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A5960

Sigma-Aldrich

L-Ascorbic acid

BioXtra, ≥99.0%, crystalline

Synonym(s):

L-Threoascorbic acid, Antiscorbutic factor, Vitamin C

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About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
50-81-7
Molecular Weight:
176.12
Beilstein/REAXYS Number:
84272
EC Number:
200-066-2
MDL number:
MFCD00064328
UNSPSC Code:
12352209
PubChem Substance ID:
24891042
NACRES:
NA.26

product line

BioXtra

Quality Level

200

assay

≥99.0%

form

crystalline

technique(s)

cell culture | mammalian: suitable

impurities

≤0.0005% Phosphorus (P)
≤0.1% Insoluble matter

ign. residue

≤0.1%

color

white to off-white

pH

1.0-2.5 (25 °C, 176 g/L in water)

mp

190-194 °C (dec.)

solubility

H2O: 0.5 M, clear, colorless

anion traces

sulfate (SO42-): ≤0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

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

Ascorbic acid is also referred to as Vitamin C. It contains a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Vitamin C is a water-soluble vitamin. Vitamin C is a part of citrus fruits, such as Indian gooseberry, broccoli, strawberries, brussels sprouts. L-ascorbic acid is the biologically active form of ascorbic acid. It is unstable and hydrophilic. Ascorbic acid carries a neutral charge, which gets converted to ascorbate by protonation.

Application

  • L-Ascorbic acid has been used to induce osteoblast differentiation from primary bone marrow cultures.
  • It has been used for the differentiation of hCMPCs (human cardiomyocyte progenitor cells) into cardiomyocytes.
  • It has been used to measure the mitochondrial electron transport chain (complex IV) activity.

Biochem/physiol Actions

L-Ascorbic acid plays a role in production of neurotransmitters, carnitine and collagen synthesis. 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. Vitamin C exhibits anti-oxidant properties. Vitamin C is implicated in conferring protection against photoaging and anti-aging. Deficiency of vitamin C is associated with scurvy, bleeding gums, poor wound healing, anemia and muscle degeneration.

Caution

May darken in storage.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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Vitamin C as an antioxidant: evaluation of its role in disease prevention.
Padayatty SJ et al.
Journal of the American College of Nutrition, 22, 18-18 (2003)
Increased mitochondrial electron transport chain activity at complex I is regulated by N-acetylcysteine in lymphocytes of patients with systemic lupus erythematosus.
Doherty E et al.
Antioxidants & Redox Signaling, 21, 56-56 (2014)
CCN3 impairs osteoblast and stimulates osteoclast differentiation to favor breast cancer metastasis to bone.
Ouellet V et al.
The American Journal of Pathology, 178, 2377-2377 (2011)
Dandan Liang et al.
PloS one, 9(7), e103097-e103097 (2014-07-30)
microRNAs (miRNAs) play essential roles in cardiogenesis. The altered expression of miRNAs can result in cardiac malformations by inducing abnormalities in the behavior of cardiac cells. However, the role of miR-10a in the regulation of cardiomyocyte progenitor cells (CMPCs) remains
Vitamin C in health and disease: its role in the metabolism of cells and redox state in the brain
Figueroa M R and Rivas A S
Frontiers in Physiology, 6(4), 397-397 (2015)
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