TRANS-2-METHYL-2-BUTENAL

Description

2-Methyl-2-butenal has a penetrating, powerful green ethereal odor. May be prepared by condensation of acetaldehyde and propionaldehyde.

Description

The allure of pheromones tantalizes scientists in many fields. What can be more intriguing than chemicals produced by animals with the sole purpose of changing the behavior of fellow creatures? Researchers have cast their nets widely to identify the chemistry of pheromones, and often, the results are surprising.
(E)-2-Methyl-2-butenal is a conjugated unsaturated aldehyde. Its structure is that of the more familiar crotonaldehyde with an additional methyl group. It is a colorless liquid with a boiling range of 116–119 °C. Synthetic (E)-2-methyl-2-butenal is used primarily as a source of a four–carbon-atom chain in organic synthesis.
In 2003, French researcher Benoist Schaal and colleagues discovered that the compound is a mammary pheromone used by lactating female rabbits to guide their young toward the breast. More recently, Schaal’s group observed a similar attraction between the breast secretions of lactating women and their infants.
There are other suspected pheromonal attractions between men and women. Although?no specific human pheromone has been identified?to date, the search goes on.

Chemical properties

trans-2-Methyl-2-butenal is a clear colorless to yellow liquid. B.P. 135℃. Sp.Gr. 0.87. Almost insoluble in water, soluble in alcohol and oils. Powerful and very diffusive, penetrating “gassy” odor of green-ethereal character. Very poor tenacity.

The Uses of TRANS-2-METHYL-2-BUTENAL

Tiglic aldehyde was used in the concise total synthesis of 7-demethylpiericidin A1. It was used as starting reagent during the synthesis of:

• alkyl-branched tetraene hydrocarbons, pheromone component for dried fruit beetle
• E,E-2,4-dimethyl-2,4-hexa dienal, volatile constituents of the defensive secretions of Leiobunum nigripalpi
• 4-methyl-2,4-hexadiene-1-ol

General Description

trans-2-Methyl-2-butenal is one of the major volatile constituents of coriander and olive oil.