3-phenylprop-2-enal

• ChemBase ID: 92763
• Molecular Formular: C9H8O
• Molecular Mass: 132.15922
• Monoisotopic Mass: 132.05751488
• SMILES: O=C/C=C/c1ccccc1
• Canonical SMILES: O=C/C=C/c1ccccc1
• InChI: InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H
• InChIKey: KJPRLNWUNMBNBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-phenylprop-2-enal; (2E)-3-phenylprop-2-enal
• IUPAC Traditional name: 3-phenyl-2-propenal; cinnamal
• Synonyms: Cinnamaldehyde; trans-3-Phenyl-2-propenal; trans-Cinnamaldehyde; (2E)-3-Phenylprop-2-enal; trans-Cinnamaldehyde; Cinnamic aldehyde; trans-cinnamaldehyde; Cinnamaldehyde; Cinnamaldehyde; 3-Phenylprop-2-enal; CINNAMIC ALDEHYDE; trans-3-Phenylacrolein; 3-苯基丙-2-烯醛; 3-苯基-2-丙烯醛; 反式肉桂醛; 反-肉桂醛

Database IDs

• CAS Number: 14371-10-9; 104-55-2
• EC Number: 203-213-9
• MDL Number: MFCD00007000
• Beilstein Number: 1071571
• Merck Index: 142297
• PubChem SID: 162079461; 24890286; 24900953; 24854395; 24893018; 24900954
• PubChem CID: 637511
• CHEBI ID: 16731
• CHEMBL: 293492
• Chemspider ID: 553117
• FEMA ID: 2286
• IUPHAR ligand ID: 2423
• KEGG ID: C00903
• Unique Ingredient Identifier: SR60A3XG0F
• Wikipedia Title: Cinnamaldehyde
• Council of Europe Number: 102c; 102
• Flavis Number: 5.014

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.97747
• LogD (pH = 7.4): 1.97747
• Log P: 1.97747
• Molar Refractivity: 42.1345 cm^3
• Polarizability: 15.781555 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly Soluble in water
• Apperance: Oil; Yellow oil
• Melting Point: -7.5 °C; -7.5°C; -7.5 °C; -8°C; -9--4 °C(lit.)
• Boiling Point: 246 °C at 1014 hPa; 248 °C(lit.); 248°C; 248 °C; 250-252 °C(lit.); 250-252°C
• Flash Point: 120 °C (closed cup); 125 °C; 131°C(268°F); 159.8 °F; 257 °F; 71 °C; 71°C; 71 °C
• Density: 1.0497 g/cm^3 at 20 °C; 1.05 g/mL; 1.05 g/mL at 25 °C(lit.); 1.050
• Refractive Index: 1.6220; n20/D 1.621(lit.); n20/D 1.622; n20/D 1.622(lit.)
• Vapor Pressure: 2.25 hPa at 20 °C
• Vapor Density: 4.6 (vs air)
• Viscosity: ? cP at ?°C
• Organoleptic: cinnamon; clove; spicy; cinnamon; clove; spicy; sweet; vanilla

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• Storage Warning: Air Sensitive; Irritant/Keep Cold/Air Sensitive/Store under Argon
• RTECS: GD6475000; GD6476000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 1; 3
• Packing Group: None
• Australian Hazchem: 3YE
• Risk Statements: 36/37/38-43; 36/38-43; R:10-36/37/38; R36 R37 R38
• Safety Statements: 24-26-37; 26-36/37; S:16-20-25-26-37/39; S26 S36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  2

  2

  0
• GHS Hazard statements: H315-H317-H319-H335; H315-H319-H317-H303-H313
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P280G-P262-P305+P351+P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (182.60)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥93%; ≥95.0% (GC); ≥98%; ≥98.0% (GC); ≥99%; 95+%; 98+%; 99%
• Grade: analytical standard; FG; Halal; Kosher; natural; NI; purum
• Impurities: ≤1% cinnamic acid
• Biological Source: from cassia oil
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: C6H5CH=CHCHO

DETAILS

MP Biomedicals - 02150690

Purity: 99%
1 ml = approx. 1.05 g

Sigma Aldrich - C80687

Packaging
1 kg in poly bottle
25, 500 g in poly bottle

Sigma Aldrich - 239968

Packaging
50 g in glass bottle

Sigma Aldrich - W228605

Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum
Application
Buildingblock - Cinnamaldehyde is an unsaturated aldehyde so it can easily react to many different compounds to be used in a wide range of fragrance compositions. It is also a building block for several agrochemicals (miticides) or for derivatives like cinnamic alcohol, 3-phenylpropanol, cinnamonitrile, 3-phenylpropionylaldehyde (fragrances and as an alternative to enalapril, lisinopril and ramipril).

Sigma Aldrich - W228613

Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in comp drum
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. W228613.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• For reaction with 1,2-Ethanedithiol, L12865 to give the dithiolane, followed by coupling with trimethylsilylmethyl magnesium chloride, catalyzed by Dichlorobis(triphenylphosphine)nickel(II), 13930, as an example of Ni catalyzed coupling of dithioacetals with Grignards, see: J. Org. Chem., 53, 5582 (1988); Org. Synth. Coll., 9, 727 (1998):
  
• For details of the 1,2-addition of a functionalized Zn-Cu organometallic RCu(CN)ZnI to give an allylic alcohol, see; Org. Synth. Coll., 9, 502 (1998).