γ-CEHC

Cayman Chemical Item Number 89630

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

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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
  • 2,7,8-trimethyl-2-(β-Carboxy-Ethyl)-6-Hydroxychroman
  • GTM
  • γ-Tocopherol Metabolite
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%
λmax 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
InCHI Code
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​1S/C15H20O4/c1-9-10(2)​14-11(8-12(9)​16)​4-6-15(3,19-14)​7-5-13(17)​18/h8,16H,4-7H2,1-3H3,(H,17,18)​
InCHI Key
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VMJQLPNCUPGMNQ-UHFFFAOYSA-N

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Size Price Quantity Subtotal
1 mg $17.00 $0.00
5 mg $77.00 $0.00
10 mg $136.00 $0.00
25 mg $298.00 $0.00
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Cart Total $0.00

Pricing updated 2015-07-30. 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-CEHC
(±)-α-CMBHC
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