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Join us! · ENDO 2015 · San Diego, California · March 5-8, 2015 · Booth 1935
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Cayman is a manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research. Analytical testing services and custom synthesis are also available.

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2015 Cayman Chemical Company


Cayman Chemical Item Number 10008652

(CAS 7083-09-2)

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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
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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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Cart Total $0.00

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Pricing updated 2015-03-02. Prices are subject to change without notice.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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