L-Ascorbic Acid: Properties and Ways of Modification (A Review)

Лавренов, С. Н.; Preobrazhenskaya, M. N.

doi:10.1007/s11094-005-0128-6

Cited by 7 publications

(4 citation statements)

References 62 publications

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“…According to this synthetic approach, also other indole derivatives, such as 1methylascorbigen [6] or 1-N-glucosylascorbigen [26] and a few others [22,27], were accessible. Some synthetic pathways for forming ascorbigen derivatives have also been investigated, starting either from L-ascorbic acid or ascorbigen itself [26,[28][29][30][31][32][33][34][35][36][37]; synthesis of a 14 C-labelled form is also mentioned [38]. In our laboratory, ascorbigen (1) was produced by condensation of 3-indolyl-carbinol (3) with L-ascorbic acid (4) in acidic medium (McIlvaine puffer at pH 4) [49], simulating the conditions of the in planta formation (Fig.…”

Section: Synthesis Of Ascorbigenmentioning

confidence: 99%

Ascorbigen – Occurrence, Synthesis, and Analytics

Opietnik¹,

Jaafar²,

Becker³

et al. 2012

MROC

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Ascorbigen (2-C-(3-indolyl)-methyl--L-xylo-hex-3-ulofuranosono-1,4-lactone, 1) is a breakdown product of glucobrassicins found in cruciferous vegetables, such as cabbage, cauliflower, Brussel sprouts, or broccoli, formed by direct C-alkylation of ascorbic acid (vitamin C) by (3-indolyl)-methyl intermediates under physiological conditions. It is a labile compound, and direct synthesis approaches are hampered by the oxidative instability of the indol moiety and ring transformations of the ascorbyl part. The latter have also impeded ascorbigen analytics for decades, and only recently different ascorbigens have been shown to represent mixtures of compounds rather than individual ascorbigen-type compounds. Following a review of pertinent literature, timely aspects of ascorbigen chemistry, including the most recent synthesis approaches and in-depth characterization of the compound, are presented.

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Section: Synthesis Of Ascorbigenmentioning

confidence: 99%

Ascorbigen – Occurrence, Synthesis, and Analytics

Opietnik¹,

Jaafar²,

Becker³

et al. 2012

MROC

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“…More specifically, the delocalization of π electrons in the molecule and the 2,3-enediol moiety conjugated with the C 1 carbonyl group, make the proton on the C 3 hydroxyl group significantly more acidic (pK 1 = 4.25) than the proton on the C 2 hydroxyl group (pK 2 = 11.57) (Benedini et al, 2011, Kibbe, 2009). The C 2 - and C 3 - OH groups are critical in electron donation and therefore oxidation of AA (Deutsch, 1998, Finholt et al, 1965, Lavrenov and Preobrazhenskaya, 2005).…”

Section: Introductionmentioning

confidence: 99%

3-O-ethyl-l-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin

Iliopoulos¹,

Sil

Moore

et al. 2019

International Journal of Pharmaceutics: X

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“…For anhydrous glycerol, only the glycerol–glycerol interaction should be considered, and for glycerol–water mixtures, the glycerol–glycerol and glycerol–water interaction should be considered. It is known that in in the liquid phase, the three OH groups of the glycerol molecule can be involved in about six hydrogen bonds with of adjacent molecules, while the water molecule can establish four hydrogen bonds; however, water–water interactions were observed in the literature data even at higher glycerol concentrations because of fluctuations in density [ 30 , 31 , 32 , 33 ]. The Plackett–Burman experimental design was used to investigate the compatibility of ascorbic acid with various syrup excipients.…”

Section: Discussionmentioning

confidence: 99%

Assessment of the Influence of the Selected Range of Visible Light Radiation on the Durability of the Gel with Ascorbic Acid and Its Derivative

Golonka

Kizior

Szyja

et al. 2022

IJMS

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(1) Background: Depending on the type of hydrophilic polymer used, different types of hydrogels may be chemically stable or may degrade and eventually disintegrate, or dissolve upon exposure to sunlight. Many over-the-counter medications are now stored with a limited control of temperature, humidity and lighting. Therefore, in this study, the photostability of a gel made of cross-linked polyacrylic acid (PA), methylcellulose (MC) and aristoflex (AV) was assessed, and the interaction between the polymers used and ascorbic acid and its ethylated derivative was investigated. (2) Methods: The samples were continuously irradiated at constant temperature for six hours. The stability of the substance incorporated into the gels was assessed using a UV-Vis spectrophotometer. FTIR-ATR infrared spectroscopy was used to measure changes during the exposure. (3) Results: Ascorbic acid completely decomposed between the first and second hours of illumination in all samples. The exception is the preparation based on polyacrylic acid with glycerol, in which the decomposition of ascorbic acid slowed down significantly. After six hours of irradiation, the ethylated ascorbic acid derivative decomposed in about 5% for the polyacrylic acid-based gels and aristoflex, and in the methylcellulose gel it decomposed to about 2%. In the case of ascorbic acid, the most stable formulation was a gel based on polyacrylic acid and polyacrylic acid with glycerol, and in the case of the ethyl derivative, a gel based on methylcellulose. (4) Conclusions: The experiment showed significant differences in the decomposition rate of both compounds, resulting from their photostability and the polymer used in the hydrogel.

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L-Ascorbic Acid: Properties and Ways of Modification (A Review)

Abstract: Data on the chemical properties of L-ascorbic acid and on the methods used for its modifications are summarized. The pharmaceutical properties of the most important ascorbic acid derivatives and fields of their use are considered.

Cited by 7 publications

References 62 publications

Ascorbigen – Occurrence, Synthesis, and Analytics

Ascorbigen – Occurrence, Synthesis, and Analytics

3-O-ethyl-l-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin

Assessment of the Influence of the Selected Range of Visible Light Radiation on the Durability of the Gel with Ascorbic Acid and Its Derivative

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