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(±)-α-CMBHC

Cayman Chemical Item Number 10008652

(CAS 7083-09-2)

(±)-α-CMBHC (CAS 7083-09-2)

See more	Antioxidants (62) Inflammation (383) Oxidative Injury (258)

Description

Vitamin E is a well known antioxidant that exists in eight natural forms: four tocopherols (α, β, δ, and γ) and four tocotrienols (α, β, δ, and γ). α-Tocopherol is the major lipid soluble antioxidant in vivo and protects against lipid peroxidation.^1,2 α-CEHC is the major urinary metabolite of α-tocopherol following vitamin E supplementation.³ α-CMBHC is the longer side-chain precursor of α-CEHC and a minor metabolite of α-tocopherol.^4,5 Hep-G₂ cells release α-CEHC, α-CMBHC, and α-CMHHC into the medium when treated with all rac α-tocopherol. Pretreatment of Hep-G₂ cells with rifampicin, an inducer of the CYP3A family of cytochrome P450s, results in a 5-fold increase in α-CEHC. This indicates that metabolism of α-tocopherol proceeds by initial ω-oxidation to precursors of α-CMBHC followed by β-oxidation to shorter chain metabolites such as α-CEHC.⁶

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

2 Brigelius-Flohé, R., and Traber, M.G. Vitamin E: Function and metabolism. FASEB J 13 1145-1155 (1999).

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 Pope, S.A.S., Burtin, G.E., Clayton, P.T., et al. New synthesis of (±)-α-CMBHC and its confirmation as a metabolite of α-Tocopherol (vitamin E). Bioorg Med Chem 9 1337-1343 (2001).

5 Sontag, T.J., and Parker, R.S. Cytochrome P450 ω-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem 277(28) 25290-25296 (2002).

6 Birringer, M., Drogan, D., and Brigelius-Flohé, R. Tocopherols are metabolized in HepG2 cells by side chain ω-oxidation and consecutive β-oxidation. Free Radic Biol Med 31(2) 226-232 (2001).

Formal Name	3,4-dihydro-6-hydroxy-α,2,5,7,8-pentamethyl-2H-1-benzopyran-2-pentanoic acid
CAS Number	7083-09-2
Molecular Formula	C₁₉H₂₈O₄
Formula Weight	320.4
Formulation	A crystalline solid
Purity	≥98%
λ_max	210, 292 nm
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CC1=C(C)C(O)=C(C)C2=C1OC(CCCC(C)C(O)=O)(C)CC2

Background Reading

Sontag, T.J., and Parker, R.S. Cytochrome P450 ω-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem 277(28) 25290-25296 (2002).

Pope, S.A.S., Burtin, G.E., Clayton, P.T., et al. New synthesis of (±)-α-CMBHC and its confirmation as a metabolite of α-Tocopherol (vitamin E). Bioorg Med Chem 9 1337-1343 (2001).

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).

Birringer, M., Drogan, D., and Brigelius-Flohé, R. Tocopherols are metabolized in HepG2 cells by side chain ω-oxidation and consecutive β-oxidation. Free Radic Biol Med 31(2) 226-232 (2001).

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

Brigelius-Flohé, R., and Traber, M.G. Vitamin E: Function and metabolism. FASEB J 13 1145-1155 (1999).

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(±)-α-CMBHC is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size	Price	Quantity	Subtotal
1 mg	$31.00		$0.00
5 mg	$140.00		$0.00
10 mg	$248.00		$0.00
25 mg	$543.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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