2883-98-9

Basic information

• Product Name: alpha-Asarone
• Synonyms: alpha-Asarion;alpha-Asaron;2,4,5-Trimethoxy-1-propenylbenzene alpha-Asarone trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene trans-1-Propenyl-2,4,5-trimethoxybenzene;ASARONE;ASARONE, A-;(e)-1,2,4-trimethoxy-5-(1-propenyl)benzene;A-ASARONE;ALPHA-ASARONE
• CAS NO: 2883-98-9
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• EINECS: 220-743-6
• Product Categories: API;Aromatic Ethers
• Mol File: 2883-98-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 57-61 °C(lit.)
• Boiling Point: 296 °C(lit.)
• Flash Point: 107.7 °C
• Appearance: monoclinic needles from water
• Density: 1.1227 (rough estimate)
• Vapor Pressure: 0.0026mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in chloroform, methanol.
• Sensitive: Light Sensitive
• BRN: 1910606
• CAS DataBase Reference: alpha-Asarone(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Asarone(2883-98-9)
• EPA Substance Registry System: alpha-Asarone(2883-98-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DC2975000
• Hazardous Substances Data: 2883-98-9(Hazardous Substances Data)

Usage

Description

Alpha-Asarone, also known as the trans-isomer of asarone, is a toxic morphogenetic agent that can be naturally extracted from Acorus calamus. It is considered a growth inhibitor and acts as an antifeedant with relatively low toxicity. Alpha-Asarone possesses various pharmacological properties, including neuroprotective, anti-oxidative, anticonvulsive, and cognitive-enhancing actions.

Uses

Used in Pharmaceutical Industry:
Alpha-Asarone is used as a key compound in the synthesis of a series of alpha-asarone isomers, which have been investigated for their hypolipidemic and antiplatelet activities. These properties make it a valuable component in the development of medications for treating various health conditions.
Used in Synthesis of Anti-inflammatory Agents:
In the field of organic chemistry, alpha-Asarone is utilized in the synthesis of anti-inflammatory neolignan compounds, which are known for their potential therapeutic effects in reducing inflammation.
Used in Synthesis of Antiallergic Agents:
Alpha-Asarone is also employed in the synthesis of lignan compounds, which are used as antiallergic agents. These agents can help alleviate symptoms associated with allergic reactions.
Used in Treatment of Neurological Conditions:
Clinically, alpha-Asarone is used as a medication for treating epilepsy, cough, bronchitis, and asthma. Its neuroprotective, anti-oxidative, anticonvulsive, and cognitive-enhancing properties make it a valuable asset in managing these conditions.
Used in Chemosterilants and Oviposition Stimulants:
In addition to its pharmaceutical applications, alpha-Asarone is known for its chemosterilant and oviposition stimulant properties, which can be useful in various biological and ecological research applications.

InChI:InChI=1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

Upstream product

• 4460-86-0 asaraldehyde 
• 137-40-6 sodium proprionate 
• 123-62-6 propionic acid anhydride 
• 5273-86-9 C₁₂H₁₆O₃ 
• 7732-18-5 water 
• 7446-08-4 selenium(IV) oxide 
• 64-17-5 ethanol 
• 29652-82-2 1-(2,4,5-Trimethoxyphenyl)propan-1-ol 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 5353-15-1 1-allyl-2,4,5-trimethoxybenzene 
• 1398321-45-3 benzenesulfonic acid 2-(2-bromo-4,5-dimethoxyphenyl)-1-methylethyl ester 
• 494-40-6 asarone 

Downstream Products

• 134040-35-0 2,4,5-trimethoxy-β-methyl-β-nitrostyrene 
• 80434-33-9 γ-diasarone 
• 146830-05-9 1-(2,4,5-Trimethoxyphenyl)-1,2-dihydroxypropane 
• 5273-86-9 C₁₂H₁₆O₃ 
• 4460-86-0 asaraldehyde 
• 82645-86-1 3-Methoxy-3-(2,4,5-trimethoxyphenyl)-propan 
• 70280-35-2 Heterotropan 
• 70280-35-2 andamanicin 
• 1072432-04-2 magnoshinin 
• 70280-35-2 C₂₄H₃₂O₆ 
• 93376-03-5 (±)-magnosalicin 
• 93376-03-5 (2R,3S,4R,5S)-2,4-Dimethyl-3,5-bis-(2,4,5-trimethoxy-phenyl)-tetrahydro-furan 
• 93376-03-5 (2S,3S,4R,5S)-2,4-Dimethyl-3,5-bis-(2,4,5-trimethoxy-phenyl)-tetrahydro-furan 
• 93376-03-5 (2S^*,3S^*,4R^*,5R^*)-2,4-dimethyl-3,5-bis(2',4',5'-trimethoxyphenyl)tetrahydrofuran 

Relevant articles and documents

Sustainable Synthesis of the Naturally Hypolipidemic Agent α-Asarone

(Chemical Equation Presented). A short and practical preparation of α-asarone was developed using the inexpensive methylisoeugenol as a starting material. The utilization of a sequence of tribromination, debromination, and copper-mediated aromatic substitution enabled the stereoselective formation of only the E-isomer of α-asarone in good yield.

A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.

Green and simple preparation process of alpha-asarone

The invention relates to the technical field of medicine, in particular to a green and simple preparation process of alpha-asarone. 1,2,4-trimethoxybenzene is adopted as a raw material, and three steps, namely, an acylation reaction, a reduction reaction and a dehydration reaction are included. Through the preparation process of alpha-asarone, the total yield can reach 62.3% or above, all organicsolvents can be recycled repeatedly, and the process has the advantages of low cost, small pollution, safe and convenient operation, high yield and the like.