44987-72-6

Basic information

• Product Name: (3R)-3-Hydroxyoctanoic acid
• Synonyms: (3R)-3-Hydroxyoctanoic acid;[R,(-)]-3-Hydroxyoctanoic acid
• CAS NO: 44987-72-6
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 0
• Mol File: 44987-72-6.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R)-3-Hydroxyoctanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-3-Hydroxyoctanoic acid(44987-72-6)
• EPA Substance Registry System: (3R)-3-Hydroxyoctanoic acid(44987-72-6)

Safety Data

• Hazardous Substances Data: 44987-72-6(Hazardous Substances Data)

Usage

General Description

(3R)-3-Hydroxyoctanoic acid, also known as (3R)-3-Hydroxyoctanoic acid, is a naturally occurring compound that is of interest in the field of biochemistry and biotechnology. It is a type of hydroxy acid, which means it contains a hydroxyl group attached to a carbon atom in the molecule. (3R)-3-Hydroxyoctanoic acid has potential applications in the production of biodegradable polymers, as well as in the synthesis of pharmaceuticals and other organic compounds. Its stereochemical configuration, represented by the "3R" designation, is also of significance in understanding its properties and potential uses. Overall, (3R)-3-Hydroxyoctanoic acid is a versatile chemical compound with a range of potential applications in various industries.

Upstream product

• 142-61-0 Hexanoyl chloride 
• 13283-91-5 3-oxooctanoic acid 
• 7367-90-0 ethyl β-hydroxyoctanoate 
• 78672-90-9 methyl (R)-(-)-3-hydroxydecanoate 
• 1374979-90-4 (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one 
• 5163-67-7 (E)-oct-3-enoic acid 
• 32556-70-0 (R)-1-octyn-3-ol 
• 10488-95-6 ethyl 3-oxooctanoate 
• 22348-95-4 methyl 3-oxooctanoate 
• 124-07-2 Octanoic acid 
• 118918-31-3 ethyl (-)-(3R)-3-hydroxyoctanoate 
• 133319-86-5 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate 

Downstream Products

• 541-50-4 2-acetoacetic acid 
• 126442-53-3 benzyl (3R)-3-hydroxyoctanoate 
• 7367-87-5 3-hydroxyoctanoic acid methyl ester 
• 192883-14-0 N-(3-hydroxyoctanoyl)-L-homoserine lactone 
• 126442-53-3 (S)-3-hydroxyoctanoic acid benzyl ester 
• 78672-90-9 methyl (R)-(-)-3-hydroxydecanoate 

Relevant articles and documents

Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound

Provided are: a method for producing an aliphatic carboxylic acid compound safely and easily from a starting material that can be obtained or produced industrially without generating a harmful substance such as haloform; and a pyridine compound adduct of an aliphatic ketone compound. The method for producing an aliphatic carboxylic acid compound is a method for producing an aliphatic carboxylic acid compound represented by Formula (I), and comprises: a first step for obtaining a pyridine compound adduct by adding a pyridine compound to an aliphatic ketone compound having an alpha-methyl groupin the presence of an oxidizing agent; and a second step of hydrolyzing the pyridine compound adduct in the presence of a base. In the Formula, R1 represents a substituted or unsubstituted linear alkyl group having 4-8 carbon atoms or a substituted or unsubstituted branched alkyl group having 4-8 carbon atoms; M represents hydrogen, a metal belonging to Group 1 or Group 2 of the periodic table, amethyl group, an ethyl group, an n-propyl group or an isopropyl group.

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

Characterization of FabG and FabI of the Streptomyces coelicolor dissociated fatty acid synthase

Streptomyces coelicolor produces fatty acids for both primary metabolism and for biosynthesis of the secondary metabolite undecylprodiginine. The first and last reductive steps during the chain elongation cycle of fatty acid biosynthesis are catalyzed by FabG and FabI. The S. coelicolor genome sequence has one fabI gene (SCO1814) and three likely fabG genes (SCO1815, SCO1345, and SCO1846). We report the expression, purification, and characterization of the corresponding gene products. Kinetic analyses revealed that all three FabGs and FabI are capable of utilizing both straight and branched-chain β-ketoacyl-NAC and enoyl-NAC substrates, respectively. Furthermore, only SCO1345 differentiates between ACPs from both biosynthetic pathways. The data presented provide the first experimental evidence that SCO1815, SCO1346, and SCO1814 have the catalytic capability to process intermediates in both fatty acid and undecylprodiginine biosynthesis.