ISOASCORBIC ACID
ISOASCORBIC ACID
Isoascorbic acid = Erythorbic acid = D-Isoascorbic acid = D-arabo ascorbic acid = E315
CAS Number: 89-65-6
Molecular Weight: 176.12
EINECS, EC No.: 201-928-0
HS Code: 2932290090
Molecular formula: C6H8O6
Molecular weight: 176.13 g/mol
Isoascorbic acid is applied as an antioxidant in the food industry.
Isoascorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer of ascorbic acid (vitamin C).
Isoascorbic acid is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide.
Isoascorbic acid can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature.
Isoascorbic acid is denoted by E number E315, and is widely used as an antioxidant in processed foods.
Clinical trials have been conducted to investigate aspects of the nutritional value of Isoascorbic acid.
One such trial investigated the effects of Isoascorbic acid on vitamin C metabolism in young women; no effect on vitamin C uptake or clearance from the body was found.
Since the U.S. Food and Drug Administration banned the use of sulfites as a preservative in foods intended to be eaten fresh (such as salad bar ingredients), the use of Isoascorbic acid as a food preservative has increased.
Isoascorbic acid is also used as a preservative in cured meats and frozen vegetables.
Functions and Applications of Isoascorbic acid:
-Isoascorbic acid is produced in acidic condition by sodium erythorbate.
-Isoascorbic acid has strong reducing action and has effects on reducing blood press, diuresis,generationg liver glycogen,excreting pigment,detoxifying the body.
-Isoascorbic acid is non-toxic.
Isoascorbic acids other applications are familiar to sodium erythorbate.
Sodium erythorbateand Isoascorbic acid are generally recognized as the lastest A-class Green products internationally and have become the commodities in short supply both at home and abroad.
Isoascorbic acid is a potent enhancer of iron absorption, Isoascorbic acids lack of antiscorbutic activity limits its usefulness in iron-fortification programs.
Isoascorbic acid may play a major role in enhancing iron bioavailability from mixed diets that include foods preserved with Isoascorbic acid.
What Is Isoascorbic acid E315?
Isoascorbic acid E315 is used as food antioxidant.
The applications of Isoascorbic acid in creams, cheeses, dairy-based drinks, dairy-based desserts, spreads, vegetables, processed fruit, confectionery, pastas, meats, seasonings, cereals, condiments, broths, soups, sauces, wines, beer and malt beverages, and water-based flavoured drinks.
Ascorbyl Palmitate and Ascorbyl Dipalmitate are produced from ascorbic acid, or vitamin C, and palmitic Acid, a fatty acid obtained from animal and vegetable fats and oils.
Ascorbyl Palmitate has vitamin C activity approximately equal to that of Ascorbic Acid (L-form).
Ascorbyl Stearate is produced from ascorbic acid, and stearic acid, another fatty acid obtained from animal and vegetable fats and oils.
Isoascorbic acid is an isomer of ascorbic acid.
In foods, Ascorbyl Palmitate is used as a source of vitamin C for meat curing and to preserve canned and frozen foods.
Isoascorbic acid also prevents the browning of cut apples.
Chemical Properties of Isoascorbic acid:
Isoascorbic acid occurs as a white or slightly yellow-colored crystals or powder.
Isoascorbic acid gradually darkens in color upon exposure to light.
Uses of Isoascorbic acid:
Isoascorbic acid used as Antioxidant (industrial and food), especially in brewing industry, reducing agent in photography.
Isoascorbic acid is a food preservative that is a strong reducing agent (oxygen accepting) which functions similarly to antioxidants.
In the dry crystalline state Isoascorbic acid is nonreactive, but in water solutions it reacts readily with atmospheric oxygen and other oxidizing agents, making it valuable as an antioxidant.
During preparation, dissolving and mixing should incorporate a minimum amount of air, and storage should be at cool temperatures.
Isoascorbic acid has a solubility of 43 g/100 ml of water at 25°c. One part is equivalent to one part ascorbic acid and equivalent to one part sodium erythorbate.
Isoascorbic acid is used to control oxidative color and flavor deterioration in fruits at 150–200 ppm.
Isoascorbic acid is used in meat curing to speed and control the nitrite curing reaction and prolong the color of cured meat at levels of 0.05%.
Production Methods of Isoascorbic acid:
Isoascorbic acid is synthesized by the reaction between methyl 2- keto-D-gluconate and sodium methoxide.
Isoascorbic acid can also be synthesized from sucrose, and produced from Penicillium spp.
Biotechnological Production of Isoascorbic acid:
Yeasts and other fungi synthesize the C5 sugar acid D-erythroascorbic acid which shares structural and physicochemical properties with Asc.
D-erythroascorbic acid serves similar protective functions in these microorganisms as Asc does in plants and animals, including the scavenging of reactive oxygen species.
The biosynthesis of D-erythroascorbic acid starts from D-arabinose obtained by the microorganism from decaying plant material.
D-arabinose, presumably in its 1,4-furanosidic isomeric form, is oxidized by NAD(P)+ specific dehydrogenases to D-arabinono-1,4-lactone, which is further oxidized to D-erythroascorbic acid by D-arabinono-1,4-lactone oxidase.
Resting cells of Saccharomyces cerevisiae can synthesize Asc from L-galactose, L-galactono-1,4-lactone, or L-gulono- 1,4-lactone via the pathway naturally used for D-erythroascorbic acid.
Pharmaceutical Applications of Isoascorbic acid:
Isoascorbic acid is a stereoisomer of L-ascorbic acid, and is used as an antioxidant in foods and oral pharmaceutical formulations.
Isoascorbic acid has approximately 5% of the vitamin C activity of L-ascorbic acid.
Safety
Isoascorbic acid is widely used in food applications as an antioxidant.
Isoascorbic acid is also used in oral pharmaceutical applications as an antioxidant.
Isoascorbic acid is generally regarded as nontoxic and nonirritant when used as an excipient.
Isoascorbic acid is readily metabolized and does not affect the urinary excretion of ascorbic acid.
The WHO has set an acceptable daily intake of Isoascorbic acid and its sodium salt in foods at up to 5 mg/kg body-weight.
Isoascorbic acid (D-Isoascorbic acid), produced from sugars derived from different sources, such as beets, sugar cane, and corn, is a food additive used predominantly in meats, poultry, and soft drinks.
Isoascorbic acid is a stereoisomer of ascorbic acid.
Isoascorbic acid is widely used as a preservative and color stabilizer for foods and beverages.
As a vegetable-derived food additive, Isoascorbic acid can be considered natural.
Isoascorbic acid Uses:
Antioxidants, Bacon, Sauage, Meats, Brewing, Soft Drink, Beverage Powder, Fruit Juice, Ice Cream, Fruit Sauces, Chewing Gum, Confections, Baking Food, Yogurt, Color Stabilizer Flavoring Agent, Preservative, Nutrient, Dietary Supplement, Cosmetics, Feed, Pharmaceutical.
storage
Isoascorbic acid should be stored in an airtight container, protected from light, in a cool, dry place.
Purification Methods
Crystallise D(-)-isoascorbic acid from H2O, EtOH or dioxane. is at 245nm with 7,500 (EtOH).
Isoascorbic acid Used in various foods as water-soluble antioxidant to prevent change (color, taste, fragrance) of food occurred by oxidation.
Isoascorbic acid is found in frozen seafood, fishery product, stock meat, stock fish sausage, fruit, vegetable, pickles, beverage, gerry pet food etc.
Isoascorbic acid is also used as Oxygen absorbers (Sponge cake, Confectionery), boiler oxygen scavenger, photographic developer, hair dye and reaction-catalyst in resin polymerization.
Incompatibilities
Isoascorbic acid is incompatible with chemically active metals such as aluminum, copper, magnesium, and zinc.
Isoascorbic acid is also incompatible with strong bases and strong oxidizing agents.
Isoascorbic acid, a stereoisomer of ascorbic acid with similar physicochemical properties, is widely used as an antioxidant in processed foods.
Isoascorbic acid or erythorbate, formerly known as iso ascorbic acid and D-arabo ascorbic acid, is a stereoisomer of ascorbic acid.
Isoascorbic acids chemical properties have many similarities with Vc, but as an antioxidant, it has the inimitable advantage that Vc do not have:
First, Isoascorbic acid is superior to the anti-oxidation than Vc, therefore, mixed the Vc, it can effectively protect the properties Vc component in improving the properties have very good results, while protecting the Vc color.
Second, higher security, no residue in the human body, participating in metabolism after absorb by human body, which can be transformed into Vc partially.
Isoascorbic acid, an epimer of L-ascorbic acid, is used in the United States as a food additive.
Studies were conducted to determine whether the ingestion of Isoascorbic acid in the diet had any beneficial or adverse effects on the human requirement for vitamin C.
Young women were fed diets that contained controlled amounts of Isoascorbic acid and ascorbic acid.
In pharmacokinetic evaluations, Isoascorbic acid and ascorbic acid were rapidly absorbed with little interaction.
Isoascorbic acid cleared from the body more rapidly than ascorbic acid. Some subjects received diets deficient in vitamin C for periods < or = 30 d.
Increasing intakes of Isoascorbic acid or prolonged intakes of < or = 1 g Isoascorbic acid/d did not indicate any interactions with ascorbic acid.
Consumption of Isoascorbic acid resulted in the presence of Isoascorbic acid in mononuclear leukocytes.
Ascorbic acid concentrations in these cells were not affected by the presence of Isoascorbic acid.
Isoascorbic acid disappeared quickly from these cells with cessation of Isoascorbic acid supplements.
Prolonged ingestion of erythrobic acid by young women neither antagonized nor spared their vitamin C status.
How is Isoascorbic acid made?
Isoascorbic acid can be produced by a reaction between methyl 2-keto-D-gluconate and sulphuric acid.
Generally, the manufacturing process of Isoascorbic acid has 5 steps:
-Producing calcium 2-keto-D-gluconate: food-grade starch hydrolysate fermentation by Pseudomonas fluorescens with calcium carbonate.
-Acidify the above fermentation broth to obtain 2-keto-D-gluconic acid (2-KG).
-Esterification 2-KG with methanol under acid conditions to yield methyl 2-keto-D-gluconate.
-The synthesis of sodium erythorbate: heating the above suspension with sodium bicarbonate or sodium carbonate.
-The reaction between sodium erythorbate and sulphuric acid.
What’s The Application Of Isoascorbic acid?
Generally, Isoascorbic acid is widely used to stabilize color, reduce nitrate uses, and prevent oxidation in meat products, fruits and vegetables.
Meanwhile, Isoascorbic acid benefits our body through reducing nitrosamine formation which is generated by the intake of nitrate.
What Is Isoascorbic acid?
Ascorbyl Palmitate, Ascorbyl Dipalmitate and Ascorbyl Stearate are made from vitamin C (ascorbic acid).
Isoascorbic acid and Sodium Erythorbate are substances with structures similar to vitamin C and the sodium salt of vitamin C.
Ascorbyl Palmitate, Ascorbyl Dipalmitate and Ascorbyl Stearate are used primarily in makeup products.
Isoascorbic acid and Sodium Erythorbate are used primarily in hair and nail products.
Isoascorbic acid, formerly known as isoascorbic acid and D-araboascorbic acid, is a stereoisomer of ascorbic acid (vitamin C).
Isoascorbic acid is a vegetable-derived food additive produced from sucrose.
Isoascorbic acid is widely used as an antioxidant in processed foods.
The use of Isoascorbic acid as a food preservative has increased.
Isoascorbic acid is also used as a preservative in cured meats and frozen vegetables.
Why is Isoascorbic acid used in cosmetics and personal care products?
Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Isoascorbic acid and Sodium Erythorbate all function as antioxidants.
Isoascorbic acid
Isoascorbic acid also known as Isoascoribic acid, erythoribic acid is a natural product, vegetable derived food additive produced from sucrose.
Isoascorbic acid is an important antioxidant in the food industry, which can keep the color, natural flavor of foods and lengthen food storage without toxic and side effects.
Isoascorbic acid is used in cured meat processing, frozen fruits, frozen vegetables, jams, and in the beverage industry such as beer, grape wine, soft drink, fruit juice and fruit teas.
Isoascorbic acid’s use has increased tremendously ever since the U.S. Food and Drug Administration banned the use of sulfites as a preservative in foods to be eaten fresh (ie: salad bar ingredients).
Food
Isoascorbic acids main uses are in meat products, fruits & vegetables and also in soft drinks & beer.
Meat products
Cured and preserved meat products takes an important part in the meat industry.
Provide a bright red color
In order to achieve the purpose of preserving meat products and produce a bright red color, the traditional method is to add nitrate which can interact with amines in the human body to form a carcinogen nitrosamine, which is harmful to our health.
Reduce nitrosamines
Isoascorbic acid can significantly reduce the production of nitrosamines if the combination uses of Isoascorbic acid with nitrite.
At the same time, Isoascorbic acid can stabilize the color of meat.
Isoascorbic acid was reported by Mintel GNDP that nearly 5,000 products out of nearly 1 million products sold in Europe contain Isoascorbic acid or sodium erythorbate in meat products or products contained meat as an ingredient (e.g. pizza, ready-to-eat meat meals, meat-based spread and filled pasta).
Isoascorbic acid is a stereoisomer of ascorbic acid.
Isoascorbic acid is widely used as a preservative and color stabilizer for foods and beverages.
As a vegetable-derived food additive, Isoascorbic acid can be considered natural.
TYPES:
-Isoascorbic acid Powder
-Isoascorbic acid Granular
Fruits and Vegetable Processing
Fresh fruit and vegetable products can easily cause quality problems during the preservation, such as microbial growth, softening, weightlessness and browning due to cracks.
The traditional browning inhibitor is sulfur, but Isoascorbic acid can cause several health problems such as high blood pressure.
Isoascorbic acid or sodium erythorbate can be used to keep the freshness and stabilize the color of fruit and vegetables by soaking or spraying Isoascorbic acids solution on the surface.
Drink and Beer
Isoascorbic acid and Isoascorbic acids sodium salt can be used as an antioxidant in beverages, beer and etc.
Isoascorbic acid can eliminate the discoloration, odor and turbidity, and improve the poor taste of beverages.
In beer, Isoascorbic acid can remove the stale odor, enhance flavor stability, and prolong its shelf life.
Formerly known as isoascorbic acid, Isoascorbic acid is a stereoisomer of ascorbic acid (vitamin C).
Isoascorbic acid is a vegetable derived food additive produced from sucrose.
Isoascorbic acid is widely used as an antioxidant in processed foods.
Isoascorbic acid is a water-soluble antioxidant, used mainly as an ingredient in soft drinks.
Isoascorbic acid has no known mutagenic or carcinogenic properties, and has not been shown to inhibit the uptake of any vitamins or minerals.
Isoascorbic acid Uses: Antioxidant additive in food.
Cosmetics
Per the “European Commission database for information on cosmetic substances and ingredients”, Isoascorbic acid functions as an antioxidant in cosmetic and personal care products.
Isoascorbic acid can be found in hair and nail products.
Is Isoascorbic acid Safe to Eat?
Yes, Isoascorbic acids safety used as a food additive has been approved by the U.S. Food and Drug Administration (FDA), European Food Safety Authority (EFSA), Joint FAO/WHO Expert Committee on Food Additives (JECFA), as well as other authorities.
Isoascorbic acid is a stereoisomer of ascorbic acid (vitamin C) in the form on.
Isoascorbic acid is a widely used antioxidant.
Isoascorbic acid is mostly used as an antioxidant (industrial and food), especially in the brewing industry, and as a reducing agent for photography.
Isoascorbic acid a crystalline powder with a sugar like odor with dusts that have the tendency to cause mild irritation in eyes, skin, nose and throat.
Isoascorbic acid is used as a preservative in the food packaging.
The Isoascorbic acid market has been gaining significant traction from the food packaging industry owing to the ban over the use of sulfites as a preservative in canned and frozen foods resulting in rise in the market for Isoascorbic acid.
Isoascorbic acid is non-volatile and inflammable and is thus a popular product in the food preservation.
Apart from using a preservative Isoascorbic acid is also used as a color stabilizer in during food preservation.
Isoascorbic acid is also used in small quantities in pharmaceutical industry for preparation of various types of drugs.
Assay ≤ 99.0- 100.5%
Specific (a)D25 ≤ -16.5 – -18.0
Loss on drying ≤ 0.4 %
Heavy Metal ≤ 10 PPM
Lead ≤ 5 PPM
Arsenic ≤ 3 PPM
Residue on Ignition ≤ 0.3%
FDA
Isoascorbic acid is generally recognized as safe (GRAS) when used in accordance with good manufacturing practices in food and feed.
Isoascorbic acid can be used as an antimicrobial agent, antioxidant, color or coloring adjunct, curing or pickling agent, flavor enhancer, flavoring agent or adjuvant.
EFSA
Isoascorbic acid (E 315) is listed in Commission Regulation (EU) No 231/2012 as an authorised food additive in the EU as “Additives other than colours and sweeteners”.
Safety re-evaluation in 2016
After the studies of genotoxicity and carcinogenicity and others, EFSA claimed “there is no reason to revise the current ADI of 6 mg/kg bw/day and the use of Isoascorbic acid (E 315) and sodium erythorbate (E 316) as food additives at the permitted or reported use and use levels would not be of safety concern.”
Authorised Uses
The following foods may contain it:
-Cured and preserved meat products
-Frozen and deep-frozen fish with red skin
-Preserved and semi-preserved fish products
-Food Standards Australia New Zealand
-Isoascorbic acid is an approved ingredient in Australia and New Zealand with the code number 315.
Isoascorbic acid is readily absorbed and metabolized.
Following an oral dose of 500 mg of Isoascorbic acid to human subjects the blood level curves for ascorbic acid and Isoascorbic acid showed a similar rise.
In five human subjects, an oral dose of 300 mg was shown to have no effect on urinary excretion of ascorbic acid.
Isoascorbic acid was found to have no antagonistic effect on the action of ascorbic acid.
Isoascorbic acid (E315 or Isoascorbic Acid) is a white to slight yellow crystal or powder.
Isoascorbic acid can darken on exposure to light.
E315 is soluble in water, alcohol, pyridine, oxygenated solvents and slightly soluble in glycerin.
Possible Side Effects of Isoascorbic acid E315
Although Isoascorbic acid E315 generally regarded as a very safe and effective supplement, there can be some minor side effects.
The side effects may:
-Possible short-term side effects
-headaches
-dizziness
-fatigue
-body flushing
-hemolysis
JECFA
Food grade Specification, function class: Antioxidant.
What are the possible Side Effects of Isoascorbic acid?
Isoascorbic acid is common that sometimes consumers have questions whether Isoascorbic acid is bad for our health and what are the side effects in the food we eat.
However, Isoascorbic acid is generally considered safe and almost no reported health risks.
Maybe some people are allergic or sensitive to Isoascorbic acid.
Isoascorbic acid (syn: isoascorbic acid, D-araboascorbic acid) is a stereoisomer of ascorbic acid and has similar technological applications as a water-soluble antioxidant.
Isoascorbic acid was previously evaluated under the name isoascorbic acid by the sixth and seventeenth meetings of the Committee ; at the last evaluation an ADI of 0-5 mg/kg b.w. was allocated, based on a long-term study in rats, and a toxicological monograph was prepared.
The name Isoascorbic acid was changed to Isoascorbic acid in accordance with the “Guidelines for designating titles for specifications monographs” adopted at the thirty-third meeting of the Committee.
IUPAC name: D-erythro-Hex-2-enosono-1,4-lactone
Preferred IUPAC name: (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names: D-Araboascorbic acid, Erythorbate, Isoascorbic acid.
Antioxidants are molecules that can prevent other molecules from oxidation.
Isoascorbic acid is used as food additives in all kind of foodstuffs to lengthen their period of consumption.
For different meat foodstuffs, ascorbic acid (AA) and Isoascorbic acid (EA) are the most used antioxidants.
AA is not restricted as food additive and it can be added as much as its necessary, but the use of EA as food additive in meat matrixes cannot be higher than 500 mg/Kg (MRL).
Liquid chromatography (LC) is the chosen technique for the analysis of these compounds in complex matrixes.
The most conventional modalities of reversed phase do not give good resolution between AA and EA.
The main objective of this study is to establish a method based on liquid chromatography coupled with absorption spectrophotometry for the separation and quantification of AA and EA at concentrations near or below 500 mg/Kg.
The developed method is based on hydrophilic interaction liquid chromatography (HILIC), a modality of chromatography especially suitable for very polar compounds, which use is growing in the last years but is not as stablished as reversed phase modality.
Otherwise, the analytes tend to oxidise in aqueous solution.
Previous studies have been carried out: stability tests to avoid degradation of AA and EA and chromatographic conditions tests to achieve the optimal conditions for the separation and quantification of both analytes.
Extraction recovery, linearity, precision, trueness and uncertainty of the established method have been determined, and the results of the validation are fully satisfactory.
The method allows the confirmatory analysis of the analytes from 30 mg/Kg (LOQ) to concentrations higher than 500 mg/Kg (MRL)
Is Isoascorbic acidit Natural?
No, we can know Isoascorbic acid is synthetic from the manufacturing process mentioned above.
Is Isoascorbic acid Halal?
Yes, Isoascorbic acid is recognised as halal as it is permitted under the Islamic Law and fulfill the conditions of Halal and we can find some manufacturers certificated with MUI halal.
Origin:
Synthetic isomer of vitamin C, but with only 1/20 of the vitamin activity.
Function & characteristics:
Anti-oxidant.
Products:
Many products.
Acceptable Daily Intake:
No limit.
Side effects:
None known in the concentrations used.
Dietary restrictions:
Isoascorbic acid and erythorbates can normally be consumed by all religious groups, vegans and vegetarians
Isoascorbic acid assistant synthesis of CdS quantum dots (QDs) was conducted by homogeneous mixing of two continuous liquids in a high-throughput microporous tube-in-tube micro-channel reactor (MTMCR) at room temperature.
The effects of the micropore size of the MTMCR, liquid flow rate, mixing time and reactant concentration on the size and size distribution of CdS QDs were investigated.
Isoascorbic acid was found that the size and size distribution of CdS QDs could be tuned in the MTMCR.
A combination of Isoascorbic acid promoted formation technique with the MTMCR may be a promising pathway for controllable mass production of QDs.
Is Isoascorbic acid Kosher?
Yes, Isoascorbic acid is kosher pareve.
Isoascorbic acid has met all the “kashruth” requirements and can be certified as kosher or maybe kosher passover.
Is Isoascorbic acid Gluten free?
Yes, Isoascorbic acid is gluten free according to FDA that it does not contain wheat, rye, barley, or crossbreeds of these grains.
Is Isoascorbic acid Vegan?
Generally, Isoascorbic acid is vegan as the manufacturing process without the use of animal matter or products derived from animal origin.
So Isoascorbic acid is considered vegan and vegetarians can eat the food with it.
Melting point:169-172 °C (dec.) (lit.)
alpha -17.25 º (c=10, H2O 25 ºC)
Boiling point:227.71°C (rough estimate)
Density 1.3744 (rough estimate)
FEMA 2410 | ERYTHROBIC ACID
refractive index -17.5 ° (C=10, H2O)
storage temp. Store at 0-5°C
solubility H2O: 0.1 g/mL, clear, colorless to very faintly yellow
form Crystals or Crystalline Powder
pka4.09±0.10(Predicted)
color White to slightly yellow
optical activity[α]25/D 16.8°, c = 2 in H2O
Water Solubility 1g/10mL
Merck 14,5126
BRN 84271
Stability: Stable. Combustible.
Incompatible with chemically active metals, aluminium, zinc, copper, magnesium, strong bases, strong oxidizing agents.
InChIKey CIWBSHSKHKDKBQ-JLAZNSOCSA-N
Is Isoascorbic acid dairy free?
Yes.
Isoascorbic acid (C6H8O6) is a by product of ascorbic acid and is mainly used as a preservative of fruits and vegetables.
Uses of Isoascorbic acid:
-Bakes Goods
-Fats
-Oils
-Fruit Ices
-Gravies
What’s the Relationship between Isoascorbic acid and Ascorbic Acid?
Isoascorbic acid is a stereoisomer of ascorbic acid.
Isoascorbic acid vs Sodium Erythorbate?
The latter is more stable and is used widely in meat than the former.
The Food and Drug Administration (FDA) includes Ascorbyl Palmitate and Isoascorbic acid among the substances considered Generally Recognized As Safe (GRAS) as a chemical preservative.
Ascorbyl Palmitate is also specifically allowed to be used as a preservative in margarine.
The safety of Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Isoascorbic acid and Sodium Erythorbate has been assessed by the Cosmetic Ingredient Review (CIR) Expert Panel.
The CIR Expert Panel evaluated the scientific data and concluded that Ascorbyl Palmitate and the related ingredients were safe for use as cosmetic ingredients.
Conclusion
Isoascorbic acid (E315) and its sodium salt paly an important role in the meat industry.
Isoascorbic acid, a stereoisomer of ascorbic acid with similar physicochemical properties, is widely used as an antioxidant in processed foods.
The aims of the present study were to evaluate the effect of Isoascorbic acid on iron absorption from ferrous sulfate at molar ratios of 2:1 and 4:1 (relative to iron) and to compare the effect of Isoascorbic acid directly with that of ascorbic acid at a molar ratio of 4:1.
Iron absorption from iron-fortified cereal was measured in 10 women on the basis of erythrocyte incorporation of stable iron isotopes ((57)Fe or (58)Fe) 14 d after administration.
Each woman consumed 4 ferrous-sulfate-fortified test meals (containing 5 mg Fe/meal) with or without added erythorbic or ascorbic acid.
The data were evaluated by use of paired t tests, and the results are presented as geometric means.
Iron absorption from the test meal without any added enhancer was 4.1%.
The addition of Isoascorbic acid (at molar ratios of 2:1 and 4:1 relative to iron) increased iron absorption 2.6-fold (10.8%; P < 0.0001) and 4.6-fold (18.8%; P < 0.0001), respectively.
The addition of ascorbic acid (molar ratio of 4:1) increased iron absorption 2.9-fold (11.7%; P = 0.0004).
At a molar ratio of 4:1, Isoascorbic acid was 1.6-fold (P = 0.0002) as potent an enhancer of iron absorption as was ascorbic acid.
Although Isoascorbic acid is a potent enhancer of iron absorption, its lack of antiscorbutic activity limits its usefulness in iron-fortification programs.
However, Isoascorbic acid may play a major role in enhancing iron bioavailability from mixed diets that include foods preserved with Isoascorbic acid.
Appearance: White to slightly yellow crystalline solid which darkens gradually on exposure to light.
Other names: D-Isoascorbic acid; D-Araboascorbic acid
CAS number: 89-65-6
Chemical formula: C6H8O6
Molecular weight: 176.13
PKa: It is a diprotic acid having pKa’s 11.34 and 4.04.
Solubility
In water: 40 g in 100 mL water at 25 °C.
In organic solvents: Soluble in alcohol, pyridine; moderately soluble in acetone; slightly soluble in glycerol
Isoascorbic acid is a stereoisomer of ascorbic acid (Vitamin C).
While ascorbic acid is allowed as a synthetic ingredient in or on processed organic products at §205.605 in the NOP regulations, the issue of stereoisomers is not addressed in the rule.
A stereoisomer is a molecule that has the same formula and sequence of bonded atoms as another, but differs in its three-dimensional orientation.
For example, if your hands were molecules and your palm and digits atoms, your left hand would be a stereoisomer of your right.
Both ascorbic acid and Isoascorbic acid are commonly used as anti-oxidant preservatives in a wide variety of foods.
The use of Isoascorbic acid as a preservative in foods intended to be eaten raw has increased since the US FDA banned the use of sulfites for this purpose.
Since the NOSB did not specifically discuss Isoascorbic acid during its Technical Advisory Panel (TAP) reviews for Ascorbic acid, the real question is whether or not Isoascorbic acid is chemically the same as ascorbic acid.
The materials have different CAS registry numbers, and this is an indication that they are distinct chemicals.
One does not fall under the identity of the other, according to the American Chemical Society.
While studies show that natural and synthetic ascorbic acid behave similarly in biologic systems, stereoisomers of ascorbic acid show a decreased anti-ascorbutic activity in comparison.
This is a clear indication that the materials are functionally different in metabolic systems, at least in degree.
OMRI consequently regards the two materials as chemically and functionally distinct, and does not consider Isoascorbic acid to be included in the allowance of ascorbic acid for organic processing.
Those wishing to use the ingredient in organic processing would be encouraged to petition the NOP to have Isoascorbic acid specifically addressed.
CAS Number: 89-65-6
CHEBI: 51438
ChemSpider: 16736142
ECHA InfoCard: 100.001.753
E number: E315 (antioxidants, …)
PubChem CID: 6981
UNII: 311332OII1
CompTox Dashboard (EPA): DTXSID6026537
Chemical formula: C6H8O6
Molar mass: 176.124 g·mol−1
Density 0.704 g/cm3
Melting point: 164 to 172 °C (327 to 342 °F; 437 to 445 K)
Isoascorbic acid and Ascorbic Acid as Antioxidants in Bottled wines
The relatively high sulfur dioxide content of bottled wines is detrimental to aroma and flavor.
This can be avoided by intelligent use of erythorbic or ascorbic acid.
The addition of ½ to 1.4 pound of Isoascorbic acid per 1,000 gallons of wine appeared to be the optimum level for the improvement of aroma and flavor in bottled wines when observed during 30 month’s storage.
The wines in this study unfortunately had a relatively high sulfur dioxide content, and the addition of erythorbic or ascorbic acid at 1.6 lb/1,000 gal or more aggravated this detrimental effect.
In general, a relatively high sulfur dioxide content appears detrimental to the improvement of aroma and flavor of bottled wines, and particularly of white wine.
Our observations suggest that a lower initial sulfur dioxide content in these wines would have showed a greater improvement in aroma and flavor at the addition level of ½ to 1.4 lb/1,000 gal of Isoascorbic acid, when held under the same conditions.
Further tests should be made by the industry at large to establish the optimum sulfur dioxide concentration and the optimum addition level of Isoascorbic acid for wines in general, both in bulk storage and in bottles.
EYE CONTACT FIRST AID:
After initial flushing, remove any contact lenses and continue flushing for at least 15 minutes.
Get medical attention if irritation develops or persists.
SKIN CONTACT FIRST AID:
Wash affected area immediately with large amounts of soap and water.
Get medical attention if irritation develops or persists.
INHALATION FIRST AID:
Remove to fresh air, treat symptomatically.
Get medical attention if cough or other symptoms develop.
INGESTION FIRST AID:
If swallowed, do NOT induce vomiting. Give milk or water.
Never give anything by mouth to an unconscious person.
Call a physician or poison control center immediately
Isoascorbic acid
Isoascorbic acid
D-Isoascorbic acid
89-65-6
D-Araboascorbic acid
Araboascorbic acid
D-Isoascorbic acid
Isovitamin C
2,3-Didehydro-D-erythro-hexono-1,4-lactone
Erycorbin
Neo-cebicure
UNII-311332OII1
Saccharosonic acid
Glucosaccharonic acid
MFCD00005378
(5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
D-erythro-Hex-2-enonic acid, g-lactone
D-erythro-hex-2-enonic acid gamma-lactone
D-(-)-Isoascorbic acid
CHEBI:51438
(R)-5-((R)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
D-ASCORBIC ACID, ISO
D-erythro-hex-2-enono-1,4-lactone
311332OII1
Mercate 5
D(-)-Isoascorbic acid, 98%
D-erythro-Hex-2-enonic acid, .gamma.-lactone
Erythroascorbic acid, D-
FEMA Number: 2410
FEMA No. 2410
CCRIS 6568
The performance of Isoascorbic acid has been evaluated within thermally aged MEG.
Strong to acceptable oxygen removal performance was demonstrated at pH of 11 and 9.
The Isoascorbic acid demonstrated poor oxygen removal performance at a pH of 6.
Little to no impact observed due to the presence of mineral ions or acetic acid.
Isoascorbic acid is used extensively as an antioxidant in foods.
Isoascorbic acid has one-twentieth the vitamin C activity of ascorbic acid, and is sometimes also referred to as isovitamin C.
Isoascorbic acid is soluble in water, and is provided as fine, shiny crystals.
Isoascorbic acid is produced to meet the specifications of The Food Chemical Codex.
The material is also used in the production of specialty latex resins.
Isoascorbic acid, FCC is used as a food preservative additive.
The FCC grade meets the requirements of the Food Chemical Codex indicates and is suitable for all food, beverage and nutritional supplement applications.
Spectrum Chemical offers over 300 Food grade chemical ingredients packaged in laboratory size bottles to production drum quantities and are manufactured, packaged and stored under current Good Manufacturing Practices (cGMP) per 21CFR part 211 in FDA registered and inspected facilities.
SAFEGUARDS (PERSONNEL):
If excessive dust is created, wear dust mask or respirator to keep exposure below the Permissible Exposure Level for particulate matter.
Wear appropriate personal protective equipment.
INITIAL CONTAINMENT:
Take up and place in secure closed containers.
Treat or dispose of waste material in accordance with all local, state/provincial, and national requirements.
Pick up and arrange disposal without creating dust.
LARGE SPILLS PROCEDURE:
Avoid dust generation.
Treat or dispose of waste material in accordance with all local, state/provincial, and national requirements.
SMALL SPILLS PROCEDURE:
Do not dry sweep.
Treat or dispose of waste material in accordance with all local, state/provincial, and national requirements.
HANDLING (PERSONNEL):
Wash hands thoroughly after handling.
Avoid contact with eyes, skin, and clothing.
Avoid breathing (dust, vapor, mist, gas).
HANDLING (PHYSICAL ASPECTS):
Store in original container protected from direct sunlight in a dry, cool and well-ventilated area, away from incompatible materials.
Secure container after each use.
STORAGE PRECAUTIONS:
Keep dry
ENGINEERING CONTROLS:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Good general ventilation should be sufficient to control airborne levels.
Ensure adequate ventilation, especially in confined areas.
EYE / FACE PROTECTION REQUIREMENTS:
A respiratory protection program that meets OSHA’s 29 CFR 1910-134 and ANSI Z88-2 requirements must be followed whenever workplace conditions warrant a respirator’s use.
SKIN PROTECTION REQUIREMENTS:
Apron is recommended. Wear protective gloves to minimize skin contamination.
Wash hands thoroughly after handling.
RESPIRATORY PROTECTION REQUIREMENTS:
If airborne concentrations exceed the OSHA TWA, a NIOSH approved dust mask is recommended.
APPEARANCE
White to yellow crystalline or granular solid
FUNCTION
Is a food preservative that is a strong reducing agent (oxygen accepting) which functions similarly to antioxidants.
Isoascorbic acid is used in meat curing to speed and control the nitrite curing reaction and prolong the color of cured meat at levels of 0.05%.
SYNONYMS
Isoascorbic acid FCC K PDR; Isoascorbic acid FCC; Uantox EBATE; 2,3-didehydro-d-erythro-hexono-1,4-lactone; Erycorbin; Saccharosonic Acid; D(-)-Isoascorbic Acid
STORAGE
Keep container tightly closed when not in use. Store containers in a cool, dry location, away from direct sunlight, sources of intense heat, or where freezing is possible.
FORM: Solid
COLOR: White
ODOR: None
BOILING POINT: ND C
VAPOR PRESSURE: ND psia
VAPOR DENSITY: ND (Air = 1)
SOLUBILITY IN WATER: 40 g/100 ml
SPECIFIC GRAVITY: 1.65 (Water = 1)
BULK DENSITY: ND
MELTING/FREEZING POINT: ND C
PH: 5-6
% VOLATILES: ND %
CAS number: 89-65-6
EINECS, EC No.: 201-928-0
HS Code: 2932290090
Synonyms: (5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one; D-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315, Isovitamin C; D-araboascorbic acid; D-erythro-Hex-2-enonic acid, gamma-lactone; D-Isoascorbic Acid.
Molecular formula: C6H8O6
Molecular weight: 176.13 g/mol
Isoascorbic acid is a stereoisomer of ascorbic acid widely used as antioxidant in food processing.
As a antioxidant, Isoascorbic acid can be used in a wide variety of industries including: food production, beverage, pharmaceutical, and various other industries.
Isoascorbic acid in Food Production
Isoascorbic acid is widely used as Color fixative, Preservatives, Acidity Regulators, nutrition supplements in food production.
Isoascorbic acid As Color fixative, Preservatives: in food industries to prevent colored food from discoloration.
Isoascorbic acid As Acidity Regulators: in food industries to improve sour.
Isoascorbic acid As nutritional supplement: in food industries to add vitamin.
Identification: Passes Test
Appearance: White odorless crystalline powder.
Assay: 99.0 – 100.5%
Specific Rotation, [a ]25°/D °C: Between -16.5° and -18.0°
Heavy Metals: 10 ppm max
Lead: 5 ppm max
ArseniC: 3 ppm max
Residue on Ignition,: >0.3% max
Loss on Drying: 0.4% max
Packing: 25-kg (55-lb) or as required by the buyer
Isoascorbic acid in Beverage
Isoascorbic acid is widely used as Preservatives, Acidity Regulators, nutrition supplements in beverage.
Isoascorbic acid As Preservatives: in beverage industries to prevent colored food from discoloration.
Isoascorbic acid As Acidity Regulators: in beverage industries to improve sour.
Isoascorbic acid As nutritional supplement: in beverage industries to add vitamin.
Isoascorbic acid in Pharmaceutical
Isoascorbic acid is widely used as antioxidants in Pharmaceutical.
Isoascorbic acid As antioxidants: in treatment of Scurvy and chronic iron poisoning.
Isoascorbic acid in Cosmetics Not enough is known about application of Isoascorbic acid in Cosmetics.
Isoascorbic acid in Agriculture/Animal Feed Not enough is known about application of Isoascorbic acid in Agriculture/Animal Feed.
Isoascorbic acid in Other Industries Not enough is known about application of Isoascorbic acid in other industries.
STABILITY:
Stable.
POLYMERIZATION:
Hazardous polymerization will not occur.
INCOMPATIBILITY WITH OTHER MATERIALS:
Strong oxidizing agents.
Strong Bases.
Chemically active metals, Aluminum, Zinc, Magnesium, Copper.
DECOMPOSITION:
Carbon Oxides.
Isoascorbic acid is used in our products mainly as antioxidant.
Antioxidants scavenge oxygen molecules or interrupt the formation of free radicals (which happens when oxygen molecules react with other species).
Isoascorbic acid Without antioxidants cosmetic products might spoil (turn rancid), change colors, or otherwise degrade in quality or shelf life
HSDB 584
Isoascorbic acid [NF]
D-erythro-Hex-2-enonic acid, gamma-lactone
NSC 8117
D-erythro-3-Oxohexonic acid lactone
EINECS 201-928-0
D-erythro-3-Ketohexonic acid lactone
3-Oxohexonic acid lactone, D-erythro-
BRN 0084271
3-Keto-D-erythro-hexonic acid gamma-lactone
Hex-2-enonic acid gamma-lactone, D-erythro-
d-iso-ascorbic acid
1f9g
E315
D-Erythro-hex-2-enonic acid, gamma-lactone,
DSSTox_CID_6537
D-(-)-Araboascorbic acid
EC 201-928-0
DSSTox_RID_78143
D-(???)-Isoascorbic acid
DSSTox_GSID_26537
SCHEMBL18678
5-18-05-00026 (Beilstein Handbook Reference)
CHEMBL486293
SCHEMBL3700961
DTXSID6026537
D-(-)-Isoascorbic acid, 98%
(2R)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyfuran-3-one
HY-N7079
Tox21_201111
SBB017515
AKOS015856346
ZINC100006772
ZINC100057602
CAS-89-65-6
D-erythro-hex-2-enoic acid ??-lactone
NCGC00258663-01
D-Isoascorbic acid, >=99%, FCC, FG
O272
A0520
CS-0014152
C20364
Q424531
J-506944
7179C406-7CCF-4C07-9125-AA71E28FB983
(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
(5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-hydrofuran-2-one
Isoascorbic acid, United States Pharmacopeia (USP) Reference Standard
(5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (non-preferred name)
Isoascorbic Acid
D-araboascorbic Acid
Araboascorbic Acid
D-Isoascorbic acid
Isovitamin C
D-isoascorbic Acid
Erycorbin
Neo-cebicure
Saccharosonic Acid
Mercate 5
Isoascorbic acid, an epimer of L-ascorbic acid, is used in the United States as a food additive.
Isoascorbic acid was studied, that Isoascorbic acid enhanced of iron absorption and could play a major role in enhancing iron bioavailability from mixed diets that include foods preserved with Isoascorbic acid.
In addition, was investigated if the Isoascorbic acid could influence on the metabolism of vitamin C in young women, and obtained results showed, that prolonged ingestion of Isoascorbic acid had no effect on vitamin C uptake or clearance from the body.
Isoascorbic acid The d‐isomer of ascorbic acid, also called D‐araboascorbic acid and iso‐ascorbic acid, with only slight vitamin C activity.
Isoascorbic acid is used in foods as an antioxidant.
Ascorbic acid and erythorbate have been widely used in recent years to improve the color of cured meats.
Watts and Lehman (1952a) found that 0.1 percent ascorbic acid added to meats caused better color development when the meat was heated at 70°C. or frozen at -17°C.
These workers (1952b) observed that hemoglobin did not react with ascorbic acid in the absence of oxygen.
Ascorbic acid reduced methemoglobin and promoted the reduction of nitrite to nitric oxide.
In the presence of oxygen, an undesirable side reaction occurred in which the green pigment choleglobin was formed.
According to Hollerbeck and Monahan (1953), the beneficial effect of ascorbic acid in curing meat is due to the reduction of nitrogen dioxide to nitric oxide.
Kelley and Watts (1957) observed that cysteine, ascorbic acid, and glutathione were capable of promoting the formation of nitric oxide hemoglobin, regenerating this pigment on surfaces of faded meat and protecting surfaces of cured meat from fading when exposed to light.”
Glucosaccharonic Acid
D-(-)-isoascorbic Acid
Erythroascorbic Acid, D-
Fema Number: 2410
D-ascorbic Acid, Iso
Fema No. 2410
Ccris 6568
Hsdb 584
D-erythro-hex-2-enonic Acid, Gamma-lactone
2,3-didehydro-d-erythro-hexono-1,4-lactone
Unii-311332oii1
Chebi:51438
89-65-6
Nsc 8117
D-erythro-3-oxohexonic Acid Lactone
Einecs 201-928-0
D-erythro-3-ketohexonic Acid Lactone
3-oxohexonic Acid Lactone, D-erythro-
Brn 0084271
E315
Hazard statement: causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Response: if on skin: wash with plenty of water.
If skin irritation occurs: get medical advice/attention.
Takeoff contaminated clothing and wash before reuse.
If in eyes: rinse cautiously with water forseveral minutes.
Remove contact lenses, if present and easy to do.
Continue rinsing.
If eyeirritation persists: get medical advice/attention.
If inhaled: remove person to fresh air and keepcomfortable for breathing.
Call a poison center/doctor if you feel unwell.
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one
3-keto-d-erythro-hexonic Acid Gamma-lactone
D-erythro-hex-2-enonic Acid, Gamma-lactone,
Hex-2-enonic Acid Gamma-lactone, D-erythro-
Erythroascorbic Acid
D-erythro-hex-2-enoic Acid Gamma-lactone
D-erythro-hex-2-enonic Acid, .gamma.-lactone
Erythorbatd
D-erythro-hex-1-enofuranos-3-ulose
Isoascorbic acid [nf]
1f9g
Ac1l1nqg
Dsstox_cid_6537
Dsstox_rid_78143
Dsstox_gsid_26537
Schembl18678
W241008_aldrich
856061_aldrich
Chembl486293
Schembl3700961
58320_fluka
Ciwbshskhkdkbq-duzgatohsa-n
Molport-003-937-345
7378-23-6 (hydrochloride Salt)
Tox21_201111
Ar-1i3651
D-erythro-hex-2-enono-1,4-lactone
Sbb017515
146-75-8 (di-hydrochloride Salt)
Akos015856346
311332oii1
Ls-2352
Rl05634
Cas-89-65-6
6381-77-7 (mono-hydrochloride Salt)
Ncgc00258663-01
Kb-49577
O272
D-erythro-hex-2-enonic Acid Gamma-lactone
A0520
C20364
5-18-05-00026 (beilstein Handbook Reference)
(2r)-2-[(1r)-1,2-dihydroxyethyl]-4,5-dihydroxyfuran-3-one
7179c406-7ccf-4c07-9125-aa71e28fb983
(5r)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-hydrofuran-2-one
74242-57-2