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Sigma-Aldrich

(±)-α-Tocopherol phosphate disodium salt

water-soluble α-tocopherol analog

Synonym(s):

Alpha Tocopherol phosphate disodium salt

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About This Item

Linear Formula:
C29H49O5PNa2
CAS Number:
Molecular Weight:
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

Related Categories

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)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A transient treatment of hippocampal neurons with alpha-tocopherol induces a long-lasting protection against oxidative damage via a genomic action
de Jesus Ferreira MC, et al.
Free Radical Biology & Medicine (2005)
Jean-Marc Zingg
Mini reviews in medicinal chemistry, 7(5), 543-558 (2007-05-17)
Natural vitamin E comprises 8 different analogues, the alpha-, beta-, gamma-, and delta-tocopherols and the alpha-, beta-, gamma-, and delta-tocotrienols. However, only alpha-tocopherol is selectively enriched by the liver; the other vitamin E analogues and also excess alpha-tocopherol are converted
Subhendu Mukherjee et al.
Biochimica et biophysica acta, 1782(9), 498-503 (2008-06-17)
The emerging potential of alpha-tocopheryl phosphate, a phosphoric acid ester of alpha-tocopherol, in health benefits was tested gavaging this compound (5 mg/kg body wt) to a group of rats for a period of thirty days while the control rats were
Tomohisa Mori et al.
Behavioural pharmacology, 18(8), 725-729 (2007-11-09)
Chronic morphine-induced withdrawal syndrome after morphine cessation remains a severe obstacle in the clinical treatment of morphine. Previous studies have shown that nitric oxide synthetase (NOS) inhibitors may have therapeutic potential in morphine withdrawal in humans. The mechanisms that underlie
Keiko Nishio et al.
Free radical biology & medicine, 50(12), 1794-1800 (2011-03-30)
α-Tocopheryl phosphate (α-TP), a water-soluble analogue of α-tocopherol, is found in humans, animals, and plants. α-TP is resistant to both acid and alkaline hydrolysis and may exert its own function in this form in vivo. In this study, the uptake

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