Piperonylic acid Chemical Properties

Melting point:

229-231 °C (lit.)

Boiling point:

254.32°C (rough estimate)

Density 

1.3579 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.35±0.20(Predicted)

form 

Powder

color 

Off-white to beige

Water Solubility 

slightly soluble

Merck 

14,7477

BRN 

150206

LogP

0.810 (est)

CAS DataBase Reference

94-53-1(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Benzodioxole-5-carboxylic acid(94-53-1)

EPA Substance Registry System

1,3-Benzodioxole-5-carboxylic acid (94-53-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

RTECS 

DF4912765

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29329970

MSDS

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Piperonylic acid Usage And Synthesis

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.

Piperonylic acid(94-53-1)Related Product Information

• (Trifluoromethoxy)benzene
• Citric acid
• 1,3-Benzodioxole
• 4-Methoxybenzoic acid
• Glycine
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Anisole
• Methoxydiethylborane
• Black Pepper Oil
• 2-Benzoylbenzoic acid
• Alginic acid
• Dextrin
• 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID
• Arachidic acid
• Ascoric Acid
• Aristolochic acid
• Piperonylic acid hydrazide