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Cat. Number
080172706948095
Chemical Name
δ-CEHC
References
Formal Name 3,​4-​dihydro-​6-​hydroxy-​2,​8-​dimethyl-​2H-​1-​benzopyran-​2-​propanoic acid
CAS Number 1221504-67-1
Molecular Formula C14H18O4
Formula Weight 250.3
Formulation A crystalline solid
Purity >95%
λmax 205, 298 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES OC(=O)​CC[C@]​1(C)​CCc2cc(O)​cc(C)​c2O1

Background Reading

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

Christen, S., Woodall, A.A., Shigenaga, M.K., et al. γ-Tocopherol traps mutagenic electrophiles such as NOx and complements a-tocopherol: Physiological implications. Proc Natl Acad Sci USA 94 3217-3222 (1997).

Chiku, S., Hamamura, K., and Nakamura, T. Novel urinary metabolite of d-δ-tocopherol in rats. J Lipid Res 25 40-48 (1984).

Weiser, H., Riss, G., and Kormann, A.F. Biodiscrimination of the eight α-tocopherol stereoisomers results in preferential accumulation of the four 2R forms in tissues and plasma of rats. J Nutr 126(10) 2539-2549 (1996).

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Description

Molecules having vitamin E antioxidant activity include four tocopherols (α, β, γ, δ) and four tocotrienols (α, β, γ, δ).1 One form, α-tocopherol has the highest biological activity based on fetal resorption assays.2 δ-CEHC is a major β-oxidation metabolite of δ-tocopherol.3,4 Approximately 50% of a 3H-δ-tocopherol given as an intraperitoneal dose in rat is recovered in the urine as δ-CEHC, indicating this is the major route of metabolism.4

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

2 Weiser, H., Riss, G., and Kormann, A.F. Biodiscrimination of the eight α-tocopherol stereoisomers results in preferential accumulation of the four 2R forms in tissues and plasma of rats. J Nutr 126(10) 2539-2549 (1996).

3 Christen, S., Woodall, A.A., Shigenaga, M.K., et al. γ-Tocopherol traps mutagenic electrophiles such as NOx and complements a-tocopherol: Physiological implications. Proc Natl Acad Sci USA 94 3217-3222 (1997).

4 Chiku, S., Hamamura, K., and Nakamura, T. Novel urinary metabolite of d-δ-tocopherol in rats. J Lipid Res 25 40-48 (1984).

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