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α-CEHC

Cayman Chemical Item Number 10007705

α-CEHC

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Description

Molecules having vitamin E antioxidant activity include four tocopherols (α, β, δ, and γ) and four tocotrienols ((α, β, δ, and γ).1 α-Tocopherol is the major lipid soluble antioxidant in vivo and protects against lipid peroxidation.2 α-CEHC is the major urinary metabolite of α-tocopherol following vitamin E supplementation.3 The concentration of α-CEHC in human serum is in the range of 5-10 pmol/ml but increases significantly up to 200 pmol/ml upon supplementation with RRR-α-tocopherol. About one-third of the α-CEHC circulating in the blood is present as a glucuronide conjugate.4 α-CEHC was only excreted when a threshold concentration of 7-9 µmol α-tocopherol/g total lipid in plasma was exceeded. Therefore, excretion of α-CEHC may be considered to be a marker of optimum vitamin E intake.5

1 Kamal-Eldin, A., and Appelqvist, L. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31 671-701 (1996).

2 Burton, G.W., Joyce, A., and Ingold, K.U. Is vitamin E the only lipid-soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membranes? Arch Biochem Biophys 221(1) 281-290 (1983).

3 Traber, M.G., Elsner, A., and Brigelius-Flohé, R. Synthetic as compared with natural vitamin E is preferentially excreted as α-CEHC in human urine: Studies using deuterated α-tocopheryl acetates. FEBS Lett 437 145-148 (1998).

4 Stahl, W.S., Graf, P., Brigelius-Flohé, R., et al. Quantification of the α- and γ-tocopherol metabolites 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman and 2,7,8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman in human serum. Anal Biochem 275 254-259 (1999).

5 Schultz, M., Leist, M., Petrzika, M., et al. Novel urinary metabolite of α-tocopherol, 2,5,7,8-tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman, as an indicator of an adequate vitamin E supply. Am J Clin Nutr 62(6) 1527S-34S (1995).

Formal Name 3,​4-​dihydro-​6-​hydroxy-​2,​5,​7,​8-​tetramethyl-​2H-​1-​benzopyran-​2-​propanoic acid
Molecular Formula C16H22O4
Formula Weight 278.3
Formulation A crystalline solid
Purity ≥98%
λmax 206, 291 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC(=O)​CC[C@]​1(C)​CCc2c(O1)​c(C)​c(C)​c(O)​c2C

Background Reading

Traber, M.G., Elsner, A., and Brigelius-Flohé, R. Synthetic as compared with natural vitamin E is preferentially excreted as α-CEHC in human urine: Studies using deuterated α-tocopheryl acetates. FEBS Lett 437 145-148 (1998).

Schultz, M., Leist, M., Petrzika, M., et al. Novel urinary metabolite of α-tocopherol, 2,5,7,8-tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman, as an indicator of an adequate vitamin E supply. Am J Clin Nutr 62(6) 1527S-34S (1995).

Stahl, W.S., Graf, P., Brigelius-Flohé, R., et al. Quantification of the α- and γ-tocopherol metabolites 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman and 2,7,8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman in human serum. Anal Biochem 275 254-259 (1999).

Burton, G.W., Joyce, A., and Ingold, K.U. Is vitamin E the only lipid-soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membranes? Arch Biochem Biophys 221(1) 281-290 (1983).

Kamal-Eldin, A., and Appelqvist, L. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31 671-701 (1996).

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Size Price Quantity Subtotal
1 mg $21.00 $0.00
5 mg $95.00 $0.00
10 mg $168.00 $0.00
25 mg $368.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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(±)-α-CMBHC
α-Tocotrienol
γ-CEHC Exclusive
γ-Tocotrienol
δ-CEHC
δ-Tocotrienol
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