Erythorbic acid E315 is a white to slightly yellow crystalline powder or granule with a mildly sour taste, derived from natural sources like sugar beets or synthesized through fermentation.

Erythorbic acid E315 can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature.

Erythorbic acid E315 is frequently used as a cost-effective alternative to ascorbic acid, offering similar antioxidant benefits.

CAS Number: 89-65-6

EC Number: 201-929-0

Molecular Formula: C6H8O6

Molecular Weight: 176.12 g/mol

Synonyms: D-erythro-ascorbic acid, D-(-)-Isoascorbic acid, (R)-5-((R)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one, MFCD00005378, D-erythro-Hex-2-enonic acid, g-lactone, D-erythro-hex-2-enonic acid gamma-lactone, Erythorbic acid E315 (Standard), SCHEMBL18678, Erythorbic acid E315 [II], 5-18-05-00026 (Beilstein Handbook Reference), Erythorbic acid E315 [FCC], ISOASCORBIC ACID [MI], Erythorbic acid E315 [FHFI], Erythorbic acid E315 [HSDB], CHEMBL486293, SCHEMBL3700961, Sodium Ascorbate EP Impurity F, Erythorbic acid E315 [MART.], HY-N7079R, Erythorbic acid E315 [USP-RS], MSK2311, D-(-)-Isoascorbic acid, 98%, HY-N7079, Tox21_201111, AC8021, SBB017515, AKOS015856346, D-erythro-hex-2-enoic acid ?-lactone, EBC-146034, FI09585, CAS-89-65-6, NCGC00258663-01, D-ASCORBIC ACID, ISO, D-erythro-hex-2-enono-1,4-lactone, D(-)-Isoascorbic Acid (Erythorbic acid E315), Erythroascorbic acid, D-, (5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one, Araboascorbic acid, D-, CCRIS 6568, HSDB 584, D(-?)?-?Isoascorbic Acid (Erythorbic acid E315), Erythorbic acid E315 [NF], NSC 8117, EINECS 201-928-0, 3-Oxohexonic acid lactone, D-erythro-, BRN 0084271, Ascorbic Acid EP Impurity F, Hex-2-enonic acid gamma-lactone, D-erythro-, UNII-311332OII1, D-soascorbic acid, (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (D-Isoascorbic Acid), (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (D-Isoascorbic Acid); Ascorbic Acid Impurity F; Sodium Ascorbate Impurity F, d-iso-ascorbic acid, ISOASCORBIC-ACID, d(-)-isoascorbic acid, 1f9g, E315, D-arabino-Ascorbic acid, D-Erythro-hex-2-enonic acid, gamma-lactone,, EC 201-928-0

Erythorbic acid E315 is a synthetic stereoisomer of ascorbic acid widely used in the food industry as a potent antioxidant.

Erythorbic acid E315 functions primarily as a reducing agent, helping to prevent oxidation, preserve color, and maintain the quality of food products, especially in processed meats.

Although structurally similar to vitamin C, Erythorbic acid E315 has very low biological activity as a vitamin.

Erythorbic acid E315 is highly effective in inhibiting lipid oxidation and enzymatic browning, thereby extending shelf life and improving the stability of food formulations.

Erythorbic acid E315 is a crucial antioxidant used widely in the food industry to preserve color, flavor, and freshness.

Erythorbic acid E315 is a stereoisomer of ascorbic acid (Vitamin C), but it lacks the vitamin’s nutritional properties.

Erythorbic acid E315 is highly effective at preventing oxidative browning in fruits, vegetables, and beverages.

Due to its powerful preservative qualities, Erythorbic acid E315 significantly extends the shelf life of many food products.

This makes Erythorbic acid E315 an invaluable ingredient for food manufacturers seeking to maintain product quality and appeal over time.

The use of erythrobic acid is a common and accepted practice in food processing worldwide.

Erythorbic acid E315 is a white to slightly yellow crystalline powder or granule with a mildly sour taste, derived from natural sources like sugar beets or synthesized through fermentation.

Erythorbic acid E315 functions as a potent antioxidant, effectively scavenging free radicals and preventing oxidative damage in food, pharmaceutical, and cosmetic products.

Erythorbic acid E315 is non-toxic and generally recognized as safe (GRAS) by regulatory authorities worldwide.

Erythorbic acid E315 is highly soluble in water and slightly soluble in alcohol, making it versatile for a wide range of applications.

Erythorbic acid E315's stability under heat and light ensures reliable performance in both manufacturing and end-product conditions.

Erythorbic acid E315 is frequently used as a cost-effective alternative to ascorbic acid, offering similar antioxidant benefits.

Erythorbic acid E315 is a stereoisomer (C5 epimer) of ascorbic acid (vitamin C).

Erythorbic acid E315 is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide.

Erythorbic acid E315 can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature.

Erythorbic acid E315 is widely used as an antioxidant in processed foods.

Related Compounds of Erythorbic Acid E315:

The structurally similar C5 sugar acid, D-erythroascorbic acid, is made by baker's yeast and other fungi, acting as an antioxidant in their own cells.

Erythorbic acid E315 is made by and has some antioxidant activity in Manduca sexta.

Erythorbic acid E315 has no industrial use, however.

Economics of Erythorbic Acid E315:

Like ascorbic acid, the production of Erythorbic acid E315 is concentrated in China.

Erythorbic acid E315's price is less volatile than that of ascorbic acid, making it an attractive alternative in non-nutritive uses in times of high ascorbic acid prices.

Uses of Erythorbic Acid E315:

Erythorbic acid E315 is primarily used as an antioxidant in the food industry to prevent oxidation and maintain product quality.

Erythorbic acid E315 is widely applied in processed meat products such as sausages, cured meats, and canned meats to stabilize color by keeping myoglobin in its reduced form and to enhance the effectiveness of nitrites during curing.

Erythorbic acid E315 is also used in beverages, fruit and vegetable products, and canned foods to prevent enzymatic browning and preserve freshness.

Additionally, Erythorbic acid E315 is utilized in some food formulations to protect flavor, delay rancidity, and extend shelf life without contributing significant vitamin activity.

Erythorbic acid E315 is widely used in the food industry as an antioxidant to prevent oxidation of fats, oils, and beverages.

Erythorbic acid E315 is employed in cured meats, such as sausages and hams, to maintain their color and enhance preservation.

Erythorbic acid E315 is included in canned fruits and vegetables to retain their natural color and freshness.

Erythorbic acid E315 is used in the pharmaceutical industry as an excipient and stabilizer in vitamin C formulations.

Erythorbic acid E315 is incorporated into cosmetics and personal care products as an antioxidant to enhance stability and prevent product degradation.

Erythorbic acid E315 is included in industrial applications, such as in the production of resins and plastics, to prevent oxidative damage during processing.

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 Erythorbic acid E315 as a food preservative has increased.

Erythorbic acid E315 is also used as a preservative in cured meats and frozen vegetables.

Much like ascorbic acid, Erythorbic acid E315 increases nitrosylation of the central iron atom of muscle myoglobin, resulting in the formation of reddish-brown nitrosomyoglobin and the characteristic pink color of nitrosohemochrome or nitrosyl-heme upon cooking.

Again like ascorbic acid, Erythorbic acid E315 reduces the formation of nitrosamines.

Meat products:

Erythorbic acid E315 is used in sausages, cured meats, and canned meats to stabilize color, prevent oxidation, and enhance nitrite curing efficiency.

Beverages:

Erythorbic acid E315 is added to beverages to prevent oxidation and maintain flavor stability.

Fruits and vegetables:

Erythorbic acid E315 is used to inhibit enzymatic browning and preserve freshness in fresh-cut or processed products.

Canned foods:

Erythorbic acid E315 is used in canned foods to maintain color, flavor, and overall product quality during storage.

Antioxidant systems:

Erythorbic acid E315 functions as a reducing agent to delay lipid oxidation and extend shelf life in various food formulations.

Industry Uses:

Corrosion inhibitors and anti-scaling agents

Not Known or Reasonably Ascertainable

Pigment

Other (specify)

Reducing agent

Paint additives and coating additives not described by other categories

Surface active agents

Process regulators

Binder

Consumer Uses:

Corrosion inhibitors and anti-scaling agents

Not Known or Reasonably Ascertainable

Reducing agent

Other (specify)

Surface active agents

Paint additives and coating additives not described by other categories

Catalyst

Binder

Process regulators

Applications Across Industries:

Erythorbic acid E315’s versatility makes it a valuable additive in various food sectors.

In the meat industry, Erythorbic acid E315 is used in cured meats like sausages and bacon.

Erythorbic acid E315 helps to preserve the color and prevents rancidity.

In the beverage industry, Erythorbic acid E315 is used in juices, soft drinks, and beer.

Here, Erythorbic acid E315 prevents oxidation and maintains flavor stability.

For fruit and vegetable processors, Erythorbic acid E315 is a key ingredient in canned and frozen products.

Erythorbic acid E315 maintains their color and texture.

Erythorbic acid E315's use extends to baked goods as well, where it can act as a dough improver.

This wide range of applications underscores its importance.

Erythorbic acid E315 is a foundational ingredient for many food manufacturing processes.

Benefits of Erythorbic Acid E315:

The use of Erythorbic acid E315 provides numerous benefits for food producers.

Firstly, Erythorbic acid E315 effectively prevents the browning of fruits and vegetables.

This preserves their natural color and visual appeal.

For producers of pre-cut salads, fruit salads, and canned fruits, this is a major advantage.

Secondly, Erythorbic acid E315 plays a vital role in the meat processing industry.

Erythorbic acid E315 helps maintain the vibrant red color of fresh meats and processed meat products.

Erythorbic acid E315 also prevents the formation of nitrosamines, which are harmful compounds.

This dual function makes Erythorbic acid E315 an indispensable component in many meat formulations.

Furthermore, Erythorbic acid E315 enhances the effectiveness of other preservatives, such as nitrates and nitrites.

Erythorbic acid E315 allows for their use at lower levels, which is beneficial for public health.

Health effects:

Clinical trials have been conducted to investigate aspects of the nutritional value of Erythorbic acid E315.

One such trial investigated the effects of Erythorbic acid E315 on vitamin C metabolism in young women; no effect on vitamin C uptake or clearance from the body was found.

A later study found that Erythorbic acid E315 is a potent enhancer of nonheme-iron absorption, just like ascorbate.

This is thought to be due to it exerting the same iron-reducing and iron-chelating activity as ascorbic acid.

Neither of these reactions is mediated by an enzyme, which would confer some chiral selectivity.

Erythorbic acid E315 is twice as effective as ascorbic acid in enhancing non-heme iron absorption.

Americans are estimated to ingest 200 mg of Erythorbic acid E315 per day, making it a very important factor in understanding iron absorption.

Productions of Erythorbic Acid E315:

Erythorbic acid E315 is very easily produced by fermentation, being obtainable in just one step compared to ascorbic acid's two.

A number of Penicillium naturally produce this chemical from glucose.

This is the original process developed in the 1960s, but Erythorbic acid E315 has low volumetric efficiency and glucose yield compared to the modern method.

Today the industrial process is quite similar to the Reichstein process used for ascorbic acid, only chirally flipped.

Microbial fermentation first produces a 2-keto-sugar acid, e.g. by Pseudomonas fluorescens AR4 converting glucose to 2-keto-D-gluconate.

Then chemical rearrangement produces the product.

History of Erythorbic Acid E315:

Erythorbic acid E315 was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.

Stability and Reactivity of Erythorbic Acid E315:

Chemical stability:

Erythorbic acid E315 is unstable in the presence of air.

Erythorbic acid E315 is sensitive to light and heat.

Reactivity:

Erythorbic acid E315 acts as a strong reducing agent.

Erythorbic acid E315 reacts readily with oxygen.

Erythorbic acid E315 reacts with oxidizing agents.

Conditions to avoid:

Light exposure.

Oxygen exposure.

High temperatures.

Alkaline conditions.

Incompatible materials:

Strong oxidizing agents.

Alkalis.

Hazardous decomposition products:

Thermal decomposition may produce carbon oxides (CO, CO₂).

Handling and Storage of Erythorbic Acid E315:

Handling:

Handle in a way that minimizes exposure to air and moisture.

Avoid dust formation.

Use appropriate protective equipment.

Storage:

Store in tightly closed containers in a cool, dry, and dark place.

Protect from light and oxygen.

First Aid Measures of Erythorbic Acid E315:

Inhalation:

Move the affected person to fresh air.

Seek medical attention if symptoms persist.

Skin contact:

Wash the affected area thoroughly with water.

Remove contaminated clothing.

Eye contact:

Rinse cautiously with water for several minutes.

Seek medical advice if irritation continues.

Ingestion:

Rinse mouth with water.

Seek medical advice if discomfort occurs.

Firefighting Measures of Erythorbic Acid E315:

Suitable extinguishing media:

Water spray.

Foam.

Carbon dioxide (CO₂).

Dry chemical powder.

Specific hazards:

Combustion may produce carbon oxides.

Irritating fumes may be generated.

Protective equipment:

Firefighters should wear self-contained breathing apparatus (SCBA).

Wear protective clothing.

Accidental Release Measures of Erythorbic Acid E315:

Personal precautions:

Ensure adequate ventilation.

Avoid contact with skin and eyes.

Prevent dust inhalation.

Environmental precautions:

Prevent large quantities from entering drains, soil, or water systems.

Methods for cleaning up:

Carefully sweep or collect to avoid dust formation.

Place in suitable containers for disposal.

Exposure Controls / Personal Protection of Erythorbic Acid E315:

Engineering controls:

Provide adequate ventilation to control dust levels.

Eye/face protection:

Use safety goggles.

Skin protection:

Wear protective gloves.

Wear suitable work clothing.

Respiratory protection:

Use a dust mask or appropriate respiratory protection if airborne particles are present.

Hygiene measures:

Wash hands thoroughly after handling.

Avoid eating, drinking, or smoking during use.

Identifiers of Erythorbic Acid E315:

CAS Number: 89-65-6.

EC Number: 201-929-0.

Food Additive Code: E315.

IUPAC Name: (2R,3S)-3,4-dihydroxy-2,5-dioxo-2,5-dihydrofuran-3-yl acetate.

Molecular Formula: C6H8O6.

Molecular Weight: 176.12 g/mol.

PubChem CID: 54670067.

CAS Number: 89-65-6

ChEBI: CHEBI:51438

ChemSpider: 16736142

ECHA InfoCard: 100.001.753

E number: E315 (antioxidants, ...)

PubChem CID: 6981

UNII: 311332OII1

CompTox Dashboard (EPA): DTXSID6026537

InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1

Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N

InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1

Key: CIWBSHSKHKDKBQ-DUZGATOHBV

SMILES: OC=1[C@H](OC(=O)C=1O)[C@H](O)CO

Properties of Erythorbic Acid E315:

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) (decomposes)

Acidity (pKa): 2.1

Appearance: White to slightly yellow crystalline powder.

Odor: Odorless.

Taste: Slightly acidic.

pH: ~2.5–3.5.

Melting Point: ~160–165°C (decomposes).

Solubility: Highly soluble in water.

Stability: Sensitive to light, heat, and oxygen.

Chemical Formula: C6H8O6

Molecular Weight: 176.12 g/mol

Common Name: Erythorbic acid E315

Appearance: White to slightly yellow crystalline powder or granules

Density: Approx. 1.65 g/cm³

Melting Point: Approx. 164–168°C

Boiling Point: Decomposes before boiling

Solubility: Highly soluble in water; slightly soluble in ethanol

pH (10% Solution): Slightly acidic (approx. 2.5–3.5)

Chemical Stability: Stable in recommended storage conditions

Vapor Pressure: Negligible

Molecular Weight: 176.12 g/mol

XLogP3: -1.6

Hydrogen Bond Donor Count: 4

Hydrogen Bond Acceptor Count: 6

Rotatable Bond Count: 2

Exact Mass: 176.03208797 Da

Monoisotopic Mass: 176.03208797 Da

Topological Polar Surface Area: 107 Ų

Heavy Atom Count: 12

Complexity: 232

Isotope Atom Count: 0

Defined Atom Stereocenter Count: 2

Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0

Undefined Bond Stereocenter Count: 0

Covalently-Bonded Unit Count: 1

Compound Is Canonicalized: Yes

Related compounds of Erythorbic Acid E315:

Other cations:

Calcium erythorbate

sodium erythorbate

potassium erythorbate

Names of Erythorbic Acid E315:

IUPAC name:

D-erythro-Hex-2-enono-1,4-lactone

Systematic IUPAC name:

(5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one

Other names:

D-Araboascorbic acid

Erythorbate

Isoascorbic acid

D-isoascorbic acid