40165-88-6

Usage

Uses

Used in Antimicrobial Applications:
3-Hydroxyundecanoic acid is used as an antimicrobial agent for its ability to inhibit the growth of harmful microorganisms. This property makes it a valuable component in various applications, including:
Used in Healthcare Industry:
3-Hydroxyundecanoic acid is used as a sanitizing agent in hospitals and other medical facilities to maintain a hygienic environment and reduce the risk of infections. Its effectiveness against a wide range of pathogens makes it a promising candidate for improving patient safety and overall healthcare quality.
Used in Cosmetic Industry:
3-Hydroxyundecanoic acid is used as a preservative and antimicrobial agent in cosmetic formulations. Its ability to inhibit microbial growth helps to extend the shelf life of products and ensure their safety for consumers. Additionally, it may contribute to the development of cosmetics with enhanced skin health benefits due to its antimicrobial properties.

Upstream product

• 124-19-6 nonan-1-al 
• 105-36-2 ethyl bromoacetate 
• 111-66-0 oct-1-ene 
• 124-38-9 carbon dioxide 
• 3536-96-7 vinylmagnesium chloride 
• 112-37-8 undecylenic acid 
• 85028-98-4 (4R,6R)-4,6-dimethyl-2-octyl-1,3-dioxane 
• 259799-86-5 (4R)-4-octyl-1,3,2-dioxathiolane-2-oxide 
• 198561-31-8 (R)-3-hydroxyundecanenitrile 
• 97961-59-6 (S)-3-((1S,3S)-3-Hydroxy-1-methyl-butoxy)-undecanoic acid 
• 4435-85-2 3-oxoundecanoic acid 
• 40165-88-6 3-Hydroxyundecanoic acid 
• 66696-87-5 methyl 3-oxoundecanoate 

Downstream Products

• 40165-88-6 3R-3-hydroxy-undecanoic acid 

Relevant academic research and scientific papers

A fatty acid glycoside from a marine-derived fungus isolated from mangrove plant Scyphiphora hydrophyllacea

To study the antimicrobial components from the endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea Gaertn. F., a new fatty acid glucoside was isolated by column chromatography from the broth of A1, and its structure was identified as R-3-hydroxyundecanoic acid methylester-3- O-α-L- rhamnopyranoside (1) by spectroscopic methods including 1D and 2D NMR (HMQC, 1H-1H COSY and HMBC) and chemical methods. Antimicrobial assay showed compound 1 possessed modest inhibitory effect on Saphylococcus aureus and methicillin-resistant S. aureus (MRSA) using the filter paper disc agar diffusion method.

Enzymatic Regio- And Enantioselective C-H Oxyfunctionalization of Fatty Acids

Directed evolution of a P450 hydroxylase (P450BSβ) achieves an engineered enzyme that is able to catalyze C-H oxyfunctionalization of fatty acids (FAs) in a highly regio- and enantioselective fashion (>20:1 Cβ/Cα and > 99% ee in all cases). The biocatalyst displays high reactivity (TON up to 1540), takes inexpensive H2O2 as oxidant, and converts C11-C18 saturated FAs as well as naturally derived unsaturated oleic and linoleic acids to optically pure β-hydroxy FAs. Merging biocatalysis with chemical transformation, we further offer a chemoenzymatic strategy to access valuable FA derivatives bearing 1,3-diol, β-amino, β-lactone, and β-lactam functionalities in either enantiomeric form. Molecular docking studies provide a rationale for the regio- and enantioselectivity of this reaction.

An efficient method to chiral β-hydroxy acids: Synthesis of lipid-A side chain

The synthesis of optically active β-hydroxy acids 5a-c is achieved in four steps from their corresponding terminal olefins 1a-c by employing Sharpless asymmetric dihydroxylation. The regioselective ring opening of chiral cyclic sulfites 3a-c with cyanide ion, constitutes the key reaction, thus producing the hydroxy nitriles 4a-c.

Resolution and Asymmetric Synthesis of 3-Hydroxycarboxylic Acids by using (-)-Menthone as a Chiral Template

1,3-Dioxan-4-ones 6 and 7 derived from (-)-menthone can be utilized in resolution of 3-hydroxycarboxylic acids and asymmetric synthesis of 2-substituted 3-hydroxycarboxylic acids.

Asymmetric Reduction of Aliphatic Short- to Long-Chain β-Keto Acids by Use of Fermenting Bakers' Yeast

Eleven β-keto acids, ranging from 3-oxobutanoic to 3-oxooctanoic acids, were reduced with fermenting bakers' yeast to the corresponding optically active β-hydroxy acids, which were isolated as the methyl esters.In all cases, the (R)-hydroxy acids were obtained in >/=98percent ee, except for 3-oxobutanoic acid, which afforded the (S)-hydroxy acid in 86percent ee.Inhibition of fermentation was observed for 3-oxoundecanoic to 3-oxotetradecanoic acids, leading to no reduction.Lowering of the substrate concentration was found to be appreciably effective in avoiding inhibition.

ASYMMETRIC SYNTHESIS VIA ACETAL TEMPLATES. 12. HIGHLY DIASTEREOSELECTIVE COUPLING REACTIONS WITH A KETENE ACETAL. AN EFFICIENT, ASYMMETRIC SYNTHESIS OF R-(+)-α-LIPOIC ACID.

TiCl4 catalyzes the essentially quantitative coupling of chiral acetals 1 with 1-t-butoxy-1-t-butyldimethylsilyloxyethene 2 to generate β-alkoxycarboxylates in wich the new asymmetric center is formed with excellent diastereoselection. β-Hydrocarboxylic acids of high ee result from removal of the chiral auxiliary.The procedure has been appllied to the synthesis of R-(+)-α-lipoic acid 10.

The Reaction of Trialkylvinylborate with Carbon Dioxide. A New Method for the Preparation of β-Hydroxycarboxylic Acids from Alkenes

Chloromagnesium trialkylvinylborate, (R3BCH=CH2)MgCl, on reaction with carbon dioxide under pressure, followed by oxidation with alkaline hydrogen peroxide, gives a β-hydroxycarboxylic acid.