A biologically active form of vitamin E
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(+)-δ-Tocopherol

Item No. 31589

Technical Information
Formal Name
(2R)-3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
CAS Number
119-13-1
Synonyms
  • D-δ-Tocopherol
Molecular Formula
C27H46O2
Formula Weight
Purity
≥98%
A solution in hexane
Chloroform: SolubleEthanol: SolubleHexane: SolubleMethanol: Soluble
SMILES
CC1=C2C(CC[C@@](C)(O2)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C)=CC(O)=C1
InChi Code
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m0/s1
InChi Key
GZIFEOYASATJEH-BERHBOFZSA-N
Origin
Plant/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    (+)-δ-Tocopherol is a biologically active form of vitamin E, a lipid-soluble antioxidant that protects cellular membranes from oxidative damage.1,2 It reduces cumene hydroperoxide-induced lipid peroxidation in hepatocytes when used at a concentration of 20 µM but induces lipid peroxidation in hepatic microsomes at 100 µM.3 (+)-δ-Tocopherol (40 µM) decreases capillary formation of HMEC-1 blood endothelial cells.4 It also decreases the expression of VCAM in, and the invasiveness of, HMEC-1 cells. (+)-δ-Tocopherol (10 µM) reduces estrogen-induced increases in the expression of the estrogen-responsive genes encoding TFF/pS2, cathepsin D, PGR, CITED1, and SERPINA1 and the levels of 8-hydroxy-2’-deoxyguanosine (8-oxo-dG) and nitrotyrosine in MCF-7 breast cancer cells.5 Dietary administration of (+)-δ-tocopherol (0.2%) reduces tumor growth in an estrogen-supplemented MCF-7 mouse xenograft model. [Matreya, LLC. Catalog No. 1790]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brigelius-Flohé, R., and Traber, M.G. Vitamin E: Function and metabolism. The FASEB Journal 13(10), 1145-1155 (1999).

    2. van Acker, F.A., Schouten, O., Haenen, G.R., et alFlavonoids can replace α-tocopherol as an antioxidant. FEBS Lett. 473(2), 145-148 (2000).

    3. Tafazoli, S., Wright, J.S., and O'Brien, P.J. Prooxidant and antioxidant activity of vitamin E analogues and troglitazone. Chem. Res. Toxicol. 18(10), 1567-1574 (2005).

    4. Wells, S.R., Jennings, M.H., Rome, C., et alα-, γ- and δ-tocopherols reduce inflammatory angiogenesis in human microvascular endothelial cells. J. Nutr. Biochem. 21(7), 589-597 (2010).

    5. Bak, M.J., Gupta, S.D., Wahler, J., et alInhibitory effects of γ- and δ-tocopherols on estrogen-stimulated breast cancer in vitro and in vivo. Cancer Prev. Res. (Phila.) 10(3), 188-197 (2017).