(±)-α-CMBHC

Cayman Chemical Item Number 10008652

(CAS 7083-09-2)

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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 HepG2 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%
λmax 210, 292 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC1=C(C)​C(O)​=C(C)​C2=C1OC(CCCC(C)​C(O)​=O)​(C)​CC2
InCHI Code
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​1S/C19H28O4/c1-11(18(21)​22)​7-6-9-19(5)​10-8-15-14(4)​16(20)​12(2)​13(3)​17(15)​23-19/h11,20H,6-10H2,1-5H3,(H,21,22)​
InCHI Key
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QWPNLVBAEZJBMI-UHFFFAOYSA-N

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

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
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Related Products

α-CEHC
α-Tocotrienol
γ-CEHC
γ-Tocotrienol
δ-CEHC
δ-Tocotrienol
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