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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:
60934-46-5
Molecular Weight:
554.65
MDL number:
MFCD00079579
UNSPSC Code:
12352205
eCl@ss:
34058016
PubChem Substance ID:
24900007
NACRES:
NA.79

Key Documents

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biological source

synthetic (organic)

Quality Level

300

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000498287
0000498287
0000497195
0000497195
0000487456

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Jean-Marc Zingg et al.
BioFactors (Oxford, England), 38(1), 24-33 (2012-01-28)
Vitamin E was originally discovered as a dietary factor essential for reproduction in rats. Since then, vitamin E has revealed many important molecular properties such as the scavenging of reactive oxygen and nitrogen species or the modulation of signal transduction
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
Satomi Nakayama et al.
The Journal of investigative dermatology, 121(2), 406-411 (2003-07-26)
The ability of the novel water-soluble provitamin E, alpha-tocopherol-6-O-phosphate, to protect against ultraviolet B-induced damage in cultured mouse skin was investigated and compared with the protectiveness of alpha-tocopherol acetate in cultured mouse skin. Pretreatment of skin with 0.5% (9.4 mM)
Molecular mechanism of alpha-tocopheryl-phosphate transport across the cell membrane
Negis Y, et al.
Biophysical Chemistry (2007)
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
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