3391-75-1

Basic information

• Product Name: 4-HYDROXY-3-METHOXYSTILBENE
• Synonyms: 4-Stilbenol,3-methoxy- (7CI,8CI); 3-Methoxy-4-hydroxystilbene; 4-Hydroxy-3-methoxystilbene;NSC 126252
• CAS NO: 3391-75-1
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 0
• Mol File: 3391-75-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 366.7°Cat760mmHg
• Flash Point: 196.5°C
• Appearance: /
• Density: 1.159g/cm³
• Vapor Pressure: 6.83E-06mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 4-HYDROXY-3-METHOXYSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHOXYSTILBENE(3391-75-1)
• EPA Substance Registry System: 4-HYDROXY-3-METHOXYSTILBENE(3391-75-1)

Safety Data

• Hazardous Substances Data: 3391-75-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H14O2/c1-17-15-11-13(9-10-14(15)16)8-7-12-5-3-2-4-6-12/h2-11,16H,1H3

Upstream product

• 114-70-5 sodium phenylacetate 
• 121-33-5 vanillin 
• 881-68-5 vanillin acetate 
• 66476-02-6 1-(4-hydroxy-3-methoxyphenyl)-2-phenylethan-1-one 
• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 54208-11-6 α-phenyl-4-acetoxy-3-methoxycinnamic acid 
• 54208-31-0 (Z)-3-(4-Acetoxy-3-methoxy-phenyl)-2-phenyl-acrylic acid methyl ester 
• 4112-89-4 2-methoxyphenyl 2-phenylacetate 
• 3892-92-0 (E)-3,4-dimethoxystilbene 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-42-5 styrene 
• 100-39-0 benzyl bromide 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 

Downstream Products

• 24033-07-6 4-methoxy-N-(4-hydroxy-3-methoxybenzylidene)aniline 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 58285-79-3 2-methoxy-4-(((4-methoxyphenyl)amino)methyl)phenol 
• 112635-82-2 3-(3,4-diacetoxyphenyl)-2,3-dihydro-2-phenyl-6-(2-phenylvinyl)-1,4-benzodioxin 
• 112635-80-0 3-(3,4-hydroxyphenyl)-2,3-dihydro-2-phenyl-6-(2-phenylvinyl)-1,4-dioxin 
• 122917-29-7 2-Methoxy-4-[7-methoxy-2-phenyl-5-((E)-styryl)-2,3-dihydro-benzofuran-3-yl]-phenol 
• 100-52-7 benzaldehyde 
• 121-33-5 vanillin 
• 10366-19-5 4'-hydroxy-3'-methoxy-1,2-diphenylethane 
• 1466-17-7 3,4-dimethoxystilbene 

Relevant articles and documents

Wittig Olefination Using Phosphonium Ion-Pair Reagents Incorporating an Endogenous Base

Despite common perception, the use of strong bases in Wittig chemistry is utterly unnecessary: we report a series of novel ion-pair phosphonium carboxylate reagents which are essentially "storable ylides". These reagents are straightforwardly prepared in excellent yields, and their fluxional nature permits clean olefination of a broad range of aldehydes and even hemiacetals.

Tetrahydropyrrolization of Resveratrol and Other Stilbenes Improves Inhibitory Effects on DNA Oxidation

The inhibitory effect of resveratrol on DNA oxidation caused by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) was found to be enhanced if the C=C bond in resveratrol was converted into tetrahydropyrrole by reaction with azomethine ylide (CH2=N+(CH3)CH2?). This encouraged us to explore whether the inhibitory activities of other stilbenes could also be increased by the same method. We found that the inhibitory effects of the tetrahydropyrrole derivatives on AAPH-induced oxidation of DNA were higher than those of the corresponding stilbenes, because the tetrahydropyrrole motif can provide hydrogen atoms to be abstracted by radicals. Therefore, the tetrahydropyrrolization offered an advantage for enhancing the antioxidant effects of stilbenes. Notably, (CH3)3SiCH2N(CH3)CH2OCH3(in the presence of CF3COOH) and (CH3)3NO (in the presence of LiN(iPr)2) can be used to generate azomethine ylide for the tetrahydropyrrolization of stilbenes containing electron-withdrawing and -donating groups, respectively.

Cu(acac)2-catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents and their olefination reaction with aromatic aldehydes

An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields. Georg Thieme Verlag Stuttgart · New York.