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A5960

Sigma-Aldrich

L-Ascorbic acid

BioXtra, ≥99.0%, crystalline

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

product line

BioXtra

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.

related product

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Is L-ascorbic acid, Product A5960, the same as vitamin C?

    Yes, L-ascorbic acid is a synonym for vitamin C.

  4. What is the solution stability of L-ascorbic acid, Product A5960?

    Aqueous solutions are stable only in the absence of oxygen.  Aqueous solutions are most stable at pH 5-6, very unstable at alkaline pH. (Data for Biochemical Research, 3rd ed., Dawson, R. M. C., et al., Oxford University Press (New York, NY: 1986), p. 116)  Degradation is markedly increased in the presence of transition metal ions, especially Cu(II) and Fe(III).  The first stage of oxidation of L-ascorbic acid to dehydroascorbic acid is reversible and the biological activity is retained.  Further oxidation to 2,3-diketogulonic acid is not reversible and the activity is lost. (Omura, H., and Yamafuji, K., in Methodicum Chimicum, 11(2), Korte, F., and Goto, M., eds., Academic Press (New York, NY: 1977), p. 115).

  5. What is the pKa of L-ascorbic acid, Product A5960?

    The pKa values for L-ascorbic acid (from the chemicals encyclopedia published by the Royal Society of Chemistry) are 4.17 and 11.57.

  6. What is the extinction coefficient of L-ascorbic acid, Product A5960?

    According to the Data for Biochemical Research, 3rd ed., Dawson, R. M. C., et al., Oxford University Press (New York, NY 1986), p. 116, the L-ascorbic acid extinction coefficient: EmM = 7.0 (265 nm, water), 7.5 (245 nm, acid).

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  9. My question is not addressed here, how can I contact Technical Service for assistance?

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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
Topical vitamin C and the skin: mechanisms of action and clinical applications
Al-Niaimi F and Chiang N Y Z
The Journal of Clinical and Aesthetic Dermatology, 10(7), 14-14 (2017)

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