| References |
| 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 |
Wet ice
in continental US; may vary elsewhere
|
| SMILES |
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 |
Global Purchasing |
| 1 mg |
|
| 5 mg |
|
| 10 mg |
|
| 25 mg |
|
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).
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