Showing Compound D-Isoascorbic acid (FDB012005)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2018-05-28 23:33:15 UTC

Primary ID

FDB012005

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Isoascorbic acid

Description

Production from glucose by Penicillium subspecies Antioxidant for foods and soft drinks. Flavouring ingredient; colouring preservative/antioxidant in fruit and meat products Erythorbic acid, formerly known as isoascorbic acid and D-araboascorbic acid, is a stereoisomer of ascorbic acid (vitamin C). It is a vegetable-derived food additive produced from sucrose. It is denoted by E number E315, and is widely used as an antioxidant in processed foods. [Wikipedia].

CAS Number

89-65-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Ascorbate	Generator
D-(-)-isoascorbic acid	biospider
D-Araboascorbic acid	manual
D-erythorbic acid	biospider
D-erythro-3-Ketohexonic acid lactone	biospider
D-erythro-3-Oxohexonic acid lactone	biospider
D-erythro-ascorbic acid	biospider
D-erythro-Hex-2-enoic acid gamma-lactone	biospider
D-erythro-hex-2-enonic acid gamma-lactone	biospider
D-erythro-hex-2-enono-1,4-lactone	biospider
D-isoascorbic acid	biospider
E315	db_source
FEMA 2410	db_source
Isovitamin C	manual

Predicted Properties

Property	Value	Source
Water Solubility	245 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	15.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H8O6

IUPAC name

5-(1,2-dihydroxyethyl)-3,4-dihydroxy-2,5-dihydrofuran-2-one

InChI Identifier

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

InChI Key

CIWBSHSKHKDKBQ-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C1OC(=O)C(O)=C1O

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

Classification

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 40.92%; H 4.58%; O 54.50%	DFC
Melting Point	Mp 168° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	400 mg/mL at 25 oC	MERCK INDEX (1996)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -22 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9600000000-7805023a343f9125f687	Spectrum
Predicted GC-MS	Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascorbic acid, TBDMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kdi-1900000000-6fc1f52dff15c8ef305f	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06tf-5900000000-85998d0acb31a7ab3c56	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-cd1037225892d74b0ccf	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0mmi-1900000000-51afc755ee499f1a5ac5	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0cfr-3900000000-9dd2e63d3df9f18e97ef	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-49057d03930aad882728	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-a9c05371c96e57620f6d	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-751cf542b64b645b35bd	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052n-9000000000-1b9f60ef905d0b091c5f	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-ca66949653f372cd33a3	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9000000000-bd3e23ffd81ac3d88ca3	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-8fd8a9cdbcb1b116e3ca	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6981

Pubchem Substance ID

Not Available

ChEBI ID

51438

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BWQ58-F:HCL84-P

EAFUS ID

1115

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1019901

SuperScent ID

Not Available

Wikipedia ID

Erythorbic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference