D-(-)-Isoascorbic acid - analytical standard , CAS No.89-65-6

CAS: 89-65-6 Cat. No.: I109584 Formula: C₆H₈O₆ Molecular Weight: 176.12 Beilstein Registry Number: 84271 EC Number: 201-928-0

GRADE & PURITY Analytical standard

Synonyms

Glucosaccharonic acid|D-erythro-3-Ketohexonic acid lactone|D-soascorbic acid|Erythorbic acid [NF]|FEMA Number: 2410|ISOASCORBIC ACID [MI]|ERYTHORBIC ACID [II]|ISOASCORBIC-ACID|BENZENEACETIC ACID, .ALPHA.-ETHYL-2-(2-(DIETHYLAMINO)ETHOXY)ETHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)|dimethyl-t-butylchlorosilane|(R)-5-((R)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one|13-Oxo-3,6,9,12-tetraoxapentadec-14-en-1-yl acrylate #|Araboascorbic acid|ERYTHORBIC ACID [FHFI]|Neo-cebicure|3-Oxohexonic acid lactone, D-erythro-|D-erythro-Hex-2-enoic acid gamma-lactone|2,3-Didehydro-D-erythro-hexono-1,4-lactone|ASCORBIC ACID IMPURITY F [EP IMPURITY]|D-(-)-Isoascorbic acid|Erythroascorbic acid, D-|D-erythro-3-Oxohexonic acid lactone|(5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one|D-erythro-hex-2-enonic acid gamma-lactone|INS NO.315|Saccharosonic acid|Hex-2-enonic acid gamma-lactone, D-erythro-|(5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (D-Isoascorbic Acid); Ascorbic Acid Impurity F; Sodium Ascorbate Impurity F|D-Isoascorbic acid|d-iso-ascorbic acid|2-(3-chloro-2-methyl-anilino)pyridine-3-carboxylic acid|Erycorbin|D-ASCORBIC ACID, ISO|Erythorbic acid|ERYTHORBIC ACID [USP-RS]|D-Araboascorbic acid|ERYTHORBIC ACID [FCC]|ERYTHORBIC ACID [MART.]|ERYTHORBIC ACID [HSDB]|(5R)-5-((1R)-1,2-DIHYDROXYETHYL)-3,4-DIHYDROXYFURAN-2(5H)-ONE|D-Erythro-hex-2-enonic acid, gamma-lactone,|methyl [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamate|D-erythro-Hex-2-enonic acid, .gamma.-lactone|D-Erythorbic acid|D-erythro-Hex-2-enonic acid, g-lactone|(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 (non-preferred name)|ERYTHORBIC ACID [INCI]|(5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one|D(-)-Isoascorbic Acid (Erythorbic Acid)|ERYTHORBATE|3-Keto-D-erythro-hexonic acid gamma-lactone|(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one|Isoascorbic acid|Mercate 5

Storage

Protected from light,Room temperature

Shipped In

Normal

Specifications

Synonyms

Glucosaccharonic acid | D-erythro-3-Ketohexonic acid lactone | D-soascorbic acid | Erythorbic acid [NF] | FEMA Number: 2410 | ISOASCORBIC ACID [MI] | ERYTHORBIC ACID [II] | ISOASCORBIC-ACID | BENZENEACETIC ACID, .ALPHA.-ETHYL-2-(2-(DIETHYLAMINO)ETHOXY)ETHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1) | dimethyl-t-butylchlorosilane Show more

Specifications & Purity

analytical standard

Storage

Protected from light,Room temperature

Shipped In

Normal

Grade

Analytical standard

Names and Identifiers

Pubchem Sid

528764023

Canonical Smiles

C(C(C1C(=C(C(=O)O1)O)O)O)O

IUPAC Name

(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one

InChIKey

CIWBSHSKHKDKBQ-DUZGATOHSA-N

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

Isomeric SMILES

C([C@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O

WGK Germany

2

RTECS

KF3015000

Molecular Weight

176.12

Beilstein

84271

Reaxy-Rn

84270

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=84270&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Dihydrofurans
      • Subclass Furanones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Dihydrofurans
• Subclass: Furanones
• Intermediate Tree Nodes: Not available
• Direct Parent: Butenolides
• Alternative Parents: Vinylogous acids Enoate esters Secondary alcohols Lactones Enediols 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 2-furanone - Vinylogous acid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - 1,2-diol - Carboxylic acid ester - Enediol - Secondary alcohol - Lactone - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organic oxide - Primary alcohol - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
• External Descriptors: ascorbic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light sensitive.
• x_specific_rotation: -17.5 ° (C=10, H2O)
• x_melt_point_char: 166-172°C
• Molecular Weight: 176.120 g/mol
• XLogP3: -1.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 176.032 Da
• Monoisotopic Mass: 176.032 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 232.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1