L-Ascorbic acid

Specifications

Purity

≥99% (Assay)

Appearance

White to off-white powder

Identity

1H-NMR

Properties

Solvents

water (50 mg/ml) or DMSO (10 mg/ml) .

Melting Point

190-194 °C (dec.)

Shipping

AMBIENT

Short Term Storage

RT

Long Term Storage

RT

Handling Advice

Protect from light and moisture.

Use / Stability

Stable for at least 2 years after receipt when stored at RT.

Transportation

Not dangerous goods

Description

L-Ascorbic acid (better known as Vitamin C) is a naturally occurring electron donor and therefore serves as a reducing agent. It is synthesized from glucose in the liver of most mammalian species, excluding humans, non-human primates, or guinea pigs who must obtain it through dietary consumption. In humans, L-Ascorbic acid acts as an electron donor for eight different enzymes, including those related to collagen hydroxylation, carnitine synthesis (which aids in the generation of adenosine triphosphate), norepinephrine synthesis, tyrosine metabolism and amidating peptides. L-Ascorbic acid demonstrates antioxidant activity that may be of some benefit for reducing the risk of developing chronic diseases such as cancer, cardiovascular disease, and cataracts. L-Ascorbic acid is an inhibitor of Cav3.2 channels, but displays no effect on Cav3.1 or Cav3.3 channels heterologously expressed in HEK 293 cells. L-Ascorbic acid enhances the generation of induced pluripotent stem cells (iPSCs) from mouse and human somatic cells by increasing reprogramming efficiency. It is also a commonly used antifade reagent in live cell microscopy. Ascorbate has critical roles in the central nervous system (CNS), it is a neuromodulator of glutamatergic, cholinergic, dopaminergic and γ-aminobutyric acid (GABA)-ergic neurotransmission, provides support and structure to neurons, and participates in processes such as differentiation, maturation and survival of neurons. L-Ascorbic acid is essential to stimulate the immune system. Its immunostimulant, anti-inflammatory, antiviral and antibacterial properties are well known. Due to its effects and diversity of regulated pathways, L-Ascorbic acid is suitable for use in various fields of medicine including immunology, toxicology, radiobiology and is co-applied as an adjuvant to regulate immunity, gene expression and other important physiological processes.

Smiles

OC1=C(O)[C@]([C@@H](O)CO)([H])OC1=O

InChi Key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

References

(1) S. Englard & S. Seifter, Ann. Rev. Nutr. 6, 365 (1986) (Review) , (2) B. Peterkofsky, Am. J. Clin. Nutr. 54, 1135S (1991) , (3) C.J. Rebouche, Am. J. Clin. Nutr. 54, 1147S (1991) , (4) E.J. Diliberto, et al., Am. J. Clin. Nutr. 54, 1163S (1991) , (5) S.J. Padayatty, et al., J. Am. Coll. Nutr. 22, 18 (2003) , (6) S.S. Gropper, et al., Adv. Nutr. Human Metab. 4, 259 (2005) , (7) M.T. Nelson, et al., J. Neurosci. 27, 12577 (2007) , (8) M.A. Esteban, et al., Cell Stem Cell 6, 71 (2010) , (9) T. Cordes, et al., Phys. Chem. Chem. Phys. 13, 6699 (2011) , (10) A. Sorice, et al., Mini Rev. Med. Chem. 14, 444 (2014) (Review) , (11) M. Moretti, et al., CNS Drugs 31, 571 (2017) (Review) , (12) R. Bakalova, et al., Oxid. Med. Cell Longev. 2020, 1504048 (2020) (Review) , (13) D. Njus, et al., Free Radic. Biol. Med. 159, 37 (2020) (Review)

InChi

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