Of ascorbic acid

Sorbitol is manufactured by the reduction of glucose in aqueous solution using hydrogen with a nickel catalyst. It is used in the manufacture of ascorbic acid (vitamin C), various surface active agents, foodstuffs, pharmaceuticals, cosmetics, dentifrices, adhesives, polyurethane foams, etc. 

Akkermans R P, Wu M, Bain C D, Fidel-Suerez M and Compton R G 1998 Electroanalysis of ascorbic acid a comparative study of laser ablation voltammetry and sonovoltammetry E/eofroana/ys/s 10 613... 

Since allylation with allylic carbonates proceeds under mild neutral conditions, neutral allylation has a wide application to alkylation of labile compounds which are sensitive to acids or bases. As a typical example, successful C-allylation of the rather sensitive molecule of ascorbic acid (225) to give 226 is possible only with allyl carbonate[l 37]. Similarly, Meldrum s acid is allylated smoothly[138]. Pd-catalyzed reaction of carbon nucleophiles with isopropyl 2-methylene-3,5-dioxahexylcarbomite (227)[I39] followed by hydrolysis is a good method for acetonylation of carbon nucleophiles. 

The content of ascorbic acid, in milligrams per 100 mL, in orange juice is determined by a redox titration using either 2,6-dichlorophenolindephenol or N-bromosuccinimide as the titrant. 

The titration of ascorbic acid using coulometrically generated I2 and Br2 is described in this experiment. Details are also given for the polarographic analysis of ascorbic acid. 

The technique of hydrodynamic modulation voltammetry (HMV), in which the rate of stirring is pulsed between high and low values, is demonstrated in this experiment. The application of HMV for the quantitative analysis of ascorbic acid in vitamin C tablets using the method of standard additions also is outlined. 

Procedure. Samples are collected in 40-mL vials with screw-caps lined with a Teflon septum. Fill the vial to overflowing, ensuring that there are no air bubbles. Add a reducing agent of ascorbic acid (25 mg/40 mL) to quench the further production of trihalomethanes, and seal the vial. Store samples at 4 °C, and analyze within 14 days. 

This experiment describes the use of FIA for determining the stoichiometry of the Fe +-o-phenanthroline complex using the method of continuous variations and the mole-ratio method. Directions are also provided for determining the stoichiometry of the oxidation of ascorbic acid by dichromate and for determining the rate constant for the reaction at different pH levels and different concentration ratios of the reactants. 

Food process optimi2ation measurements may link a single chemical such as a vitamin, or a physical change such as viscosity, to process conditions and to consumer acceptance. Retention levels of ascorbic acid [50-81-7] C HgO, or thiamine can often be used as an indicator of process conditions (see... 

Of the water-soluble vitamins, intakes of nicotinic acid [59-67-6] on the order of 10 to 30 times the recommended daily allowance (RE)A) have been shown to cause flushing, headache, nausea, and moderate lowering of semm cholesterol with concurrent increases in semm glucose. Toxic levels of foHc acid [59-30-3] are ca 20 mg/d in infants, and probably approach 400 mg/d in adults. The body seems able to tolerate very large intakes of ascorbic acid [50-81-7] (vitamin C) without iH effect, but levels in excess of 9 g/d have been reported to cause increases in urinary oxaHc acid excretion. Urinary and blood uric acid also rise as a result of high intakes of ascorbic acid, and these factors may increase the tendency for formation of kidney or bladder stones. AH other water-soluble vitamins possess an even wider margin of safety and present no practical problem (82). 

As a result of having two chiral centers, four stereoisomers of ascorbic acid are possible (Table 1) (Fig. 2). Besides L-ascorbic acid (Activity = 1), only D-araboascorbic acid (erythorbic acid (9)) shows vitamin C activity (Activity = 0.025-0.05). The L-ascorbic acid stmcture (1) in solution and the soHd state are almost identical. Ascorbic acid crystallizes in the space group P2 with four molecules in the unit cell. The crystal data are summarized in Table 2. 

Stability. Ascorbic acid, a white crystalline compound, is very soluble ia water and has a sharp, acidic taste. In solution, the vitamin oxidizes on exposure to air, light, and elevated temperatures. Solutions of ascorbic acid turn yellowish, followed by development of a tan color. Ascorbic acid is stable to air when dry but gradually darkens on exposure to light. 

Chemical Synthesis. The first synthesis of ascorbic acid was reported ia 1933 by Reichsteia and co-workers (14,39—42) (Fig. 4). Similar, iadependent reports pubHshed by Haworth and co-workers followed shordy after this work (13,43—45). L-Xylose (16) was converted by way of its osazone (17) iato L-xylosone (18), which reacted with hydrogen cyanide forming L-xylonitfile (19). L-Xylonitfile cyclized under mild conditions to the cycloimine of L-ascorbic acid. Hydrolysis of the cycloimine yielded L-ascorbic acid. The yield for the conversion of L-xylosone to L-ascorbic acid was ca 40%. 

Fermentation. Much time and effort has been spent in undertaking to find fermentation processes for vitamin C (47). One such approach is now practiced on an industrial scale, primarily in China. It is not certain, however, whether these processes will ultimately supplant the optimized Reichstein synthesis. One important problem is the instabiUty of ascorbic acid in water in the presence of oxygen it is thus highly unlikely that direct fermentation to ascorbic acid will be economically viable. The successful approaches to date involve fermentative preparation of an intermediate, which is then converted chemically to ascorbic acid. 

Because of the time and expense involved, biological assays are used primarily for research purposes. The first chemical method for assaying L-ascorbic acid was the titration with 2,6-dichlorophenolindophenol solution (76). This method is not appHcable in the presence of a variety of interfering substances, eg, reduced metal ions, sulfites, tannins, or colored dyes. This 2,6-dichlorophenolindophenol method and other chemical and physiochemical methods are based on the reducing character of L-ascorbic acid (77). Colorimetric reactions with metal ions as weU as other redox systems, eg, potassium hexacyanoferrate(III), methylene blue, chloramine, etc, have been used for the assay, but they are unspecific because of interferences from a large number of reducing substances contained in foods and natural products (78). These methods have been used extensively in fish research (79). A specific photometric method for the assay of vitamin C in biological samples is based on the oxidation of ascorbic acid to dehydroascorbic acid with 2,4-dinitrophenylhydrazine (80). In the microfluorometric method, ascorbic acid is oxidized to dehydroascorbic acid in the presence of charcoal. The oxidized form is reacted with o-phenylenediamine to produce a fluorescent compound that is detected with an excitation maximum of ca 350 nm and an emission maximum of ca 430 nm (81). 

Chromatographic methods, notably hplc, are available for the simultaneous deterrnination of ascorbic acid as weU as dehydroascorbic acid. Some of these methods result in the separation of ascorbic acid from its isomers, eg, erythorbic acid and oxidation products such as diketogulonic acid. Detection has been by fluorescence, uv absorption, or electrochemical methods (83—85). Polarographic methods have been used because of their accuracy and their ease of operation. Ion exclusion (86) and ion suppression (87) chromatography methods have recently been reported. Other methods for ascorbic acid deterrnination include enzymatic, spectroscopic, paper, thin layer, and gas chromatographic methods. ExceUent reviews of these methods have been pubHshed (73,88,89). 

L-Tyrosine metabohsm and catecholamine biosynthesis occur largely in the brain, central nervous tissue, and endocrine system, which have large pools of L-ascorbic acid (128). Catecholamine, a neurotransmitter, is the precursor in the formation of dopamine, which is converted to noradrenaline and adrenaline. The precise role of ascorbic acid has not been completely understood. Ascorbic acid has important biochemical functions with various hydroxylase enzymes in steroid, dmg, andhpid metabohsm. The cytochrome P-450 oxidase catalyzes the conversion of cholesterol to bUe acids and the detoxification process of aromatic dmgs and other xenobiotics, eg, carcinogens, poUutants, and pesticides, in the body (129). The effects of L-ascorbic acid on histamine metabohsm related to scurvy and anaphylactic shock have been investigated (130). Another ceUular reaction involving ascorbic acid is the conversion of folate to tetrahydrofolate. Ascorbic acid has many biochemical functions which affect the immune system of the body (131). 

Iron Absorption. A very important effect of ascorbic acid is the enhancement of absorption of nonheme iron from foods. Ascorbic acid also enhances the reduction of ferric iron to ferrous iron. This is important both in increasing iron absorption and in its function in many hydroxylation reactions (140,141). In addition, ascorbic acid is involved in iron metaboHsm. It serves to transfer iron to the Hver and to incorporate it into ferritin. 

Up to 80% of oral doses of ascorbic acid are absorbed in humans with intakes of less than 0.2 g of vitamin C. Absorption of pharmacological doses ranging from 0.2 g to 12 g results in an inverse relationship, with less than 20% absorption at the higher doses. A single oral dose of 3 g has been reported to approach the absorptive capacity (tissue saturation) of the human intestine. Higher blood levels can be attained by providing multiple divided vitamin C doses per day. 

The adrenal glands and pituitary glands have the highest tissue concentration of ascorbic acid. The brain, Hver, and spleen, however, represent the largest contribution to the body pool. Plasma and leukocyte ascorbic acid levels decrease with increasing age (152). Elderly people require higher ascorbic acid intakes than children to reach the same plasma and tissue concentration (153). 

Mobilization and Metabolism. The total ascorbic acid body pool in healthy adults has been estimated to be approximately 1.5 g, which increases to 2.3—2.8 g with intakes of 200 mg/d (151—158). Depletion of the body pool to 600 mg initiates physiological changes, and signs of clinical scurvy are reported when the body pool falls below 300 mg (149). Approximately 3—4% of the body pool turns over daily, representing 40—60 mg/d of metabolized, or consumed, vitamin C. Smokers have a higher metaboHc turnover rate of vitamin C (approximately 100 mg/d) and a lower body pool than nonsmokers, unless compensated through increased daily intakes of vitamin C (159). The metaboHsm of ascorbic acid varies among different species. 

The half-life of ascorbic acid is inversely related to the daily intake and is 13—40 d in humans and 3 d in guinea pigs, which is consistent with the longer time for humans to develop scurvy. 

Many reactions catalyzed by the addition of simple metal ions involve chelation of the metal. The familiar autocatalysis of the oxidation of oxalate by permanganate results from the chelation of the oxalate and Mn (III) from the permanganate. Oxidation of ascorbic acid [50-81-7] C HgO, is catalyzed by copper (12). The stabilization of preparations containing ascorbic acid by the addition of a chelant appears to be negative catalysis of the oxidation but results from the sequestration of the copper. Many such inhibitions are the result of sequestration. Catalysis by chelation of metal ions with a reactant is usually accomphshed by polarization of the molecule, faciUtation of electron transfer by the metal, or orientation of reactants. 

The calcium form of EDTA instead of free EDTA is used in many food preparations to stabilize against such deleterious effects as rancidity, loss of ascorbic acid, loss of flavor, development of cloudiness, and discoloration. The causative metal ions are sequestered by displacing calcium from the chelate, and possible problems, such as depletion of body calcium from ingestion of any excess of the free chelant, had it been used, are avoided. 

Two techniques for sorption-spectroscopic determination of ascorbic acid have been proposed. The first one is the recovery by silica modified with tetradecyl ammonium nitrate of blue form of molibdophosphoric HPA in the presence of vitamin C. And the second one is the interaction between the ascorbic acid in solution and immobilized on silica ion associate of molibdophosphoric acid with lucigenine. The detection limits of vitamin C are 0.07 and 2.6 mg respectively. The techniques were successfully applied to the determination of ascorbic acid in fmit juices. 

INDIRECT DETERMINATION OF ASCORBIC ACID BY ELECTROTHERMAL ATOMIC ABSORPTION SPECTROMETRY... 

Ascorbic acid commonly known as vitamin C, is one of the most important water soluble vitamins. Ascorbic acid is involved in many biological processes and it is an essential compound in the human diet [1]. The determination of ascorbic acid has gained increase significance in pharmaceutic, clinical, and food applications. So far, different methods have been developed for determination of ascorbic acid [2, 3]. 

In this work, a method based on the reduction potential of ascorbic acid was developed for the sensitive detennination of trace of this compound. In this method ascorbic acid was added on the Cr(VI) solution to reduced that to Cr(III). Cr(III) produced in solution was quantitatively separated from the remainder of Cr(VI). The conditions were optimized for efficient extraction of Cr(III). The extracted Cr(III) was finally mineralized with nitric acid and sensitively analyzed by electro-thermal atomic absorption spectrometry. The determinations were carried out on a Varian AA-220 atomic absolution equipped with a GTA-110 graphite atomizer. The results obtained by this method were compared with those obtained by the other reported methods and it was cleared that the proposed method is more precise and able to determine the trace of ascorbic acid. Table shows the results obtained from the determination of ascorbic acid in two real samples by the proposed method and the spectrometric method based on reduction of Fe(III). 

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