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A7506

Sigma-Aldrich

L-Ascorbic acid

reagent grade, crystalline

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Synonym(s):
L-Threoascorbic acid, Antiscorbutic factor, Vitamin C
Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
50-81-7
Molecular Weight:
176.12
Beilstein:
84272
EC Number:
200-066-2
MDL number:
MFCD00064328
PubChem Substance ID:
24891246
NACRES:
NA.26

biological source

synthetic

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)

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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

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.
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.

Caution

May darken in storage.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Takashi Yoshida et al.
Nature chemical biology, 2(11), 596-607 (2006-09-26)
Transient receptor potential (TRP) proteins form plasma-membrane cation channels that act as sensors for diverse cellular stimuli. Here, we report a novel activation mechanism mediated by cysteine S-nitrosylation in TRP channels. Recombinant TRPC1, TRPC4, TRPC5, TRPV1, TRPV3 and TRPV4 of
Noriko Umegaki-Arao et al.
Science translational medicine, 6(264), 264ra164-264ra164 (2014-11-28)
Revertant mosaicism is a naturally occurring phenomenon involving spontaneous correction of a pathogenic gene mutation in a somatic cell. It has been observed in several genetic diseases, including epidermolysis bullosa (EB), a group of inherited skin disorders characterized by blistering
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