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D-α-Tocopherol polyethylene glycol 1000 succinate

BioXtra, water soluble vitamin E conjugate

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Synonym(s):
D-α-Tocopherol polyethylene glycol succinate, TPGS, Vitamin E polyethylene glycol succinate, Vitamin E-TPGS
CAS Number:
MDL number:
eCl@ss:
34058007
NACRES:
NA.79

biological source

synthetic

product line

BioXtra

form

powder, crystals or chunks

composition

α-tocopherol, ≥25%

concentration

≥25% (ALPHA TOCOPHEROL)

color

white to light brown

mp

>36 °C

solubility

H2O: 1 g/10 mL, clear to faintly turbid, colorless to faintly yellow

cation traces

Al: ≤5 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤5 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

storage temp.

2-8°C

InChI

1S/C35H58O6/c1-24(2)12-9-13-25(3)14-10-15-26(4)16-11-20-35(8)21-19-30-29(7)33(27(5)28(6)34(30)41-35)40-32(38)18-17-31(37)39-23-22-36/h24-26,36H,9-23H2,1-8H3

InChI key

AOBORMOPSGHCAX-UHFFFAOYSA-N

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1 of 4

This Item
T3126T325190669
(±)-α-Tocopherol synthetic, ≥96% (HPLC)

Sigma-Aldrich

T3251

(±)-α-Tocopherol

-
(±)-α-Tocopherol tested according to Ph. Eur.

Sigma-Aldrich

90669

(±)-α-Tocopherol

-
form

powder, crystals or chunks

form

powder

form

liquid

form

liquid

concentration

≥25% (ALPHA TOCOPHEROL)

concentration

-

concentration

-

concentration

-

color

white to light brown

color

white to yellow

color

faint brown to brown, yellow to very dark yellow

color

tan

mp

>36 °C

mp

-

mp

-

mp

2.5-3.5 °C

solubility

H2O: 1 g/10 mL, clear to faintly turbid, colorless to faintly yellow

solubility

-

solubility

H2O: insoluble, acetone: miscible, chloroform: miscible, ethanol: miscible, vegetable oils: miscible

solubility

-

General description

Tocofersolan, also known as Vitamin E-TPGS, is a nonionic surfactant and a synthetic polyethylene glycol derivative of α-tocopherol, commonly known as vitamin E. This water-soluble amphipathic formulation consists of d-alpha-tocopherol succinate coupled to polyethylene glycol (PEG) 1000 through a succinate linker. Its amphipathic nature enables the formation of micelles, facilitating uptake into enterocytes, even in the absence of bile salts. Upon hydrolysis, fat-soluble d-alpha-tocopherol is released. Tocofersolan significantly improves the absorption of d-alpha-tocopherol compared to free administration.

Moreover, Tocofersolan acts as an inhibitor of P-glycoprotein (P-gp or MDR1) substrate-induced ATPase activity in cell-free assays. It has demonstrated efficacy against resistant K562 cells by binding to urokinase-type plasminogen activator, a crucial enzyme for cancer cell migration and invasion. Additionally, Tocofersolan inhibits tyrosine kinase, a key player in cancer cell development, offering potential applications in metabolomics and biochemical research. Its ability to enhance the absorption of water-insoluble agents and other fat-soluble vitamins positions it as a promising compound for formulation and drug delivery research.

Application

D-α-Tocopherol polyethylene glycol 1000 succinate has been used as an emulsifier in the preparation of Poly(lactic-co-glycolic acid) (PLGA) particle as synthetic DNA carriers by double emulsion (w1/o/w2) and nanoprecipitation method.
D-α-Tocopherol polyethylene glycol 1000 is a versatile compound that finds application in cell biology, metabolomics, biochemical and drug delivery research.

Biochem/physiol Actions

D-α-Tocopherol polyethylene glycol 1000 succinate (TPGS) also known as vitamin E TPGS, is a therapeutic agent for vitamin E deficiency in children, administered during chronic childhood cholestasis. TPGS exerts anti-tumor activity in MCF-7 and breast cancer cells by downregulating anti-apoptotic proteins. TPGS finds its application as an emulsifier in the preparation of poly(lactic-co-glycolic acid) (PLGA) particles for DNA labelling, produces particles of uniform size, high encapsulation efficiency, increases hydrophilicity and prevents aggregation of particles.
Tocopherols (TCP) (vitamin E) are a series (α, α, α and α) 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.

Tocopherol polyethylene glycol 1000 succinate (TPGS) may be used to create biodegradable polymers and antioxidant surfactants.
TPGS exerts anti-tumor activity in MCF-7 and breast cancer cells by downregulating anti-apoptotic proteins.
TPGS finds its application as an emulsifier in the preparation of poly(lactic-co-glycolic acid) (PLGA) particles for DNA labelling, produces particles of uniform size, high encapsulation efficiency, increases hydrophilicity and prevents aggregation of particles.

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

392.0 °F

Flash Point(C)

> 200 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis, characterization, and in-vitro antitumor activity of the polyethylene glycol (350 and 1000) succinate derivatives of the tocopherol and tocotrienol isomers of Vitamin E
Abu-Fayyad A and Nazzal S
International Journal of Pharmaceutics, 519(1-2), 145-156 (2017)
Liyan Zhao et al.
Journal of biomedical nanotechnology, 7(3), 358-365 (2011-08-13)
The objective of this study was to develop a polymeric delivery system to improve the solubility and biological activity of Quercetin (QT). QT loaded mixed micelles, composed of Pluronic P123 (P123) and D-a-tocopheryl polyethylene glycol succinate (TPGS) with proportion of
Anandhkumar Raju et al.
Expert opinion on drug delivery, 10(6), 747-760 (2013-03-06)
In this study, the authors developed D-α-tocopheryl polyethylene glycol 1000 succinate (vitamin E TPGS or simply TPGS) liposomes and further conjugated them to trastuzumab for controlled and targeted delivery of docetaxel (DTX) as a model hydrophobic drug. DTX- or coumarin-6-loaded
Heni Rachmawati et al.
Journal of pharmaceutical sciences, 102(1), 204-214 (2012-10-11)
Curcumin, a naturally occuring polyphenolic phytoconstituent, is isolated from the rhizomes of Curcuma longa Linn. (Zingiberaceae). It is water insoluble under acidic or neutral conditions but dissolves in alkaline environment. In neutral or alkaline conditions, curcumin is highly unstable undergoing
Christiana M Neophytou et al.
Biochemical pharmacology, 89(1), 31-42 (2014-02-25)
D-alpha-tocopheryl polyethylene glycol succinate (TPGS) is a vitamin E derivative that has been intensively applied as a vehicle for drug delivery systems to enhance drug solubility and increase the oral bioavailability of anti-cancer drugs. Recently, it has been reported that

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