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Merck

A7506

L-Ascorbic acid

reagent grade, crystalline

Synonym(s):

L-Threoascorbic acid, Antiscorbutic factor, Vitamin C

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About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
Molecular Weight:
176.12
UNSPSC Code:
12352209
NACRES:
NA.26
PubChem Substance ID:
EC Number:
200-066-2
Beilstein/REAXYS Number:
84272
MDL number:
Assay:
≥98% ( with iodine, titration)
Form:
crystalline
Grade:
reagent grade
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biological source

synthetic

Quality Level

grade

reagent grade

assay

≥98% ( with iodine, titration)

form

crystalline

technique(s)

HPLC: suitable, cell culture | stem cell: suitable

color

white to slightly yellow

pH

1.0-2.5 (25 °C, 176 g/L in water)

mp

190-194 °C (dec.)

solubility

water: soluble 50 mg/mL

storage temp.

room temp

SMILES string

OC([C@]([C@@H](O)CO)([H])O1)=C(O)C1=O

InChI

1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

InChI key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Gene Information

human ... SLC23A2(9962)

General description

L-Ascorbic acid biosynthetic pathway varies in plants, animals and fungi. It is synthesized from L-gulono-1,4-lactone by the action of enzyme L-gulono-1,4-lactone oxidase (GLO).

Application

L-Ascorbic acid has been used:
  • as a chondrogenic medium component for culturing bone-derived mesenchymal stem cells (BMSCs)(149)
  • as a reference standard in high-performance liquid chromatography system (HPLC)(150)
  • to test its effect on human gastric cancer GES-1 and AGS cells(151)

Biochem/physiol Actions

L-Ascorbic acid deficiency is associated with lack of L-gulono-1,4-lactone oxidase (GLO) enzyme. It elicits antioxidant functionality and gets oxidized to dehydroascorbate via ascorbyl radical intermediate. L-Ascorbic acid is essential for maintaining the redox balance. It is a cofactor for dopamine-β-hydroxylase and favors T cell proliferation, protects immune system and provides relief in common cold.
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Disclaimer

May darken in storage.


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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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L-Ascorbic acid in organic synthesis: an overview
Tripathi RP, et al.
Current Organic Chemistry, 13(1), 99-122 (2009)
Vitamin C in health and disease: its role in the metabolism of cells and redox state in the brain
Figueroa-Mendez R and Rivas-Arancibia, S
Frontiers in Physiology, 6, 397-397 (2015)
Vitamin C in disease prevention and cure: an overview
Chambial S, et al.
Indian Journal of Clinical Biochemistry : IJCB, 28(4), 314-328 (2013)