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Merck

T2020

Sigma-Aldrich

(±)-α-Tocopherol phosphate disodium salt

water-soluble α-tocopherol analog

Sinónimos:

Alpha Tocopherol phosphate disodium salt

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About This Item

Fórmula lineal:
C29H49O5PNa2
Número de CAS:
Peso molecular:
554.65
MDL number:
UNSPSC Code:
12352205
eCl@ss:
34058016
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

assay

≥97% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

2-8°C

SMILES string

[Na].CC(C)CCCC(C)CCCC(C)CCCC1(C)CCc2c(C)c(OP(O)(O)=O)c(C)c(C)c2O1

InChI

1S/C29H51O5P.Na.H/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(34-35(30,31)32)23(5)24(6)28(26)33-29;;/h20-22H,9-19H2,1-8H3,(H2,30,31,32);;

InChI key

QRLCTLIPEFQSSG-UHFFFAOYSA-N

Application

(±)-α-Tocopherol phosphate disodium salt has been used as an antioxidant, to assess its protection against oxidative damage in rat hippocampal neurons. It has also been used to study its molecular mechanisms and transport across the plasma membrane.

Biochem/physiol Actions

Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by Homo sapiens. α-Tocopherol phosphate (TocP) is used along the α-tocopherol acetate, α-tocopherol-nicotinate, α-tocopherol succinate and other esterified forms as a vitamin E supplement with similar but differential activities.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Jean-Marc Zingg et al.
Free radical biology & medicine, 49(12), 1989-2000 (2010-10-07)
The natural vitamin E analog α-tocopheryl phosphate (αTP) modulates atherosclerotic and inflammatory events more efficiently than the unphosphorylated α-tocopherol (αT). To investigate the molecular mechanisms involved, we have measured plasma levels of αTP and compared the cellular effects of αT
Adriana Sampayo-Reyes et al.
Acta biochimica Polonica, 53(3), 547-552 (2006-10-05)
Human glutathione S-transferase omega 1-1 (hGSTO1-1) is a newly identified member of the glutathione S-transferase (GST) family of genes, which also contains alpha, mu, pi, sigma, theta, and zeta members. hGSTO1-1 catalyzes the reduction of arsenate, monomethylarsenate (MMA(V)), and dimethylarsenate
Yesim Negis et al.
IUBMB life, 57(1), 23-25 (2005-07-23)
The finding that alpha-tocopheryl phosphate is present in cells in small amounts, that it can be synthesized and hydrolyzed supports the hypothesis that alpha-tocopheryl phosphate might be a signaling molecule. The possible pathways needed for the synthesis, hydrolysis and signaling
R Libinaki et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 44(7), 916-932 (2005-12-13)
The safety of a formulation of mixed tocopheryl phosphates, (MTP) was evaluated in a series of toxicological tests in vivo using rats, mice and rabbits and in vitro using bacterial and mammalian cell cultures. The tests conducted included an oral
Jean-Marc Zingg et al.
Molecular nutrition & food research, 54(5), 679-692 (2010-02-20)
The vitamin E (alpha-tocopherol, alphaT) derivative, alpha-tocopheryl phosphate (alphaTP), is detectable in small amounts in plasma, tissues, and cultured cells. Studies done in vitro and in vivo suggest that alphaT can become phosphorylated and alphaTP dephosphorylated, suggesting the existence of

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