Bishydroxyphenylbutane - CAS 77-40-7
Catalog number: 77-40-7
Category: Main Product
Molecular Formula:
C16H18O2
Molecular Weight:
242.32
COA:
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Purity:
99%
Appearance:
odorless slightly brown solid
Synonyms:
4,4'-(1-methylpropylidene)bisphenol; 2,2-BIS(P-HYDROXYPHENYL)BUTANE; 2,2-BIS(4-HYDROXYPHENYL)BUTANE; BISPHENOL B; BISHYDROXYPHENYLBUTANE; P,P'-SEC-BUTYLIDENEDIPHENOL; p,p'-Dihydroxy-2,2-diphenylbutane; 4,4'-(1-Methylpropylidene)diphenol
Storage:
Store in a cool, dry place. Store in a tightly closed container.
MSDS:
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Quantity:
Data not available, please inquire.
Boiling Point:
412.2ºC at 760 mmHg
Melting Point:
126ºC
Density:
1.121 g/cm3
1.Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 3. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of 2,2'-disubstituted butestrols and 6,6'-disubstituted metabutestrols.
Hartmann RW, Heindl A, Schwarz W, Schönenberger H. J Med Chem. 1984 Jul;27(7):819-24.
The synthesis of symmetrically 2,2'-disubstituted butestrols [meso-2,3-bis(4-hydroxyphenyl)butanes] and of 6,6'-disubstituted metabutestrols [meso-2,3-bis(3-hydroxyphenyl)butanes] are described [2,2'-substituents: H (1), OH (2), F (3), Cl (4), Br (5), CH3 (6), and C2H5 (7); 6,6'-substituents: H (8), OH (9), Cl (10), and CH3 (11)]. Compounds 1-11 were obtained by reductive coupling of the corresponding 1-phenylethanols with TiCl3/LiAlH4 and separation of the meso diastereomers. The binding affinity of the test compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. With the exception of 9, all other compounds showed remarkably high relative binding affinity (RBA) values between 1.0 and 29% that of estradiol. Compounds 3 and 6 (RBA values: 15 and 29), as well as 10 and 11 (1.7 and 5.2), exceeded those of the corresponding unsubstituted compounds 1 and 8 (12 and 1.0). The compounds exhibited strong (3, 4, 6, and 7), moderate (1, 2, and 10), weak (11), or no (8) estrogenic activity in the uterine weight test of the immature mouse.
2.Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
Hartmann RW, Heindl A, Schneider MR, Schönenberger H. J Med Chem. 1986 Mar;29(3):322-8.
trans-1,2-Bis(trifluoromethyl)-1,2-bis(4- and 3-hydroxyphenyl)ethenes 2 and 4 were prepared by reductive coupling (TiCl4/Zn/pyridine) of the methoxy-substituted alpha, alpha, alpha-trifluoroacetophenones, separation of the resulting cis- and trans-stilbene derivatives, and ether cleavage with BBr3. The cis-stilbenes were catalytically hydrogenated to give meso-1,1,1,4,4,4-hexafluoro-2,3-bis(4- and 3-hydroxyphenyl)butanes 6 and 8. Compounds 2, 4, 6, and 8 showed 2- to 10-fold increased binding affinities for the estradiol receptor (E2R) and enhanced estrogenicity in the uterine weight test of the immature mouse compared to their unfluorinated analogues. Compound 8 exhibited a 46% inhibition of the estrone-stimulated uterine growth. Antitumor activity was evaluated with use of the transplantable, hormone-dependent MXT mammary tumor of the BD2F1 mouse. All compounds showed tumor growth inhibitory activity corresponding to their RBA values. The most interesting compound 8 led to a significant inhibition of the tumor growth on the DMBA-induced hormone-dependent mammary carcinoma of the Sprague-Dawley rat.
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CAS 77-40-7 Bishydroxyphenylbutane

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