| Identification | More | [Name]
Piperonylic acid | [CAS]
94-53-1 | [Synonyms]
1,3-BENZODIOXOLE-5-CARBOXYLIC ACID
3,4-METHYLENDIOXYBENZOIC ACID
3,4-(METHYLENEDIOXY)BENZOIC ACID
AKOS 213-90
PIPERONYLIC ACID
PROTOCATECHUIC ACID METHYLENETHER
RARECHEM AL BO 0210
TIMTEC-BB SBB003897
3,4-dioxymethylenebenzoicacid
5-benzodioxolecarboxylicacid
Benzoic acid, 3,4-(methylenedioxy)-
Heliotropic acid
heliotropicacid
Protocatechuic acid methylene ether
3,4-(methylenedioxy)benzoic acid, piperonylic acid
Piperonylic acid, 98+%
PIPEROYLICACID
3,4-Methylendioxybenzoic acid 98%
β(3,4-methylenedioxy-styryl)acrylic acid
1,3-Benzodioxole-5-carboxylic acid 98% | [EINECS(EC#)]
202-342-8 | [Molecular Formula]
C8H6O4 | [MDL Number]
MFCD00005830 | [Molecular Weight]
166.13 | [MOL File]
94-53-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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) | [form ]
Powder | [pka]
4.35±0.20(Predicted) | [color ]
Off-white to beige | [Water Solubility ]
slightly soluble | [Detection Methods]
HPLC,NMR | [Merck ]
14,7477 | [BRN ]
150206 | [Cosmetics Ingredients Functions]
SKIN PROTECTING
SKIN CONDITIONING | [InChI]
1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10) | [InChIKey]
VDVJGIYXDVPQLP-UHFFFAOYSA-N | [SMILES]
OC(=O)c1ccc2OCOc2c1 | [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]
94-53-1(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [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. |
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