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L-Ascorbic acid 2-phosphate

Names

[ CAS No. ]:
23313-12-4

[ Name ]:
L-Ascorbic acid 2-phosphate

[Synonym ]:
Ascorbate-2-phosphate
2-phospho-L-ascorbic acid
2-O-phosphonohex-1-enofuranos-3-ulose
L-Ascorbate 2-monophosphate
ascorbic acid-2-phosphoric acid ester
L-ascorbic acid 2-O-phosphate
ascorbic acid 2-phosphate

Biological Activity

[Description]:

L-ascorbic acid 2-phosphate (2-Phospho-L-ascorbic acid) is a long-acting vitamin C derivative that can stimulate collagen formation and expression[1]. L-ascorbic acid 2-phosphate (2-Phospho-L-ascorbic acid) can be used as a culture medium supplement for the osteogenic differentiation of human adipose stem cells (hASCs). L-ascorbic acid 2-phosphate increases alkaline phosphatase (ALP) activity and expression of runx2A in hASCs during the osteogenic differentiation[2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Metabolic Disease

[Target]

IC50: alkaline phosphatase (ALP); collagen formation; runx2A[2][3]


[In Vitro]

L-Ascorbic acid 2-phosphate (0.1-1.5 mM; 2 to 3 weeks with medium exchange every 2 to 3 days) significantly stimulates cell growth, whereas addition of l-Ascorbic acid (Asc)  achieves only weak growth stimulation. A combination of Asc-2P and bFGF significantly increases cell growth, but supplementation with EGF and/or insulin does not have any additional effect [1]. L-Ascorbic acid 2-phosphate (50 µM-250 µM) is needed for the effective osteogenic differentiation of human adipose stem cells (hASCs), and higher concentrations of AsA2-P results in increased runx2 expression and ALP activity. The highest proliferation, ALP activity and runx2 expression is achieved with 150 µM AsA2-P and 10 nM dexamethasone (Dex), and 250 µM AsA2-P and 5 nM Dex[3]. Cell Proliferation Assay[1] Cell Line: Human corneal endothelial cells (HCECs)  Concentration: 0.1 mM; 0.3 mM; 1.5 mM Incubation Time: 2 to 3 weeks with medium exchange every 2 to 3 days Result: Stimulated HCEC cells growth.

[References]

[1]. Shima N, et al. Increased proliferation and replicative lifespan of isolated human corneal endothelial cells with L-ascorbic acid 2-phosphate.Invest Ophthalmol Vis Sci. 2011 Nov 7;52(12):8711-7.

[2]. Kurata S, et al. Epidermal growth factor inhibits transcription of type I collagen genes and production of type I collagen in cultured human skin fibroblasts in the presence and absence of L-ascorbic acid 2-phosphate, a long-acting vitamin C derivative.J Biol Chem. 1991 May 25;266(15):9997-10003.

[3]. Kyllönen L, et al. Effects of different serum conditions on osteogenic differentiation of human adipose stem cells in vitro.Stem Cell Res Ther. 2013 Feb 15;4(1):17.

Chemical & Physical Properties

[ Density]:
2.01 g/cm3

[ Boiling Point ]:
561.3ºC at 760 mmHg

[ Molecular Formula ]:
C6H9O9P

[ Molecular Weight ]:
256.10400

[ Flash Point ]:
293.2ºC

[ Exact Mass ]:
255.99800

[ PSA ]:
163.56000

[ Vapour Pressure ]:
6.19E-15mmHg at 25°C

[ Index of Refraction ]:
1.629

Synthetic Route

Precursor & DownStream


Related Compounds