56438-59-6

Usage

Also known as

estragole epoxide

Physical state

clear, colorless liquid

Functional group

epoxide

Chemical structure

three-membered ring of one oxygen and two carbon atoms

Uses

commonly used in the production of fragrances and flavorings

Odor

sweet, licorice-like scent

Health effects

potential carcinogenic effects

Regulation

banned as a food additive in many countries

Natural occurrence

found in some herbs and spices

Precautions

limit exposure to high doses of 2-[2-(4-methoxyphenyl)ethyl]oxirane

InChI:InChI=1/C11H14O2/c1-12-10-5-2-9(3-6-10)4-7-11-8-13-11/h2-3,5-6,11H,4,7-8H2,1H3

Upstream product

• 20401-88-1 3-(4-methoxyphenyl)propional 
• 2181-42-2 trimethylsulphonium iodide 
• 59363-12-1 1-chloro-4-(4-methoxyphenyl)-2-butanol 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 20574-98-5 4-(p-methoxyphenyl)but-1-ene 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 31179-52-9 p-anisylmagnesium bromide 

Downstream Products

• 59363-22-3 4-(4-methoxyphenyl)butane-1,2-diol 
• 1089731-11-2 1-(4-methoxyphenyl)oct-7-en-3-ol 
• 1451998-94-9 (2R,6S)-2-(3,4-dimethoxyphenyl)-6-(4-methoxyphenethyl)tetrahydro-2H-pyran 
• 56438-65-4 Acetic acid 5-(4-methoxy-phenyl)-1-[2-(4-methoxy-phenyl)-ethyl]-3-oxo-pentyl ester 
• 56438-61-0 1,7-bis(4-methoxyphenyl)-5-hydroxyhept-3-one 
• 79422-46-1 1,7-bis(4-methoxyphenyl)-4-hepten-3-one 
• 79422-48-3 1,7-bis(3-iodo-4-methoxyphenyl)-4-hepten-3-one 
• 89789-90-2 2-Hydroxy-5-{2-[2-hydroxy-4-(4-methoxy-phenyl)-butylamino]-ethoxy}-benzamide 
• 344249-67-8 4-(4-Methoxy-phenyl)-1-{2-[2-(4-methoxy-phenyl)-ethyl]-[1,3]dithian-2-yl}-butan-2-ol 

Relevant academic research and scientific papers

Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues

A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.

Convenient access to bicyclic and tricyclic diazenes

(Chemical Equation Presented) Heating the tosylhydrazone of an ω-alkenyl ketone or aldehyde to reflux in toluene in the presence of K2CO3 delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. Th

Alpha-(phenylalkyl) pyridinealkanol derivatives

This invention relates to novel α-(phenylalkyl) pyridinealkanol derivatives useful in the treatment of diseases or disorders mediated by platelet-activating factor. This invention further relates to pharmaceutical compositions of such α-(phenylalkyl)pyridinealkanol derivatives.

β-Adrenergic blocking agents: Substituted phenylalkanolamines. Effect of side-chain length on β-blocking potency in vitro

The synthesis of a group of potential β-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for β-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the β-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)(n)CHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of β-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent β-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.

Reaction of Aryl and Vinyl Halides with Zerovalent Nickel-Preparative Aspects and the Synthesis of Alnusone

Zerovalent nickel complexes such as bis(1,5-cyclooctadiene)nickel and tetrakis(triphenylphosphine)nickel react rapidly with aryl and vinyl halides to produce the symmetrical coupling products, a low-temperature analogue of the Ullman reaction.The reaction proceeds through oxidative addition of the organic halide to Ni(0), and the reactivity of the Ni(II)intermediates has been examined.Arylnickel halide complexes decompose rapidly to biaryls in DMF.The coupling of simple vinyl halides proceeds with isomerization of the double bond but 3-haloacrylates give efficient co upling with retention of geometry.Cyclizations to form ortho-bridged biaryls are efficient in simple cases (6-, 7-, 8-, 9-, 10-, and 14-membered rings) but fail with an ortho-disubstituted case.The 13-membered meta-bridged cyclic biphenyl, alnusone, is prepared efficiently with the crucial aryl halide coupling to form the ring proceeding in 50percent yield.A side reaction promoted by the presence of protons and with certain ortho-substituted aryl halides is reduction of the aryl halide to the arene.This process can be enhanced by deliberate addition of acid during reaction with Ni(0) and a series of aryl halides underwent succesful reduction.