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A7506

L-Ascorbic acid

Name: <SC>L</SC>-Ascorbic acid
Brand: SIGMA

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:

50-81-7

Molecular Weight:

176.12

UNSPSC Code:

12352209

NACRES:

NA.26

PubChem Substance ID:

24891246

EC Number:

200-066-2

Beilstein/REAXYS Number:

84272

MDL number:

MFCD00064328

Assay:

≥98% ( with iodine, titration)

Form:

crystalline

Grade:

reagent grade

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biological source

synthetic

Quality Level

200

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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Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Coenzymes

Proteins & Enzymes

Vitamins

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.

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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Certificates of Analysis (COA)

Lot/Batch Number

0000548748

0000517323

0000517324

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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)

L-Ascorbic acid in organic synthesis: an overview

Tripathi RP, et al.

Current Organic Chemistry, 13(1), 99-122 (2009)

Vitamin C in disease prevention and cure: an overview

Chambial S, et al.

Indian Journal of Clinical Biochemistry : IJCB, 28(4), 314-328 (2013)

Nitric oxide activates TRP channels by cysteine S-nitrosylation.

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

Induced pluripotent stem cells from human revertant keratinocytes for the treatment of epidermolysis bullosa.

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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Global Trade Item Number

SKU	GTIN
A7506-25G	04061835542529
A7506-500G	04061835542536
A7506-100G	04061835542505
A7506-5KG	04061835542543
A7506-1KG	04061835542512

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