(±)-α-CMBHC
Item № 10008652
CAS № 7083-09-2
Purity ≥98%
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
1 mg $31.00 $0.00
5 mg $140.00 $0.00
10 mg $248.00 $0.00
25 mg $543.00 $0.00

Pricing updated 2016-05-06. Prices are subject to change without notice.

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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

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Technical Information
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
Purity ≥98%
Formulation A crystalline solid
λmax 210, 292 nm
SMILES CC1=C(C)C(O)=C(C)C2=C1OC(CCCC(C)C(O)=O)(C)CC2
InChI Code 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 QWPNLVBAEZJBMI-UHFFFAOYSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
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Additional Information

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References & Background Reading
Product Description References

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 .alpha.-CEHC in human urine: Studies using deuterated .alpha.-tocopheryl acetates. FEBS Lett 437 145-148 (1998).

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

5. Sontag, T.J., and Parker, R.S. Cytochrome P450 .omega.-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 .omega.-oxidation and consecutive .beta.-oxidation. Free Radic Biol Med 31(2) 226-232 (2001).

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