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molecular formula C6H8O6 B605621 l-ascorbic acid CAS No. 50-81-7

l-ascorbic acid

Cat. No. B605621
M. Wt: 176.12 g/mol
InChI Key: CIWBSHSKHKDKBQ-JLAZNSOCSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04845246

Procedure details

6-O-(2-keto-L-gulonoyl)-L-ascorbate substantially free from 2-keto-L-gulonic acid, 1.2 g (3.4 mmol), was dissolved in 50 ml of water, to which 1.4 g (17 mmol) of sodium hydrogencarbonate was added and stirred at 40° C. for about 1.5 hours. High performance liquid chromatography analysis of the reaction mixture showed that 1.14 g (yield: 95.2%) of L-ascorbic acid was present with 0.07 g of 2-keto-L-gulonic acid but the starting substance 6-O-(2-keto-L-gulonoyl)-L-ascorbate was not found. Condition of high performance liquid chromatography:
[Compound]
Name
6-O-(2-keto-L-gulonoyl)-L-ascorbate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
1.4 g
Type
reactant
Reaction Step One
Name
Quantity
50 mL
Type
solvent
Reaction Step One
Yield
95.2%

Identifiers

REACTION_CXSMILES
[CH2:1]([OH:13])[C@H:2]([OH:12])[C@@H:3](O)[C@H:4]([OH:10])[C:5]([C:7]([OH:9])=[O:8])=[O:6].C(=O)([O-])O.[Na+]>O>[O:8]=[C:7]1[O:9][C@H:3]([C@H:2]([CH2:1][OH:13])[OH:12])[C:4]([OH:10])=[C:5]1[OH:6] |f:1.2|

Inputs

Step One
Name
6-O-(2-keto-L-gulonoyl)-L-ascorbate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([C@@H]([C@H]([C@@H](C(=O)C(=O)O)O)O)O)O
Name
Quantity
1.4 g
Type
reactant
Smiles
C(O)([O-])=O.[Na+]
Name
Quantity
50 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
40 °C
Stirring
Type
CUSTOM
Details
stirred at 40° C. for about 1.5 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added

Outcomes

Product
Details
Reaction Time
1.5 h
Name
Type
product
Smiles
O=C1C(O)=C(O)[C@H](O1)[C@@H](O)CO
Measurements
Type Value Analysis
AMOUNT: MASS 1.14 g
YIELD: PERCENTYIELD 95.2%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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