89106-42-3

Basic information

• Product Name: Benzenemethanol, a-ethyl-2,5-dimethoxy-
• CAS NO: 89106-42-3
• Molecular Formula: C11H16O3
• Molecular Weight: 196.246
• Mol File: 89106-42-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-ethyl-2,5-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-ethyl-2,5-dimethoxy-(89106-42-3)
• EPA Substance Registry System: Benzenemethanol, a-ethyl-2,5-dimethoxy-(89106-42-3)

Safety Data

• Hazardous Substances Data: 89106-42-3(Hazardous Substances Data)

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 89106-40-1 C₁₈H₂₂O₄ 
• 124711-23-5 (E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)-2-methylprop-2-en-1-one 
• 5803-30-5 2',5'-dimethoxypropiophenone 
• 89106-41-2 C₂₂H₃₀O₄ 

Relevant articles and documents

Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols

The synthesis of symmetrically 4,4'-, 5,5'-, and 6,6'-disubstituted derivatives of the mammary tumor inhibiting antiestrogen metahexestrol [meso-3,4-bis(3-hydroxyphenyl)hexane] (1) are described [4,4'-disubstituents: F(2), Cl (3), Br (4), I (5), CH2N(CH3)2 (6), CH3 (7), CH2OCH3 (8), CH2OC2H5 (9), CH2OH (10), NO2 (11), NH2 (12), N(CH3)2 (13), COCH3 (14), and C2H5 (15); 5,5'-substituents: OH (16) and Cl (17); 6,6'-disubstituents: OH (18), F (19), Cl (20), and CH3 (21)]. The synthesis of 1-3, 16, and 19 was accomplished by reductive coupling of the propiophenones with TiCl4/Zn and subsequent hydrogenation of the cis-3,4-diphenylhex-3-enes. Compounds 17, 18, 20, and 21 were synthesized by coupling the 1-phenyl-1-propanols with TiCl3/LiAlH4 and separation of the meso diastereomers, while 4-15 were obtained by substitution of metahexestrol. The binding affinity of these compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. The test compounds showed relative binding affinity (RBA) values between 15 and 0.5% were evaluated in the mouse uterine weight test. They showed a similar (2 and 12), slightly increased (19 and 21), or strongly enhanced (7 and 20) estrogenicity compared to that of metahexestrol. Compounds 1, 2, 7, 12, and 21 exhibited antiestrogenic activity inhibiting the estrone-stimulated uterine growth (24 to 60% inhibition).