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Sigma-Aldrich

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:
UNSPSC Code:
12352205
eCl@ss:
34058007
NACRES:
NA.79

biological source

synthetic

Quality Level

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

SMILES string

CC1=C(C(=C(C2=C1OC(CC2)(C)CCCC(C)CCCC(C)CCCC(C)C)C)OC(=O)CCC(=O)OCCO)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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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

Other Notes

For additional information on our range of Biochemicals, please complete this form.

wgk_germany

WGK 2

flash_point_f

>392.0 °F

flash_point_c

> 200 °C

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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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
Yogesh B Pawar et al.
International journal of pharmaceutics, 436(1-2), 617-623 (2012-07-31)
The clinical utility of curcumin (CRM) is limited due to its poor oral bioavailability. Lipid based oral formulations (LBOFs) are emerging as useful oral drug delivery systems for 'difficult to deliver' molecules like CRM. In present study, we report novel
Jing Zhao et al.
Biomaterials, 34(13), 3411-3421 (2013-02-05)
We developed a drug delivery system of herceptin-conjugated micelles, which consist of vitamin E TPGS and TPGS-siRNA conjugates, for targeted co-delivery of docetaxel and polo-like kinase 1 siRNA to achieve synergistic effects between the anticancer drug and the small interfering
Benjamin L Shneider et al.
Pediatrics, 130(3), e607-e614 (2012-08-15)
Cholestasis predisposes to fat-soluble vitamin (FSV) deficiencies. A liquid multiple FSV preparation made with tocopheryl polyethylene glycol-1000 succinate (TPGS) is frequently used in infants with biliary atresia (BA) because of ease of administration and presumed efficacy. In this prospective multicenter
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

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