56472-29-8

Usage

Uses

Used in Anticancer Applications:
2-HYDROXYOLEICACID is used as an anticancer agent for its effectiveness against various types of cancer. It serves as a modulator of the sphingolipid and glycerophospholipid pathways, which are crucial in the development and progression of cancer cells.
Used in Cardiovascular Applications:
2-HYDROXYOLEICACID is used as an antihypertensive agent, helping to regulate blood pressure and maintain a healthy cardiovascular system.
Used in Biomedical Research:
2-HYDROXYOLEICACID is used as a modulator in the study of myelination in mice Charcot–Marie–Tooth type 1A (CMT1A) myelinopathy and myelinating dorsal root ganglia cultures. This application aids in understanding the role of the compound in nerve regeneration and repair.
Used in Biophysical Studies:
2-HYDROXYOLEICACID is used in biophysical studies to investigate its effects on artificial membranes and its interactions with major membrane lipid films. This research contributes to the understanding of the compound's role in cellular processes and its potential applications in drug delivery systems and other therapeutic approaches.

Biochem/physiol Actions

2-Hydroxy oleic acid (2OHOA) is a derivative of oleic acid. It plays a role in membrane organization, alterations in?membrane fluidity, an increase of the tendency to form non-lamellar structures, and remodeling of microdomains by interacting with the lipids in membranes of pathological cells.

Upstream product

• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 23433-07-0 (R)-nonane-1,3-diol 
• 7432-41-9 8(Z)-heptadecenoic acid 

Relevant academic research and scientific papers

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 THE SYNTHESIS OF HYDROXY-TRIGLYCERIDES AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF DISEASES

The present invention relates to hydroxy-triglycerides, their synthesis, a pharmaceutical and/or nutraceutical composition which comprises at least one of said hydroxy- triglycerides, and a method which comprises the administration to a patient of a therapeutically effective quantity of at least one of said hydroxy-triglycerides or at least one of said pharmaceutical and/or nutraceutical compositions, for the prevention and/or treatment of at least one disease selected from cancer, metabolic/cardio vascular diseases, and/or neurological/inflammatory diseases.

Synthesis of optically active α-hydroxy acids by kinetic resolution through lipase-catalyzed enantioselective acetylation

The lipase-catalyzed acetylation of a broad spectrum of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candida antarctica and Burkholderia species, are convenient biocatalysts for the synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to 99%). The absolute configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3. These results establish that (S)-2-hydroxy acids 1 were preferentially acetylated by microbial lipases.