3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid

• ChemBase ID: 28605
• Molecular Formular: C10H8O4
• Molecular Mass: 192.16812
• Monoisotopic Mass: 192.04225874
• SMILES: c12c(OCO1)ccc(/C=C/C(=O)O)c2
• Canonical SMILES: OC(=O)/C=C/c1ccc2c(c1)OCO2
• 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)/b4-2+
• InChIKey: QFQYZMGOKIROEC-DUXPYHPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid; (2E)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
• IUPAC Traditional name: 3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid; (2E)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
• Synonyms: 3,4-(Methylenedioxy)cinnamic acid, predominantly trans; (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic acid; 3-(1,3-benzodioxol-5-yl)acrylic acid; 3-(1,3-Benzodioxol-5-yl)propenoic acid; (E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic Acid; (2E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic Acid; (E)-3,4-(Methylenedioxy)cinnamic Acid; (E)-3-(3,4-Methylenedioxyphenyl)acrylic Acid; 3-(3,4-Methylenedioxyphenyl)-2E-propenoic Acid; trans-3,4-(Methylenedioxy)cinnamic Acid; trans-3-(3,4-Methylenedioxyphenyl)-2-propenoic Acid; (2E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic Acid; (2E)-3-(1,3-Benzodioxol-5-yl)acrylic acid; 3-(Benzo[d][1,3]dioxol-5-yl)acrylic acid; 3,4-(亚甲二氧)肉桂酸，反式为主; 3,4-(亚甲二氧基)肉桂酸, 主体成分为反式

Database IDs

• CAS Number: 38489-76-8; 2373-80-0
• EC Number: 219-151-0
• MDL Number: MFCD00005837
• Beilstein Number: 84599
• PubChem SID: 160991912; 24848770
• PubChem CID: 643181

CALCULATED PROPERTIES

• Acid pKa: 3.5510597
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.18321599
• LogD (pH = 7.4): -1.6001791
• Log P: 1.7593198
• Molar Refractivity: 48.8268 cm^3
• Polarizability: 18.701979 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Off-white Solid
• Melting Point: 242-244 °C (dec.)(lit.); ca 243°C dec.

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 99%
• Empirical Formula (Hill Notation): C10H8O4
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 146242

Packaging
25 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - B203520

Substituted cinnamic and dihydrocinnamic acids show anti-inflammatory and analgesic activity, with cinnamic acids being more biologically active.

REFERENCES

• Runwal, L. et al.: Eastern Pharmacist 38, 141 (1995)