Piperonylsure
1,3-Benzodioxole-5-carboxylic acid
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Grundinformationen
- CAS
94-53-1- Standard-SMILES
O=C(O)c1ccc2c(c1)OCO2- InChIKey
VDVJGIYXDVPQLP-UHFFFAOYSA-N- Summenformel
- C8H6O4
- Durchschnittliche Molmasse
- 166,13 g/mol
- Monoisotopische Masse
- 166,02660867
Überblick
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 an EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor, an antifungal agent, a vulnerary and a plant metabolite. It is a monocarboxylic acid, an aromatic carboxylic acid and a member of benzodioxoles. It is a conjugate acid of a piperonylate.
Namen und Bezeichner
- Bevorzugter Name
- 1,3-Benzodioxole-5-carboxylic acid
- IUPAC
- 1,3-benzodioxole-5-carboxylic acid
- Lokaler Name
- Piperonylsure
- Englischer Name
- Piperonylic acid
- Summenformel
- C8H6O4
- Molmasse
- 166.13
Namen und Synonyme
PIPERONYLIC ACID94-53-11,3-Benzodioxole-5-carboxylic acidHeliotropic acid2H-1,3-Benzodioxole-5-Carboxylic Acid3,4-(Methylenedioxy)benzoic acidProtocatechuic acid methylene ether5-Benzodioxolecarboxylic acid3,4-Dioxymethylenebenzoic acidQX3V1NO0KHDTXSID6059104NSC-10072
Weitere Namen anzeigen
PIPEROYLICACIDAKOS 213-90Pepper acidheliotropicacidPiperonylicAcid>
CHEBI:107644RefChem:863626DTXCID7048902202-342-8Benzo[d][1,3]dioxole-5-carboxylic acid3,4-Methylenedioxybenzoic acidMFCD00005830benzo[1,3]dioxole-5-carboxylic acid
Datenbank-Bezeichner
- CAS
94-53-1- PubChem CID
- 7196
- DTXSID
DTXSID6059104- ChEMBL
CHEMBL573781
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,4
- Polarare Oberfläche (TPSA)
- 55,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 191
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Organic Acids
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point229 °C
Physical Description
Solid; [Merck Index] White powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section124.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 229 · 229-231 °C (lit.)
- Siedepunkt
- 254.32 °C · 254.32°C (rough estimate)
- Dichte
- 1.3579 · 1.3579 (rough estimate)
- Brechungsindex
- 1.509 · 1.5090 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 11-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19383
1,3-Benzodioxole-5-carboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryIntraperitoneal LD50 (mouse) > 800 mg/kg; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (89.1%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329970
- RTECS-Nr.
- DF4912765
- risk_code
- 22-37/38-41-36/37/38
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37/39-37/39
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Verwendung und Herstellung
UsesFound in Paracoto bark; [Merck Index]
General Manufacturing Information1,3-Benzodioxole-5-carboxylic acid: ACTIVE
Anwendungen
VerwendenPiperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.
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