5273-86-9

Usage

Uses

Used in Pharmaceutical Industry:
BETA-ASARONE is used as a reference standard for the analysis of herbal medicinal products, ensuring the quality and efficacy of these products.
Used in Chemical Synthesis:
BETA-ASARONE is used as a key intermediate in the preparation of various compounds, such as 2,4,5-trimethoxycinnamaldehyde and 2,4,5-trimethoxycinnamyltosylhydrazone, as well as 1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane.
Used in Agriculture:
In the agricultural industry, BETA-ASARONE is utilized as a grain fumigant and an insect chemosterilant, helping to protect crops from pests and improve yield.
Used in Research:
Due to its unique chemical properties and antibiotic nature, BETA-ASARONE is also used in research for further exploration of its potential applications and effects on various biological systems.

Safety Profile

Questionable carcinogen withexperimental carcinogenic data reported. Human mutationdata reported. When heated to decomposition it emitsacrid smoke and irritating vapors.

InChI:InChI=1/C18H24O3/c1-7-16(19-4)13-10-11-14(17(8-2)20-5)15(12-13)18(9-3)21-6/h7-12H,1-6H3

Upstream product

• 67-56-1 methanol 
• 2883-98-9 α-asarone 
• 86543-61-5 (2S,3S)-3-Hydroxy-2-(2,4,5-trimethoxy-phenyl)-butyric acid 
• 5353-15-1 1-allyl-2,4,5-trimethoxybenzene 
• 29652-82-2 1-(2,4,5-Trimethoxyphenyl)propan-1-ol 
• 4460-86-0 asaraldehyde 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 137-40-6 sodium proprionate 
• 123-62-6 propionic acid anhydride 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 

Downstream Products

• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 2883-98-9 α-asarone 
• 19785-02-5 (E)-1,4-dimethoxy-2-(prop-1-enyl)benzene 
• 4460-86-0 asaraldehyde 
• 73036-51-8 andamanicin 
• 99217-07-9 (Z)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde 
• 99217-07-9 trans 2,4,5-trimethoxy cinnamaldehyde 
• 14227-14-6 1,2,4-trimethoxy-5-nitrobenzene 
• 1214-72-8 1-(1,2-dibromo-propyl)-2,4,5-trimethoxy-benzene 
• 106128-88-5 2,4,5-trimethoxy cinnamaldehyde 
• 264147-43-5 methyl 3-(2,4,5-trimethoxyphenyl)propanoate 
• 352279-44-8 methyl 2,4,5-trimethoxycinnamate 
• 1192002-97-3 2,3-dihydro-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-1-(3-(2,4,5-trimethoxyphenyl)pentan-2-yl)-2-methyl-1H-indene 
• 4640-41-9 2,3-dichloro-5,6-dicyanohydroquinone 

Relevant academic research and scientific papers

Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins

An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.

Cobalt-Catalyzed Z to e Isomerization of Alkenes: An Approach to (E)-β-Substituted Styrenes

An efficient cobalt-catalyzed Z to E isomerization of β-substituted styrenes using the amido-diphosphine ligand was developed, delivering the (E)-isomers with good functional tolerance and high stereoselectivity. The reaction could be scaled up to gram-scale with a catalyst loading of 0.1 mol %, using a mixture of (Z)- and (E)-alkene as the starting material. Preliminary mechanistic studies indicated that cobalt(I)-hydride and a benzylic-cobalt species were probably involved in the reaction, as supported by experiments and DFT calculations.

Larvicidal and structure-activity studies of natural phenylpropanoids and their semisynthetic derivatives against the tobacco armyworm Spodoptera litura (Fab.) (Lepidoptera: Noctuidae)

The larvicidal activity of 18 phenylpropanoids, 1-18, including phenylpropenoate, phenylpropenal, phenylpropene, and their semisynthetic analogues, were evaluated against the tobacco armyworm, Spodoptera litura (FAB.), to identify promising structures with insecticidal activity. Amongst various phenylpropanoids, isosafrole, a phenylpropene, showed the best activity, with an LC50 value of 0.6 μg/leaf cm2, followed by its hydrogenated derivative dihydrosafrole (LC50=2.7 μg/leaf cm 2). The overall larvicidal activity of various phenylpropene derivatives was observed in the following order: isosafrole (6) >dihydrosafrole (16)>safrole (12)>anethole (4)>methyl eugenol (11)>eugenol (13)>β-asarone (8)>dihydroasarone (18)>dihydroanethole (15). Dihydrosafrole might be a promising compound, although presenting a lower larvicidal activity than isosafrole, because of its better stability and resistance to oxidative degradation (due to the removal of the extremely reactive olefinic bond) in comparison to isosafrole. Such structure-activity relationship studies promote the identification of lead structures from natural sources for the development of larvicidal products against S. litura and related insect pests.

Role of the methoxy group in product formation via TiCl 4 promoted 4-phenyldioxolane isomerizations

The product distribution obtained from the TiCl 4 initiated intramolecular isomerizations of 4-methoxyphenyl-and trimethoxyphenyldioxolanes at -78 °C, -30 °C and 0 °C provided insights into the important regiochemical role played by these groups in such Mukaiyama-type rearrangements through their resonance effects on the aryl ring of the dioxolanes. ARKAT USA, Inc.

An effective system to synthesize hypolipidemic active α-asarone and related methoxylated (E)-arylalkenes

Methoxylated (E)-arylalkenes (1a-1k) were prepared in two steps by an improved Grignard reaction comprising the reverse addition of alkylmagnesium bromide to benzaldehydes (2a-2k) in anhydrous ether and toluene into arylalkanols (3a-3k) in high yield, followed by dehydration with silica gel under microwave irradiation for 3-12 min, depending upon the substituents attached to the aromatic ring to afford hypolipidemic active α-asarone (1a) and related methoxylated (E)-arylalkenes (1b-1k).

A PROCESS FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE ALPHA-ASARONE FROM TOXIC BETA-ASARONE RICH ACORUS CALAMUS OIL

The present invention relates to a process for the preparation of high purity and yield α-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from β-asarone or β-asarone rich Acorus calamus oil containing α and γ-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and α-asarone can also be obtained by treating the hydrogenated product of β-asarone or β-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.