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Bluer and better: Improving the water solubility and acid stability of guaiazulene

Bluer and better: Improving the water solubility and acid stability of guaiazulene
(a) Synthesis of guaiazulene substituted poly(allylamine) (b) Photo of guaiazulene substituted poly(allylamine). Credit: New Journal of Chemistry (2025). DOI: 10.1039/D5NJ01214G

Guaiazulene belongs to the class of azulene compounds, known for their vibrant blue color. Guaiazulene produces a blue color more saturated than that of naturally derived blue pigments and contains antioxidant properties.

Although it is often found in topical creams for skincare, it has also been touted as a potential food coloring agent. Yet this potential has been stymied because of its poor water solubility and color degradation under acidic conditions.

A group of researchers, however, has overcome this common stumbling block by introducing guaiazulene into a hydrophilic poly(allylamine).

Details of the team's breakthrough are in the New Journal of Chemistry.

"We prepared a carboxylic , a common type of acid found in many citrus fruits and vinegars, with a guaiazulene skeleton, which can be easily condensed with amines," explains Kouki Oka, an associate professor at Tohoku University who led the research group.

"We then synthesized a blue polymer, incorporating the guaiazulene skeleton into the side chain. The synthesis was carried out by reacting the carboxylic acid with a highly hydrophilic poly(allylamine) condensation agent."

The guaiazulene introduction degree was easily adjustable by changing the equivalent amount of carboxylic acid with the guaiazulene skeleton. The polymer with a 3.2% introduction degree was more than 10,000 times more water-soluble than guaiazulene alone.

Bluer and better: Improving the water solubility and acid stability of guaiazulene
UV-vis spectra of acidic solution (mixture of buffer solution (pH 4) and ethanol) of (a) Guaiazulene and (b) guaiazulene substituted poly(allylamine). Credit: New Journal of Chemistry (2025). DOI: 10.1039/D5NJ01214G

Oka and his colleagues also measured the absorption spectra of guaiazulene and guaiazulene-substituted poly(allylamine) in acidic solution. While the absorption spectrum of guaiazulene changed significantly in shape and maximum wavelength after one month, the absorption spectrum of guaiazulene-substituted poly(allylamine) showed no significant change.

This indicated that the introduction of guaiazulene into poly(allylamine) improves its stability under acidic conditions.

Oka believes that the results will lead to more than just the development of blue colorants under acidic conditions. "This could lead to the development of new functions for hydrophobic and acid-sensitive materials, something that has been difficult to achieve in the past."

More information: Yo Kinoshita et al, Hydrophilization of guaiazulene-based blue pigment: improving its stability in acidic conditions by substitution with polyallylamine, New Journal of Chemistry (2025).

Provided by Tohoku University

Citation: Bluer and better: Improving the water solubility and acid stability of guaiazulene (2025, June 4) retrieved 6 June 2025 from /news/2025-06-bluer-solubility-acid-stability-guaiazulene.html
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