An oxidative metabolite of vitamin E
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D-α-Tocopheryl Quinone

Item No. 35365

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione
CAS Number
7559-04-8
Synonyms
  • α-Tocopherylquinone
  • α-Tocoquinone
  • α-TQ
  • Tocopherol Quinone
Molecular Formula
C29H50O3
Formula Weight
446.7
Purity
≥98%
Formulation (Request formulation change)
A 100 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 10 mg/mlEthanol: 16 mg/ml
λmax
268 nm
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C(C(C)=C(C1=O)C)=O)C
InChi Code
InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
InChi Key
LTVDFSLWFKLJDQ-IEOSBIPESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $32

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    50 mg

    $148

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    100 mg

    $203

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    250 mg

    $465

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    D-α-Tocopheryl quinone is an active oxidative metabolite of vitamin E and an essential cofactor for mitochondrial fatty acid desaturases.1 It has antioxidant activity in oxygen radical absorbance capacity (ORAC) and radical trapping assays when used at a concentration of 25 µM and inhibits ferroptosis induced by (1S,3R)-RSL3 (Item No. 19288) in Q7 cells (EC50 = 0.233 µM).2 D-α-Tocopheryl quinone (20 mg/kg) decreases serum malondialdehyde (MDA) and blood glucose levels and restores the number and diversity of intestinal microflora in a rat model of high cholesterol and cholate diet-induced non-alcoholic steatohepatitis (NASH).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Infante, J.P. A function for the vitamin E metabolite alpha-tocopherol quinone as an essential enzyme cofactor for the mitochondrial fatty acid desaturases. FEBS Lett. 446(1), 1-5 (1999).

    2. Hinman, A., Holst, C.R., Latham, J.C., et al. Vitamin E hydroquinone is an endogenous regulator of ferroptosis via redox control of 15-lipoxygenase. PLoS One 13(8), e0201369 (2018).

    3. Sun, T., Zhang, B., Ru, Q.-J., et al. Tocopheryl quinone improves non-alcoholic steatohepatitis (NASH) associated dysmetabolism of glucose and lipids by upregulating the expression of glucagon-like peptide 1 (GLP-1) via restoring the balance of intestinal flora in rats. Pharm. Biol. 59(1), 723-731 (2021).