CAS 2373-80-0 3-(1,3-Benzodioxol-5-yl)prop-2-enoic acid (HCID 16917)

Substructure search Find similar structures

Basic information

CAS: 2373-80-0
Standard SMILES: O=C(O)C=Cc1ccc2c(c1)OCO2
InChIKey: QFQYZMGOKIROEC-UHFFFAOYSA-N
Molecular formula: C10H8O4
Average molar mass: 192.17 g/mol
Monoisotopic mass: 192.04225874

Overview

3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid has been reported in Brombya platynema and Helichrysum arenarium with data available.

Names & identifiers

Preferred name: 3-(1,3-Benzodioxol-5-yl)prop-2-enoic acid
IUPAC: 3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
English name: 3,4-(Methylenedioxy)cinnamic acid
Molecular formula: C10H8O4
Molecular weight: 192.17

Names & synonyms

2373-80-03,4-Methylenedioxy Cinnamic Acid3-(1,3-benzodioxol-5-yl)prop-2-enoic acid3-benzo[1,3]dioxol-5-yl-acrylic acid4-MethylendioxyzimtsaureEnamine_0010773,4-(Methylenedioxy)cinnamic acid, predominantly transSCHEMBL794283,4methylenedioxycinnamic acidorb1298147orb1940224SCHEMBL29644896

Show more names

AKOS B004102AKOS AUF01566AKOS BBS-00006476RARECHEM BK HC S236PiperonylideneaceticPIPERONYL ACRYLIC ACID3-PIPERONYLACRYLIC ACID3,4-Methoxy cinnaMic acidPiperonylideneacetic acid.Acetic acid, piperonylidene-

3,4-methylenedioxy-cinnamic acidQFQYZMGOKIROEC-UHFFFAOYSA-NDTXSID7010199063',4'-Methylenedioxycinnamic acid3-benzo-1,3-dioxol-5-ylacrylic acidAKOS0172686623-Benzo[1,3] dioxol-5-yl-acrylic acidPD211457

Database identifiers

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 55.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 249

Physicochemical properties

Melting point: 242 · 242-244 °C (dec.)(lit.)
Boiling point: 248.14 °C · 248.14°C (rough estimate)
Density: 1.0825 · 1.0825 (rough estimate)
refractive index: 1.444 · 1.4440 (estimate)
storage temp.: Inert atmosphere,Room Temperature
solubility: very faint turbidity in Pyridine
form: powder to crystal
pka: 4.37 · 4.37±0.10(Predicted)
color: White to Light yellow
BRN: 84599 · 84599
InChI: InChI=1S/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)
InChIKey: QFQYZMGOKIROEC-DUXPYHPUSA-N
SMILES: C(O)(=O)C=CC1=CC=C2OCOC2=C1
CAS DataBase Reference: 2373 · 2373-80-0(CAS DataBase Reference)
FDA UNII: 8 H0WPJ08Y · X8H0WPJ08Y

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29329990
risk_code: 38-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 36-24/25-37-26
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H335-H315-H319
REACH Registrations: Active
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications

Uses3,4-(Methylenedioxy)cinnamic acid, predominantly trans is an inhibitor of the phenylpropanoid enzyme 4-hydroxycinnamoyl-CoA ligase.

General Description3,4-(Methylenedioxy)cinnamic acid is an inhibitor of the phenylpropanoid enzyme 4-hydroxycinnamoyl-CoA ligase. It undergoes electron transfer reaction with trichloromethylperoxyl radical and reaction has been studied by pulse radiolysis.