(2E)-3-phenylprop-2-enoic acid

• ChemBase ID: 81003
• Molecular Formular: C9H8O2
• Molecular Mass: 148.15862
• Monoisotopic Mass: 148.0524295
• SMILES: OC(=O)/C=C/c1ccccc1
• Canonical SMILES: OC(=O)/C=C/c1ccccc1
• InChI: InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)
• InChIKey: WBYWAXJHAXSJNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-phenylprop-2-enoic acid; 3-phenylprop-2-enoic acid
• IUPAC Traditional name: cinnamic acid; phenylacrylic acid
• Synonyms: Cinnamic Acid; trans-Cinnamic Acid; Phenylacrylic acid; Cinnamylic acid; 3-Phenylacrylic acid; (E)-Cinnamic acid; Benzenepropenoic acid; Isocinnamic acid; Cinnamic acid; HEPARIN LITHIUM SALT; β-Phenylacrylic acid; 3-Phenyl-2-propenoic acide; Cinnamic acid; (2E)-3-Phenylprop-2-enoic acid; (E)-3-Phenylacrylic acid; trans-Cinnamic acid; trans-3-Phenylacrylic acid; trans-Cinnamic acid; 反式-3-苯基丙烯酸; 肉桂酸; 反式肉桂酸; 反-肉桂酸

Database IDs

• CAS Number: 621-82-9; 140-10-3; 9045-22-1
• EC Number: 210-708-3; 205-398-1
• MDL Number: MFCD00004369
• Beilstein Number: 1905952
• Merck Index: 142299
• PubChem SID: 24890291; 162068122; 24900955; 24900956; 24893022; 24848120
• PubChem CID: 444539
• CHEBI ID: 35697
• CHEMBL: 27246
• Chemspider ID: 392447
• FEMA ID: 2288
• KEGG ID: C00423
• Wikipedia Title: Cinnamic_acid
• Council of Europe Number: 22; 22c
• Flavis Number: 8.022

CALCULATED PROPERTIES

• Acid pKa: 4.509232
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.1043326
• LogD (pH = 7.4): -0.6654147
• Log P: 2.1360862
• Molar Refractivity: 43.0599 cm^3
• Polarizability: 16.190388 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 500 mg/L in water
• Apperance: Powder; White monoclinic crystals
• Melting Point: 132-135 °C(lit.); 132-135°C; 133 °C(lit.); 133°C; 133-136°C; 133-137 °C
• Boiling Point: 147°C/4mm; 147°C/4mm; 300 °C(lit.); 300°C
• Flash Point: 100 °C; 100°C; 100°C (212°F) >; 166°C(330°F); 212 °F
• Density: 1.2475 g/cm^3; 1.248 g/ml; 1.250
• pKa: 4.44
• Organoleptic: cinnamon; honey; floral; spicy; sweet; honey; floral

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Irritant
• RTECS: GD7800000; GD7850000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36; 36/37/38; R36
• Safety Statements: 26; 26-36; S25
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: H315-H319-H335; H319-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥99%; ≥98.0% (HPLC); ≥99%; ≥99.0% (T); 95+%; 97%; 98%; 99+%
• Grade: analytical standard; FG; Halal; Kosher; natural; NI; purum
• Linear Formula: C6H5CH=CHCOOH
• Empirical Formula (Hill Notation): C9H8O2

DETAILS

MP Biomedicals - 05211131

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101929

From Porcine Intestinal Mucosa
Lithium Salt
Based on 100 u/mg. Actual activity supplied with each shipment.

MP Biomedicals - 02101243

Light tan crystals
Purity: 99+%

Sigma Aldrich - W228826

Packaging
1 kg in poly bottle
25 g in glass bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - 133760

Packaging
100, 500 g in poly bottle
2 kg in poly drum

Sigma Aldrich - C80857

Packaging
250 g in poly bottle
5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C80857.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C80857.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - W228818

Packaging
1 kg in poly bottle
10 kg in poly drum
1 sample in glass bottle
25 kg in fiber drum

REFERENCES

• Heating with excess thionyl chloride and a catalytic amount of pyridine gives a benzo[b]thiophene derivative, formed by electrophilic addition of thionyl chloride across the double bond of cinnamoyl chloride, Pummerer rearrangement of the resulting sulfinyl chloride and final cyclization. ɑ-Chlorocinnamoyl chloride is formed as a by-product by elimination of SCl₂: J. Org. Chem., 40, 3037 (1975):
  
• Under similar conditions, 3-phenylpropionic acid gave the same products in lower yield; the reaction was thought to occur via an initial ɑ-enolization of the acid chloride: Tetrahedron Lett., 5149 (1968).