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

• ChemBase ID: 52498
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: C(=O)(CCc1cc2c(cc1)OCO2)O
• Canonical SMILES: OC(=O)CCc1ccc2c(c1)OCO2
• InChI: InChI=1S/C10H10O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1,3,5H,2,4,6H2,(H,11,12)
• InChIKey: UIYJGLLTSVRSBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2H-1,3-benzodioxol-5-yl)propanoic acid
• IUPAC Traditional name: 3-(2H-1,3-benzodioxol-5-yl)propanoic acid
• Synonyms: 3,4-(Methylenedioxy)-hydrocinnamic Acid; 1,3-Benzodioxole-5-propionic Acid; 3-(3,4-Methylenedioxyphenyl)propionic Acid; 3-(Benzo[d][1,3]dioxol-5-yl)propanoic Acid; 3-(Benzodioxol-5-yl)propionic Acid; 3-[Benzo[1,3]dioxol-5-yl]propionic Acid; NSC 55524; 1,3-Benzodioxole-5-propanoic Acid; 1,3-Benzodioxole-5-propanoic acid; 3,4-(methylenedioxy)hydrocinnamic acid; 3,4-Methylenedioxydihydrocinnamic acid; 3-(3,4-Methylenedioxyphenyl)propionic acid; 3-(1,3-benzodioxol-5-yl)propanoic acid; 3-(3,4-Methylenedioxyphenyl)propionic acid; 3-(1,3-Benzodioxyl-5-yl)propionic acid; 1,3-苯并二噁茂-5-丙酸; 3,4-亚甲基二氧基二氢肉桂酸; 3-(亚甲基二氧基)氢化肉桂酸; 3-(3,4-亚甲二氧基苯基)丙酸

Database IDs

• CAS Number: 2815-95-4
• EC Number: 220-565-9
• MDL Number: MFCD00016909
• Beilstein Number: 181735
• PubChem SID: 162057261; 24884299
• PubChem CID: 64810

CALCULATED PROPERTIES

• Acid pKa: 3.7346468
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.086536005
• LogD (pH = 7.4): -1.6123849
• Log P: 1.6787963
• Molar Refractivity: 47.7335 cm^3
• Polarizability: 18.882221 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Grey Solid
• Melting Point: 83-87 °C; 86 - 88°C; 86-88°C; 87-88°C
• Hydrophobicity(logP): 1.468

Safety Information

• Storage Warning: IRRITANT
• RTECS: MW5600000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 98%; 99%
• Linear Formula: C10H10O4

DETAILS

Sigma Aldrich - 657565

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B203505

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)
• Conversion to the dianion and iodination gives the ɑ-iodo-derivative, a precursor of a wide range of lignans, in good yield: Synth. Commun., 18, 699 (1988).