Erythorbic Acid Chemical Properties

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)

vapor pressure 

0Pa at 25℃

FEMA 

2410 | ERYTHROBIC ACID

refractive index 

-17.5 ° (C=10, H2O)

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, clear, colorless to very faintly yellow

pka

4.09±0.10(Predicted)

form 

Crystals or Crystalline Powder

color 

White to slightly yellow

Odor

odorless

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

LogP

-1.69 at 25℃

CAS DataBase Reference

89-65-6(CAS DataBase Reference)

EPA Substance Registry System

Isoascorbic acid (89-65-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

2

RTECS 

KF3015000

TSCA 

Yes

HS Code 

29329990

Hazardous Substances Data

89-65-6(Hazardous Substances Data)

MSDS

• Language:English Provider:2,3-Didehydro-D-erythro-hexono-1,4-lactone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Erythorbic Acid Usage And Synthesis

Chemical Properties

Erythorbic acid occurs as a white or slightly yellow-colored crystals or powder. It gradually darkens in color upon exposure to light.

Uses

Antioxidant (industrial and food), especially in brewing industry, reducing agent in photography.

Uses

Erythorbic Acid is a food preservative that is a strong reducing agent (oxygen accepting) which functions similarly to antioxidants. In the dry crystalline state it 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. It 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. It is used to control oxidative color and flavor deterioration in fruits at 150–200 ppm. It 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%.

Uses

Erythorbic Acid is used as a food additive as an antimicrobial and antioxidative agent.

Definition

ChEBI: D-isoascorbic acid is an ascorbic acid.

Production Methods

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.

Biotechnological Production

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.

Flammability and Explosibility

Non flammable

Pharmaceutical Applications

Erythorbic acid is a stereoisomer of L-ascorbic acid, and is used as an antioxidant in foods and oral pharmaceutical formulations. It has approximately 5% of the vitamin C activity of L-ascorbic acid.

Safety

Erythorbic acid is widely used in food applications as an antioxidant. It is also used in oral pharmaceutical applications as an antioxidant. Erythorbic acid is generally regarded as nontoxic and nonirritant when used as an excipient. Erythorbic acid is readily metabolized and does not affect the urinary excretion of ascorbic acid.
The WHO has set an acceptable daily intake of erythorbic acid and its sodium salt in foods at up to 5 mg/kg body-weight.

storage

Erythorbic 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). [Reichstein et al. Helv max Chim Acta 17 510, 516 1934, Heslop et al. J Chem Soc 225 1944, Beilstein 18 III/IV 3037, 18/5 V 26.]

Incompatibilities

Erythorbic acid is incompatible with chemically active metals such as aluminum, copper, magnesium, and zinc. It is also incompatible with strong bases and strong oxidizing agents.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (oral concentrate and tablets).

Erythorbic Acid(89-65-6)Related Product Information

• Sodium erythorbate
• ε-Caprolactone
• Ascorbyl Palmitate
• ASCORBATE OXIDASE
• 4-Hexanolide
• Polycaprolactone
• Sodium ascorbate
• trans-2-Hexenoic acid
• Folic acid
• L-Fucose
• Ethyl 2-(Chlorosulfonyl)acetate
• Ascorbic Acid
• Alginic acid
• Alginic Sodium Diester
• Glycine
• Citric acid
• (-)-Corey lactone diol
• Erythromycin