4-Vinylanisole

November 02, 2020
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4-Vinylanisole (4VA)鈥攆requently also called 4-methoxystyrene鈥攊s a naturally occurring aroma compound. Among other sources, it is one of the , which is obtained by fermenting the juice of the mirabelle plum (Prunus domestica subsp. syriaca).

Beyond the brandy connection, 4VA is the center of a more spectacular natural phenomenon. This year, Xianhui Wang, Le Kang, and six collaborators at the Chinese Academy of Sciences (Beijing) reported that responsible for locust swarms, such as those that recently devastated large portions of East Africa.

When solitary migratory locusts (Locusta migratoria) form small groups, they begin to emit 4VA, attracting additional insects. As the locusts aggregate, the 4VA signal becomes stronger, and the swarm grows exponentially. This year鈥檚 swarm鈥攕ome call it a 鈥淏iblical plague鈥濃攃overed thousands of square kilometers, mostly in Kenya and Ethiopia, but also in other African and Middle Eastern countries.

4VA鈥檚 aggregation pheromone property might have a positive side. Instead of using pesticides to control the locusts, 4VA could potentially be used as a bait to trap the insects before they begin the swarming process, according to Wang, Kang, et al. The researchers also found that a genetic modification prevented locusts from detecting 4VA signals; but others in the field warn against unintended consequences from this sort of alteration.

4-Vinylanisole聽hazard information

Hazard class*Hazard statement
Flammable liquids, category 4H227鈥擟ombustible liquid聽Chemical Safety Warning
Skin corrosion/irritation, category 2H315鈥擟auses skin irritationChemical Safety Warning
Serious eye damage/eye irritation, category 2聽H319鈥擟auses serious eye irritationChemical Safety Warning

* Globally Harmonized System of Classification and Labeling of Chemicals.

MOTW update:聽February 29, 2024

4-Vinylanisole1 (4VA. aka 4-methoxystyrene) was the Molecule of the Week for November 2, 2020. It is an aroma compound particularly known as a volatile component of a French brandy. In 2020, Chinese researchers reported that 4VA is a locust pheromone that causes the insects to swarm.

This month, Hong Pan, Daoyi Guo, and co-workers at Gannan Normal University (Ganzhou, China) described a . They used engineered Escherichia coli as the host organism to synthesize the pheromone from erythrose-4-phosphate2 and phosphoenolpyruvate3. The authors state that their synthetic method is an improvement over current chemical methods for producing 4VA and would increase the supply of the compound for capturing locusts and monitoring their population dynamics.

1. CAS Reg. No. 637-69-4.
2. CAS Reg. No. 138-08-9.
3. CAS Reg. No. 585-18-2.

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4-Vinylanisole fast facts

CAS Reg. No.637-69-4

nomenclature
Benzene, 1-ethenyl-4-methoxy-
Empirical formulaC9H10O
Molar mass134.18 g/mol
AppearanceColorless liquid
Boiling Point205 潞C
Water solubility聽Insoluble

A question for readers

Fun fact: 4VA and water have essentially the same density under ambient conditions. What, if anything, are we to make of this?聽Please send your thoughts to聽motw@acs.org.

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