D-Erythorbic acid

In apphcations where vitamin C activity is unimportant, often D-erythorbic acid (D-araboascorbic acid) can also be used, providing the same antioxidant and reducing properties as L-ascorbic acid. 

Selective phosphorylation of 5,6-O-isopropylidene D-erythorbic acid (D-erpt/zro-hex-2-enono- 1,4-lactone), the 5-epimer of L-ascorbic acid, was performed with phosphoryl chloride at high pH in the presence of pyridine. D-Erythorbate 2-phosphate (155) is obtained as the crystalline magnesium or cyclohexylammonium salts following removal of the 5,6-acetal.351... 

Araboascorbic acid d-araboascorbic acid D-2,3-didehydro-eryt ro-hexono-l,4-lactone E315 erycorbin d-erythorbic acid D-eryt ro-hex-2-enoic acid D-eryt ro-3-ketohexonic acid lactone glucosaccharonic acid D-isoascorbic acid isovitamin C y-lactone saccharosonic acid. 

L-ascorbic acid (AA) and its isomer D-erythorbic acid (EA) (also called D-isoascorbic acid) have been used as inhibitors of enzymatic browning in fruit and vegetable products for at least 50 years, (15-17). These compounds prevent quinone accumulation and subsequent pigment formation by reducing the 0-quinones generated from the phenolic substrates of PPO back to O-dihydroxyphenolic compounds (17-18). AA also can act as a PPO inhibitor (19-20). AA and EA are used interchangeably although there are indications that AA is more effective in some systems (21-22). 

CAS 89-65-6 EINECS/ELINCS 201-928-0 FEMA 2410 INS315 Synonyms Araboascorbic acid d-Araboascorbic acid D-2,3-Didehydro-erythro-hexono-1,4-lactone Erycorbin d-Erythorbic acid... 

Condensation of dehydro-D-isoascorbic acid (dehydro-D-erythorbic acid) with one or two equivalents of l,2-diamino-4,5-dimethyl-benzene afforded a quinoxalinone, e.g. 81 or a quinoxaline, e.g, 82, respectively. An isomer of flavin adenine dinucleotide containing a D-arabinitol-l-yl rather than a D-ribitol-l-yl moiety, has been identified as a naturally occurring co-factor of the alcohol oxidase of methanol utilizing yeasts. ... 

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. 

D-Araboascorbic acid (erythorbic acid) (10) L-Araboascorbic acid... 

Erythorbic acid is the same compound as D-isoascorbic acid, available from the Aldrich Chemical Company, Inc. This substance is also known as araboascorblc acid. 

L-ascorbic acid (Figure 9-9) is a lactone (internal ester of a hydroxycarboxylic acid) and is characterized by the enediol group, which makes it a strongly reducing compound. The D form has no biological activity. One of the isomers, D-isoascorbic acid, or erythorbic acid, is produced commercially for use as a food additive. L-ascorbic acid is readily and reversibly oxidized to dehydro-L-ascorbic acid (Figure 9-10), which retains vitamin C activity. This compound can be further oxidized to diketo-L-gulonic acid, in a... 

Oxygen scavengers can remove oxygen in a closed system. The most widely used compounds are vitamin C and related substances, ascorbyl palmitate, and erythorbic acid (the D-isomer of ascorbic acid). 

D-lso-ascorbic acid (erythorbic acid see Figure 13.1) also has vitamin activity. in vivo and in cell culmre, it has only about 5% of the biological activity of ascorbate, but this seems to be from poor intestinal absorption and tissue uptake. In vitro with purified enzymes, it has the same cofactor activity as ascorbate. Although it is not a namrally occurring compound, erythorbic acid is widely used interchangeably with ascorbic acid, in cured meats and as an antioxidant in a variety of foods. 

Ascorbic Acid and Ascorbic Acid Esters and Saits Vitamin C or ascorbic acid is widespread in nature but sparingly associated with fats of oils because of its hydrophilic nature (95). Ascorbic acid in the free form, salts of sodium and calcium, and esters of stearic and palmitic are commonly used as antioxidants in foods. Erythorbic acid is the D-isomer of naturally present L-ascorbic acid (Figure 10) and is often used as an antioxidant in dried fruits and a cure... 

Erythorbic acid (or D-ascorbic acid) (Figure 5) is a white or slightly yellow crystalline powder that is often used in fruits and cured meats to enhance curing action and to stabilize the color of food products (34). Unlike its isomer L-ascorbic acid, erythorbic acid is not a natural constituent of foods and has minimal Vitamin C activity (11). 

Erythorbic acid is synthesized by the reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose, and produced from Penicillium spp. 

Synonyms E316 D-eryt/)ro-hex-2-enoic acid sodium salt erythorbic acid sodium salt. 

Isopropylidene-L-ascorbic acid d-Isoascorbic acid (erythorbic)... 

Isopropylidene-D-erythrose has been obtained from 0-arabinose by a route which does not involve the intermediacy of the lactone.All of these processes suffer from either relatively low overall yields or the requirement of a large number of individual stages. The procedure described here, which is based on a similar oxidative degradation of L-ascorbic acid (vitamin C) to L-threonic acid, is undoubtedly the most expeditious route to the acetonide of Q-erythronolactone available. In addition, the starting material, erythorbic acid, is an inexpensive and readily available substance, commonly used as a food preservative. It is pertinent to note that recently L-ascorbic acid has itself found synthetic utility as a precursor to (R)-glycerol acetonide, an Important C3 chiral synthon, ... 

Araboascorbic acid d-Araboascorbic acid. See Erythorbic acid... 

D-2,3-Didehydro-erythro-hexono-1,4-lactone. See Erythorbic acid Didehydromenthane... 

L-Erythritol Erythritol, meso-. See Erythritol D-Erythro-ascorbic acid. See Erythorbic acid Erythroglucin. See Erythritol D-Erythro-hex-2-enonic acid, y-lactone. See Erythorbic acid... 

D-Erythro-hex-2-enonic acid, y-lactone, monosodium salt. See Sodium erythorbate D-Erythro-3-ketohexonic acid lactone. See Erythorbic acid Erythrol. See Erythritol Erythrosin Erythrosin B. See Acid red 51 Erythrosine. See FD C Red No. 3 Acid red 51 Erythrosine bluish. See FD C Red No. 3 Erythrosine yellowish NA. See D C Orange No. 11 Acid red 95... 

Chemistry and mode of action. Ascorbic acid has two asymmetric carbon atoms at C5 and C9 positions. As depicted in Figure 9.11, the naturally occurring ascorbic acid is the L-ascorbic acid form, which is a diastereoisomer of D-isoascorbic acid (erythorbic acid). These diastereo-isomers have similar, but not necessarily the same, physicochemical properties. While ascorbic acid is an accepted additive in Australia, the EC and the USA, erythorbic acid and its sodium salt are not permitted in the EC for winemaking. Ascorbic acid occurs naturally in grapes in amounts between 10 and 100 mg/1, but may be rapidly oxidised after crushing and as a result of the associated aeration. 

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