16690-38-3

Upstream product

• 124-07-2 Octanoic acid 
• 50-81-7 ascorbic acid 
• 1129294-89-8 isoascorbic acid 
• 111-64-8 n-octanoic acid chloride 
• 111-11-5 methyl octanate 

Relevant academic research and scientific papers

Oxidation kinetics of linoleic acid in the presence of saturated acyl L-ascorbate

The oxidation processes of linoleic acid (LA) in the presence of L-ascorbic acid or saturated acyl L-ascorbate additives were measured at various temperatures and molar ratios of the additive to LA. Higher oxidative stability of LA was observed at higher additive levels for all additives. The addition of the ascorbates lengthened the induction period for the oxidation of LA. An autocatalytic kinetic rate equation was used to model the oxidation processes of LA mixed with the ascorbates, and the dependence of the rate constant, k, on acyl-chain carbon number was determined. At any temperature, the use of ascorbate additives decreased the K value for LA, and there was a slight tendency for K values to decrease with increasing acyl-chain length. The apparent activation energy, Ea, and the frequency factor, k 0, for the rate constant were determined from Arrhenius plots. The calculated Ea and k0 values also decreased with increasing ascorbate acyl-chain length. Copyright

Solubilization of hydrophobic drugs in octanoyl-6-O-ascorbic acid micellar dispersions.

Alkanoyl-6-O-ascorbic acid esters are easily obtained from vitamin C, and produce self-assembled aggregates in water solutions, with an inner hydrophobic pool surrounded by an external hydrophilic shell. Compared to ascorbic acid, their solubility in oils and fats is greatly enhanced, while the peculiar antioxidant activity is retained in the polar head groups of such surfactants. In virtue of their amphiphilic nature, ascorbic acid-based supramolecular systems can dissolve relevant amounts of hydrophobic, poorly water soluble chemicals such as drugs, vitamins, and so on, and at the same time they provide a suitable shield against oxidative deterioration of valuable materials. In this article we report our study on the self-assembling properties of octanoyl-6-O-ascorbic acid in water, and on the solubilization of some lipophilic molecules in its dispersions. Copyright 2002 Wiley-Liss, Inc. and the American Pharmaceutical Association

L-ascorbyl 6-palmitate as lead compound targeting SphK1: an in silico and in vitro investigation

Sphingosine kinases (SphKs) are a class of lipid kinases, that have received extensive attention as important rate-limiting enzyme in tumor. Inhibition of the activity of SphK1 can lead to an anticancer effect. Herein, we describe the discovery process and biological characteristics of a new SphK1 inhibitor, ascorbyl palmitate, discovered through computer-aided drug design. Biochemical experiments show that ascorbyl palmitate has a strong inhibitory effect on SphK1, with an IC50 value of 6.4 μM. The MTT experiment showed that ascorbyl palmitate had anti-cancer effects toward the U87, A549, 22RV1, and A375 cell lines. Among them, ascorbyl palmitate has prominent inhibitory activity against the 22RV1 cell line, with an IC50 value of 41.57 μM. To explore the structure–activity relationship, four ascorbyl palmitate derivatives were synthesized and tested for kinase activity. The outstanding effect of ascorbyl palmitate toward SphK1 and its known non-toxicity suggest that ascorbyl palmitate may be a lead compound for the development of effective SphK1 anti-cancer inhibitors.

A L - ascorbic acid caprylic ester preparation method

The invention relates to a L-ascorbic acid octoate and a preparation method thereof. According to the invention, L-ascorbic acid octoate is dissolved in water, and has oil solubility, anti-oxidizability, emulsibility and bacteriostatic activity. The preparation method is characterized in that n-caprylic acid and L-ascorbic acid octoate are taken as raw materials, immobilized lipase in an organic phase system is used for a catalyzed esterification to synthesize L-ascorbic acid octoate, after the reaction is complete, a reaction solution is performed with steps of filtering, extracting, crystallizing or silica gel column chromatography, and drying under vacuum to obtain L-ascorbic acid octoate. The preparation method takes medium-chain fatty acid n-caprylic acid as a acyl donor, conversion rate being 80-90% can be obtained in a short reaction time, separating purifying is relatively simple, products purity is 95-98%, recovery rate is 75-85%, lipase reuse enables large frequency, enzyme activity can be kept by original 60-75% after 50-80 times of usage, production cost is reduced, and industrial production can be realized.

Lipophilization of ascorbic acid: A monolayer study and biological and antileishmanial activities

Ascorbyl lipophilic derivatives (Asc-C2 to Asc-C18:1) were synthesized in a good yield using lipase from Staphylococcus xylosus produced in our laboratory and immobilized onto silica aerogel. Results showed that esterification had little effect on radical-scavenging capacity of purified ascorbyl esters using DPPH assay in ethanol. However, long chain fatty acid esters displayed higher protection of target lipids from oxidation. Moreover, compared to ascorbic acid, synthesized derivatives exhibited an antibacterial effect. Furthermore, ascorbyl derivatives were evaluated, for the first time, for their antileishmanial effects against visceral (Leishmania infantum) and cutaneous parasites (Leishmania major). Among all the tested compounds, only Asc-C10, Asc-C12, and Asc-C18:1 exhibited antileishmanial activities. The interaction of ascorbyl esters with a phospholipid monolayer showed that only medium and unsaturated long chain (Asc-C10 to Asc-C18:1) derivative esters were found to interact efficiently with mimetic membrane of leishmania. These properties would make ascorbyl derivatives good candidates to be used in cosmetic and pharmaceutical lipophilic formulations.

Effect of the alkyl chains and of the headgroups on the thermal behavior of ascorbic acid surfactants mixtures

The role of the alkyl chain length and of the headgroup on the thermal behavior of mixtures of ASC8 (ascorbyl octanoate) and ASC16 (ascorbyl hexadecanoate) was investigated through differential scanning calorimetry, small- and wide-angle X-ray scattering, and Fourier transform infrared spectroscopy experiments. The formation of two eutectics and of a peritectic point was found from the phase diagram, and their structural properties were studied. The results were compared by investigating the thermal behavior of mixtures of octanoic acid and hexadecanoic acid. The findings provide insights into the role of the ascorbyl headgroups on the intermolecular interactions that determine the phase behavior of the two ascorbic acid based surfactants in the solid state. ? 2014 American Chemical Society.

Cyclopentanone derivatives, method of synthesis and uses thereof

The present invention relates to cyclopentanone derivatives of formula (I), their method of synthesis and uses thereof. Concretely, the compounds disclosed have proved to be inhibitors of glycogen synthase kinase 3β, GSK-3 β, which is known to be involved in different disease and conditions, such as Alzheimer's disease or non-insulin dependent diabetes mellitus. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a GSK-3 mediated disease or condition.

Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases

Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal4755) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal4755, the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 μM for SagHyal4755 and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date.

Coagels from alkanoyl-6-O-ascorbic acid derivatives as drug carriers: Structure and rheology

6-O-Ascorbic acid alkanoates (ASCn, where n is the number of carbon atoms in the alkyl chain) behave as surfactants and form stable supramolecular assemblies in water, depending on chemical structure, concentration and temperature. In concentrated water dispersions, ASCn form liquid crystalline structures ('coagels'), below the critical micellar temperature (CMT), with a typical Krafft phenomenon. Such semisolid systems incorporate and stabilize drugs like anthralin, which is insoluble and unstable in aqueous media. The rheological behavior of coagels obtained from aqueous ASC8, ASC10, ASC11, ASC12, ASC14 and ASC16 was evaluated and related to the coagel structure. For ASC8, ASC12, ASC14 and ASC16 complex rheology was observed and spur values were determined. This behavior is indicative of a high three-dimensional structure. The spur value represents a sharp point of structural breakdown at low shear rate. At this point the semisolids acquire pseudoplastic flow with a very low viscosity. Instead, ASC10 and ASC11 coagels showed pseudoplastic flow and - in the case of ASC11 - thixotropy was observed. The ASCn coagel rheological behavior and their capability to load pharmacologically active compounds point to a potentially valuable capacity for such systems as drug carriers.