617-73-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxycaprylic acid is used as an active pharmaceutical ingredient for its potential therapeutic effects. The hydroxy group in its structure allows for interactions with biopolymers and macromolecules, making it a promising candidate for the development of new drugs.
Used in Cosmetics Industry:
In the cosmetics industry, 2-Hydroxycaprylic acid is used as a moisturizing agent and emulsifier due to its ability to form hydrogen bonds with water molecules and other compounds. This property helps to improve the texture and stability of cosmetic products, providing better skin hydration and a smoother application.
Used in Food Industry:
2-Hydroxycaprylic acid is used as a flavor enhancer and preservative in the food industry. Its unique chemical structure allows it to interact with taste receptors, enhancing the overall flavor profile of various food products. Additionally, its antimicrobial properties help to extend the shelf life of perishable items.
Used in Chemical Synthesis:
2-Hydroxycaprylic acid serves as a key intermediate in the synthesis of various chemicals and materials. Its hydroxy group can be further modified or reacted with other compounds to produce a wide range of products, such as surfactants, polymers, and specialty chemicals, which find applications in various industries.

Purification Methods

Crystallise the acid from EtOH/pet ether or ether/ligroin. [Beilstein 3 IV 873.]

InChI:InChI=1/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)

Upstream product

• 124-07-2 Octanoic acid 
• 93168-18-4 2-hydroxyoctanoic acid ethyl ester 
• 90113-62-5 (+/-)-Hex-2-enyl-hydroxy-essigsaeure 
• 328-51-8 2-oxooctanoic acid 
• 28870-09-9 2-hydroxy-octanoic acid amide 
• 204381-90-8 1,1-Diiodo-octan-2-ol 
• 127-09-3 sodium acetate 
• 151-50-8 potassium cyanide 
• 42512-94-7 α-Acetoxy-caprylsaeure-ethylester 
• 64713-78-6 1,1,1-trichloro-octan-2-ol 
• 106-32-1 octanoic acid ethyl ester 
• 126543-34-8 ((Z)-1-Ethoxy-oct-1-enyloxy)-trimethyl-silane 
• 111-71-7 heptanal 
• 106-73-0 methyl heptanoate 

Downstream Products

• 111-71-7 heptanal 
• 73634-76-1 2-hydroxyoctanoic acid methyl ester 
• 328-51-8 2-oxooctanoic acid 
• 95513-13-6 benzyl 2-hydroxyoctanoate 
• 64-18-6 formic acid 
• 111-14-8 oenanthic acid 
• 15719-64-9 methylammonium carbonate 
• 124-38-9 carbon dioxide 
• 144-62-7 oxalic acid 
• 142-62-1 hexanoic acid 
• 724784-48-9 methyl (4R)-4-[(2-hydroxyoctanoyl)amino]-5-phenylpentanoate 
• 779355-47-4 3-methyl-6-hexyl-1,4-dioxane-2,5-dione 
• 95513-14-7 benzyl 2-(<(trifluoromethyl)sulfonyl>oxy)octanoate 
• 129454-53-1 2-Benzyloxy-octan-1-ol 

Relevant academic research and scientific papers

Synthesis and properties of novel poly(hexyl-substituted lactides) for pharmaceutical applications

Monohexyl-substituted lactide (mHLA) was synthesized by reaction of 2-hydroxyoctanoic acid with 2-bromopropionyl bromide, and polymerized with tin(II) 2-ethylhexanoate (Sn(Oct)2) or 4-dimethylaminopyridine (DMAP) in the presence of benzyl alcohol by ring-opening polymerization (ROP). Poly(monohexyl-substituted lactide) (Pm-HLA) of predictable molecular weights and narrow polydispersities were obtained in convenient bulk conditions at 100°C within short polymerization times. The polymerizations were well controlled, showing a 'living' character for targeted degrees of polymerization up to DP = 60 as evidenced by molecular weight versus conversion studies and 1H NMR end group analysis. The hexyl groups have a strong impact on the glass transition temperature (Tg), which is low for PmHLA compared to standard poly(D,L-lactide) (PLA). Tg and zero shear viscosities at 25°C can be controlled by the polymer molecular weight, ranging from -22°C for Mn = 2800 g/mol to -10°C for M n = 9100 g/mol and 140 to 4850 Pa.s, respectively. These data are in correspondence with the Fox and Flory equations. The degradation mechanism of the PmHLA polymer in phosphate buffer pH 7.4 at 37°C was shown to be similar to that of the standard PLA ('bulk erosion' type), with a slightly higher degradation rate, leading to the non-toxic degradation products lactic acid and 2-hydroxyoctanoic acid. PmHLA has the great potential as an alternative to conventional PLA/PLGA for drug delivery systems. By the hexyl-substitution the biodegradable PLA-ester backbone is conserved but the hydrophobicity is increased in comparison to standard PLA, while a viscous polymer is obtained. This leads to advantageous injectable solvent-free drug delivery systems, in which drugs can easily be incorporated by simple mixing. Schweizerische Chemische Gesellschaft.

P450Jα: A New, Robust and α-Selective Fatty Acid Hydroxylase Displaying Unexpected 1-Alkene Formation

Oxyfunctionalization of fatty acids (FAs) is a key step in the design of novel synthetic pathways for biobased/biodegradable polymers, surfactants and fuels. Here, we show the isolation and characterization of a robust FA α-hydroxylase (P450Jα) which catalyses the selective conversion of a broad range of FAs (C6:0-C16:0) and oleic acid (C18:1) with H2O2 as oxidant. Under optimized reaction conditions P450Jα yields α-hydroxy acids all with >95 % regioselectivity, high specific activity (up to 15.2 U mg?1) and efficient coupling of oxidant to product (up to 85 %). Lauric acid (C12:0) turned out to be an excellent substrate with respect to productivity (TON=394 min?1). On preparative scale, conversion of C12:0 reached 83 % (0.9 g L?1) when supplementing H2O2 in fed-batch mode. Under similar conditions P450Jα allowed further the first biocatalytic α-hydroxylation of oleic acid (88 % conversion on 100 mL scale) at high selectivity and in good yields (1.1 g L?1; 79 % isolated yield). Unexpectedly, P450Jα displayed also 1-alkene formation from shorter chain FAs (≤C10:0) showing that oxidative decarboxylation is more widely distributed across this enzyme family than reported previously.

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.

Preparative Asymmetric Synthesis of Canonical and Non-canonical α-amino Acids Through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids

Chemical and biocatalytic synthesis of non-canonical α-amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three-step, scalable and modular one-pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure l-α-amino acids. In module 1, selective α-hydroxylation of FAs is catalyzed by the P450 peroxygenase P450CLA. By using an automated H2O2 supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable α-hydroxy acids (α-HAs; >90% α-selective) is shown on preparative scale (up to 2.3 g L?1 isolated product). In module 2, a redox-neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of α-HAs into l-α-AAs (20 to 99%). Enantiopure l-α-AAs (e.e. >99%) including the pharma synthon l-homo-phenylalanine can be obtained at product titers of up to 2.5 g L?1. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs. (Figure presented.).

Preparative Asymmetric Synthesis of Canonical and Non-canonical a-amino Acids through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids

Chemical and biocatalytic synthesis of non-canonical a-amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three-step, scalable and modular one-pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure l-a-amino acids. In module 1, selective a-hydroxylation of FAs is catalyzed by the P450 peroxygenase P450CLA. By using an automated H2O2 supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable a-hydroxy acids (a-HAs; >90% a-selective) is shown on preparative scale (up to 2.3 gL1 isolated product). In module 2, a redox-neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of a-HAs into l-a-AAs (20 to 99%). Enantiopure l-a-AAs (e.e. >99%) including the pharma synthon l-homo-phenylalanine can be obtained at product titers of up to 2.5 gL1. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs.

2 - hydroxyalkyl acids prepared from a polymer composition comprising

PROBLEM TO BE SOLVED: To provide compositions comprising polymers prepared by melt polycondensation of 2-hydroxyalkyl acids, in particular pharmaceutical compositions, and methods of preparing the compositions.SOLUTION: The composition comprises a releasable chemical substance, and one or more polymer of one or more substituted or unsubstituted C-C2-hydroxyalkyl acid, the polymer prepared by melt polycondensation.

Compositions comprising polymers prepared from 2-hydroxyalkyl acids

Described herein are compositions comprising polymers prepared by melt polycondensation of 2-hydroxyalkyl acids. Methods of making and using the compositions are also disclosed.

2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry

The development of 2-isocyanopyridines as novel convertible isocyanides for multicomponent chemistry is reported. Comparison of 12 representatives of this class revealed 2-bromo-6-isocyanopyridine as the optimal reagent in terms of stability and synthetic efficiency. It combines sufficient nucleophilicity with good leaving group capacity of the resulting amide moiety under both basic and acidic conditions. To demonstrate the practical utility of this reagent, an efficient two-step synthesis of the potent opioid carfentanil is presented.

A chemoselective oxidation of monosubstituted ethylene glycol: Facile synthesis of optically active α-hydroxy acids

A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variety of aliphatic, aromatic and carbohydrate substrates bearing various functional groups. the Partner Organisations 2014.

COMPOSITIONS COMPRISING POLYMERS PREPARED FROM 2-HYDROXYALKYL ACIDS

Described herein are compositions comprising polymers prepared by melt polycondensation of 2-hydroxyalkyl acids. Methods of making and using the compositions are also disclosed.