Self-Assembly and Antioxidant Properties of Octanoyl-6-O-ascorbic Acid

Nostro, Pierandrea Lo; Capuzzi, Giulia; Romani, and Annalisa; Mulinacci, Nádia

doi:10.1021/la990796j

Cited by 56 publications

(76 citation statements)

References 34 publications

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“…Lo Nostro et al first demonstrated the ability of ampiphilic ascorbic acid esters to self aggregate and form micellar structures in an aqueous media [17]. The nanocarriers retained the antioxidant activity due to the presence of ascorbyl moiety in the polar head group, while the inner micellar provides a hydrophobic core.…”

Section: Introductionmentioning

confidence: 99%

Ascorbyl palmitate/DSPE-PEG nanocarriers for oral iron delivery: Preparation, characterisation and in vitro evaluation

Zariwala

Farnaud

Merchant

et al. 2014

Colloids and Surfaces B: Biointerfaces

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Section: Introductionmentioning

confidence: 99%

Ascorbyl palmitate/DSPE-PEG nanocarriers for oral iron delivery: Preparation, characterisation and in vitro evaluation

Zariwala

Farnaud

Merchant

et al. 2014

Colloids and Surfaces B: Biointerfaces

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“…The reducing activity of vitamin C, its ester derivatives and various commercially available natural antioxidants were determined and compared (Figure 3) [5]. This study shows that ascorbyl esters are high potential antioxidants with radical scavenging capability.…”

Section: Antioxidant and Pharmaceutical Uses Of Ascorbyl Estersmentioning

confidence: 99%

The synthesis, properties, and applications of ascorbyl esters

Karmee

2011

Lipid Technology

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Ascorbic acid is a naturally occurring antioxidant. Nevertheless, its primary applications as an antioxidant in the life science, food and pharmaceutical industries are limited because of its hydrophilic nature. Alternatively, ascorbyl acid esters are potential surfactants and antioxidants. Chemical methods for the synthesis of ascorbyl esters lead to the formation of side products and simultaneous decomposition of ascorbic acid due to harsh reaction conditions. In contrast, lipases are used as regioselective and mild catalysts for the synthesis of ascorbyl esters. So far, various acyl donors namely, fatty acids, fatty acid alkyl esters, fatty acid vinyl esters and triacylglycerols have been explored for the synthesis of ascorbyl fatty esters. Other compounds such as L-methyl lactate, bixin, phenyl butyric acid are also used as acyl donors. This article is focused on the recent developments of lipase-catalyzed synthesis of ascorbyl esters, their antioxidant properties and applications.

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“…15) From the assumption that the micellar solution of the molar ratio of 5 was composed of the 1 : 2 complex of N-4472 and VC with the molecular weight of 930, the association number of the 1 : 2 complex was anticipated to be 15 from the weight-average molecular weight (14000), being consistent with the result reported by Schreier et al Nostro et al investigated the surface active properties of VC derivatives (ASC 8, ASC 10, ASC 12) which were C 8, C 10 and C 12 esters of VC, they reported that all VC derivatives had surface active properties which were due to their amphiphilic structure comprising both hydrophilic VC moiety and hydrophobic alkyl chain. 16) They also reported that ASC 8 with the shortest alkyl chain was freely soluble in water through micelle formation, whereas ASC 10 and ASC 12, the hydrophobic moiety consisting of longer alkyl chains, showed low aqueous solubility and no micelle formation. 16) These results could be attributable to the difference in the hydrophilic-hydrophobic balance (HLB) values of the amphiphilic VC derivatives.…”

Section: )mentioning

confidence: 99%

“…16) They also reported that ASC 8 with the shortest alkyl chain was freely soluble in water through micelle formation, whereas ASC 10 and ASC 12, the hydrophobic moiety consisting of longer alkyl chains, showed low aqueous solubility and no micelle formation. 16) These results could be attributable to the difference in the hydrophilic-hydrophobic balance (HLB) values of the amphiphilic VC derivatives. As shown in Fig.…”

Section: )mentioning

confidence: 99%

Improvement of Physicochemical Properties of N-4472. Part III. VC/N-4472 Complex Formation and Self-association in Aqueous Solution.

Itoh

Tozuka

Oguchi

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Formation of the counter-ion salt characteristic of higher dissociation constant is one of the promising procedures extensively employed to improve the aqueous solubility of ionic but poorly water-soluble drugs.1) However, it has been reported that the crystal lattice energy varied even in the crystalline salts formed with the same drug depending on kinds of the applied counter ions, leading to different physicochemical properties in the solid state including apparent solubility and dissolution rate, eventually resulting in difference in the oral absorption rate.2) From the comparison of the aqueous solubility of both nicardipine phosphate and nicardipine hydrochloride, Michael et al. reported that approximately 10-fold difference in the solubility was observed between them due to successful solubilization of nicardipine phosphate attributable to self-association and micelle formation in the aqueous solution.3) These findings suggest that difference of the applied counter ions remarkably affected not only the solubility of the salt but also solubilizing behaviors in the aqueous solution. As a consequence, selection of the most appropriate counter ion is significantly outweighed upon the salt formation.Diphenylmethane derivatives as anti-histamine agents 4) and phenothiazine derivatives as psychotropic agents 5,6) were solubilized due to intrinsic self-association in aqueous solution. These drugs had common characteristic that the molecules possessed amphiphilic structures comprising both hydrophilic and hydrophobic moieties.N- [2][3]) is a newly developed drug having a lipid-lowering effect. With its aqueous solubility of less than 0.2 mg/ml (solubility in JP XIV 2nd fluid and distilled water at 37°C), this drug has a drawback to be poorly absorbed after oral administration. In the present study, with an aim to improve the aqueous solubility of N-4472 (solubility in JP XIV 1st fluid at 37°C: 44 mg/ml, pK a : 7.9), we investigated aqueous solubilizing behavior and mechanism of the evaporates of N-4472 which were prepared by addition of various organic acids.

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Self-Assembly and Antioxidant Properties of Octanoyl-6-O-ascorbic Acid

Cited by 56 publications

References 34 publications

Ascorbyl palmitate/DSPE-PEG nanocarriers for oral iron delivery: Preparation, characterisation and in vitro evaluation

Ascorbyl palmitate/DSPE-PEG nanocarriers for oral iron delivery: Preparation, characterisation and in vitro evaluation

The synthesis, properties, and applications of ascorbyl esters

Improvement of Physicochemical Properties of N-4472. Part III. VC/N-4472 Complex Formation and Self-association in Aqueous Solution.

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