Chemical Properties
It is a white to light yellow crystalline powder, slightly soluble in water, chloroform, cold ethanol, and ether.
Uses
Piperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.
Definition
ChEBI: Piperonylic acid is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties. It has a role as a plant metabolite, an EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor, a vulnerary and an antifungal agent. It is a member of benzodioxoles, a monocarboxylic acid and an aromatic carboxylic acid. It is a conjugate acid of a piperonylate.
Synthesis Reference(s)
The Journal of Organic Chemistry, 40, p. 3803, 1975
DOI: 10.1021/jo00913a051
Purification Methods
Crystallise the acid from EtOH or water. [Beilstein 19/7 V 300.]
References
[1] OTTO RICHARD GOTTLIEB MAURO T M. Isolation of Piperonylic Acid from Ocotea pretiosa[J]. Nature, 1958, 182 4637: 742-743. DOI:10.1038/182742b0.
[2] SEUNG HYUN HAN. Piperonylic Acid Promotes Hair Growth by Activation of EGFR and Wnt/β-Catenin Pathway.[J]. International Journal of Molecular Sciences, 2024, 25 19. DOI:10.3390/ijms251910774.
[3] SCHALK. Piperonylic acid, a selective, mechanism-based inactivator of the trans-cinnamate 4-hydroxylase: A new tool to control the flux of metabolites in the phenylpropanoid pathway[J]. Plant Physiology, 1998, 118 1: 209-218. DOI:
10.1104/pp.118.1.209.
