γ-CEHC • γ-Tocopherol Metabolite; GTM; 2,7,8-trimethyl-2-(β-Carboxy-Ethyl)-6-Hydroxychroman (CAS 178167-75-4) || Cayman Chemical

γ-CEHC Exclusive

Cayman Chemical Item Number 89630

γ-Tocopherol Metabolite; GTM; 2,7,8-trimethyl-2-(β-Carboxy-Ethyl)-6-Hydroxychroman (CAS 178167-75-4)

γ-CEHC (CAS 178167-75-4)

Description

The major tocopherol obtained from natural dietary sources is γ-tocopherol, whereas α-tocopherol is the form of Vitamin E typically obtained from synthetic supplements. γ-CEHC is a β-oxidized metabolite of dietary γ-tocopherol that functions as a natriuretic hormone.¹ It was initially purified and characterized from the urine of uremic patients, but it has since been found in urine from both control patients and those with congestive heart failure.² γ-CEHC is also anti-inflammatory, reducing 8-isoprostane and inflammatory eicosanoid synthesis in rat models.³

1 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).

2 Wechter, W.J., Kantoci, D., Murray, E.D., et al. A new endogenous natriuretic factor: LLU-α. Proc Natl Acad Sci USA 93 6002-6007 (1996).

3 Jiang, Q., Elson-Schwab, I., Courtemanche, C., et al. γ-Tocopherol and its major metabolite, in contrast to a-tocopherol, inhibit cyclooxygenase activity in macrophages and epithelial cells. Proc Natl Acad Sci USA 97 11494-11499 (2000).

Synonyms

γ-Tocopherol Metabolite
GTM
2,7,8-trimethyl-2-(β-Carboxy-Ethyl)-6-Hydroxychroman

Formal Name

3,4-dihydro-6-hydroxy-2,7,8-trimethyl-2H-1-benzopyran-2-propanoic acid

CAS Number

178167-75-4

Molecular Formula

C₁₅H₂₀O₄

Formula Weight

264.3

Formulation

A crystalline solid

Purity

>98%

λ_max

296 nm

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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OC(=O)CCC1(C)CCc2cc(O)c(C)c(C)c2O1

Background Reading

Wechter, W.J., Kantoci, D., Murray, E.D., et al. A new endogenous natriuretic factor: LLU-α. Proc Natl Acad Sci USA 93 6002-6007 (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).

Size

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