1,3-Benzodioxole-5-carboxylic acid

HCID 7196CAS 94-53-1
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(O)c1ccc2c(c1)OCO2
InChIKey
VDVJGIYXDVPQLP-UHFFFAOYSA-N
Molecular formula
C8H6O4
Average molar mass
166.13 g/mol
Monoisotopic mass
166.02660867

Overview

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.

Names & identifiers

Preferred name
1,3-Benzodioxole-5-carboxylic acid
IUPAC
1,3-benzodioxole-5-carboxylic acid
English name
Piperonylic acid
Molecular formula
C8H6O4
Molecular weight
166.13

Names & synonyms

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
Show more names
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

Database identifiers

CAS
94-53-1
PubChem CID
7196
DTXSID
DTXSID6059104
ChEMBL
CHEMBL573781
ChEBI
CHEBI:107644
UNII
QX3V1NO0KH
EC Number
202-342-8
Nikkaji
J4.700G

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
55.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point229 °C
Physical Description · 2 items

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]

Physicochemical properties

Melting point
229 · 229-231 °C (lit.)
Boiling point
254.32 °C · 254.32°C (rough estimate)
Density
1.3579 · 1.3579 (rough estimate)
refractive index
1.509 · 1.5090 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
DMSO (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 2 items

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%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DF4912765
hs_code
29329970
risk_code
22-37/38-41-36/37/38

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

UsesFound in Paracoto bark; [Merck Index]
General Manufacturing Information1,3-Benzodioxole-5-carboxylic acid: ACTIVE

Applications

UsesPiperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

152 records
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Linked notes

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