(E/Z)-4-hydroxy Tamoxifen (CAS 68392-35-8) | Cayman Chemical
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(E/Z)-4-hydroxy Tamoxifen

Item № 17308
CAS № 68392-35-8
Purity ≥98% (E) and (Z) isomers (50:50)
product image
                (CAS 68392-35-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $29.00 0.00
     10 mg $55.00 0.00
     25 mg $123.00 0.00
     50 mg $218.00 0.00

Pricing updated 2018-12-10. Prices are subject to change without notice.

Description
Synonyms
  • Afimoxifene
  • 4-OHT
  • 4-hydroxy Tamoxifen

Tamoxifen (Item No. 13258) is a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. Although it is an antagonist of ER action in breast tissue, it acts as an ER agonist in bone and blood vessels and a partial ER agonist in uterine tissues. (E/Z)-4-hydroxy Tamoxifen is an active metabolite of tamoxifen that is formed by the action of cytochrome P450 2D6 in human liver.1 It exhibits more potent estrogen agonist/antagonist activity than its parent compound and can inhibit MCF-7 and MDA-MB-231 cell proliferation with IC50 values of 27 and 18 µM, respectively.2 (E/Z)-4-hydroxy Tamoxifen has been used to stimulate LC3 lipidation and formation of autophagic vesicles in a superoxide-dependent manner.3

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Technical Information
Formal Name
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
CAS Number
68392-35-8
Synonyms
  • Afimoxifene
  • 4-OHT
  • 4-hydroxy Tamoxifen
Molecular Formula
C26H29NO2
Formula Weight
387.5
Purity
≥98% (E) and (Z) isomers (50:50)
Formulation
A crystalline solid
λmax
205, 246, 287 nm
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=C(O)C=C2)/C3=CC=C(OCCN(C)C)C=C3
InChI Code
InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
InChI Key
TXUZVZSFRXZGTL-QPLCGJKRSA-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
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Desta, Z., Ward, B.A., Soukhova, N.V., et al. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6 Journal of Pharmacology and Experimental Therapeutics 310(3), 1062-1075 (2004).

2. Seeger, H., Huober, J., Wallwiener, D., et al. Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen Hormone and Metabolic Research 36(5), 277-280 (2004).

3. Duan, L., Danzer, B., Levenson, V.V., et al. Critical roles for nitric oxide and ERK in the completion of prosurvival autophagy in 4OHTAM-treated estrogen receptor-positive breast cancer cells Cancer Letters 353(2), 290-300 (2014).

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