Downstream Products

• 2777-66-4 methyl 10-undecynoate 
• 26509-60-4 undec-10-ynoic acid propyl ester 
• 94030-75-8 ethyl ester of dodec-11-ynoic acid 
• 7333-25-7 10,12-octadecadiynoic acid 
• 112-38-9 10-undecenoic acid 
• 28393-02-4 10,12-docosadiynedioic acid 
• 506-45-6 22-hydroxydocosanoic acid 
• 78774-39-7 22-Brom-docosansaeure 
• 111-20-6 1,10-decanedioic acid 
• 478404-25-0 10-undecyn-1-yl N-phenylcarbamate 
• 109568-09-4 N-methyl-undec-10-ynanilide 
• 627-90-7 ethyl undecanoate 

Relevant articles and documents

An improved procedure for the synthesis of terminal and internal alkynes from 10-undecenoic acid

A remarkable solvent preference for dehydrobromination to yield 10-Undecynoic acid (5) and 9-Undecynoic acid (6) is observed in the case of 10,11-dibromoundecanoic acid (1). Thus, 10-Undecenoic acid can be easily and quantitatively converted to 6 in PEG-400, while 5 is produced in PEG-200. 5 can also be obtained in non-polar solvents with PEG-200/400 as a phase transfer catalyst.

Synthesis and functionalization of vinylsulfide and ketone-containing aliphatic copolyesters from fatty acids

A series of novel aliphatic copolyesters bearing vinylsulfide and ketone functional groups were synthesized via lipase catalyzed polycondensation of vegetable oil derivatives. The vinylsulfide-containing hydroxyacid (VSHA) from 10-undecenoic fatty acid and the ketone-containing hydroxyester (KHE) from methyl oleate were used to obtain random copolymers and further sequential and single-step strategies involving the reactions with thiol and oxyamine were investigated. Good agreement between product and feed stoichiometries was achieved in both reactions for sequential modification, and the order of addition seems not to be a significant parameter. One pot functionalization allows for the single step modification, but not quantitative reactions were achieved.

Iron-Catalyzed Aerobic Oxidation of Aldehydes: Single Component Catalyst and Mechanistic Studies

An aerobic oxidation of aldehydes towards carboxylic acids in MeCN using 1 atm of pure oxygen or oxygen in air as the oxidant and a catalytic amount of single component catalyst, Fe(NO3)3·9H2O, has been developed. Carboxylic acids with different synthetically useful functional groups were obtained at room temperature. Two mechanistic pathways have been proposed based on isotopic labeling, NMR monitoring, and control experiments. The practicality of this reaction has been demonstrated by conducting several 50 mmol-scale reactions using pure oxygen or an air-flow of ~30 mL/min.

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.