D-Isoascorbic Acid

• CAS: 89-65-6
• Catalog Number: ACM89656
• Category: Other Products
• Molecular Weight: 176.12
• Molecular Formula: C6H8O6
• Description: Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer of ascorbic acid (vitamin C). It is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature. It is denoted by E number E315, and is widely used as an Antioxidants in processed foods.Clinical trials have been conducted to investigate aspects of the nutritional value of erythorbic acid.One such trial investigated the effects of erythorbic acid 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 is a potent enhancer of nonheme-iron absorption.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 as a food preservative has increased.It is also used as a preservative in cured meats and frozen vegetables.It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.
• Synonyms: D-Araboascorbic Acid
• IUPAC Name: (2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
• Canonical SMILES: C([C@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O
• 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
• InChI Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N
• Boiling Point: 502.7 °C at 760 mmHg
• Melting Point: 167-172 ºC
• Flash Point: 238.2±23.6 °C
• Density: 2.0±0.1 g/cm3
• Appearance: Crystals
• EC Number: 201-928-0
• Exact Mass: 176.03200
• Hazard Codes: Xi
• Hazard Statements: Xi: Irritant
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• HS Code: 2932209090
• LogP: -1.40740
• PSA: 17.22
• Refractive Index: 1.711
• Safety Description: S24/25
• Stability: Stable. Combustible. Incompatible with chemically active metals, aluminium, zinc, copper, magnesium, strong bases, strong oxidizing agents.
• Storage Conditions: Store at 0-5ºC
• WGK Germany: 2

Synthetic Use

Upstream Synthesis Route 1

• 3445-24-7

• 89-65-6

Reference: [1]Helvetica Chimica Acta,1934,vol. 17,p. 510,519

Upstream Synthesis Route 2

• 21063-40-1

• 89-65-6

Reference: [1]Patent: US2165151,1938,

Downstream Synthesis Route 1

• 77-76-9
• 89-65-6

• 25581-41-3

Reference: [1] Tetrahedron, 2004, vol. 60, # 31, p. 6523 - 6531

Downstream Synthesis Route 2

• 89-65-6

• 15667-21-7

Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 5, p. 1957 - 1958

Downstream Synthesis Route 3

• 89-65-6

• 62-76-0
• 15667-21-7

Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, # 11, p. 3661 - 3672

Downstream Synthesis Route 4

• 89-65-6

• 62-76-0
• 15667-21-7

Reference: [1]Journal of the American Chemical Society,1983,vol. 105,p. 3661 - 3672

* For details of the synthesis route, please refer to the original source to ensure accuracy.