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HomeProduct name listPhenylpropyl aldehyde

Phenylpropyl aldehyde

Synonym(s):3-Phenylpropanal;3-Phenylpropionaldehyde;Hydrocinnamaldehyde, 3-Phenylpropanal

  • CAS NO.:104-53-0
  • Empirical Formula: C9H10O
  • Molecular Weight: 134.18
  • MDL number: MFCD00007021
  • EINECS: 203-211-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Phenylpropyl aldehyde Structural

What is Phenylpropyl aldehyde?

Chemical properties

Pale Yellow Oil

Chemical properties

Phenylpropyl aldehyde occurs in Sri Lanka cinnamon bark oil, among others. The aldehyde is a colorless liquid with a strong, floral, slightly balsamic, heavy hyacinth-like odor. It tends to undergo self-condensation. Dihydrocinnamaldehyde can be obtained with scarcely any byproducts by selective hydrogenation of cinnamaldehyde. It is used in perfumery for hyacinth and lilac compositions.

Chemical properties

3-Phenylpropionaldehyde has a strong, pungent, floral odor reminiscent of hyacinth with a balsamic, green, warm (almost burning) flavor.

Occurrence

Reported found in the essential oil of Ceylon cinnamon and in strawberry. Also reported found in tomato, cinnamon, cassia leaf, Gruyere de Comte cheese, beer, cooked trassi, origanum (Spanish) and strawberry.

The Uses of Phenylpropyl aldehyde

3-Phenylpropanal (cas# 104-53-0) is a compound useful in organic synthesis.

Preparation

From phenyl propionitrile; also from cinnamic aldehyde diethylacetal.

Definition

ChEBI: 3-phenylpropanal is a benzene which is substituted by a 3-oxopropyl group at position 1. It has a role as a flavouring agent and a plant metabolite. It is an aldehyde and a member of benzenes. It is functionally related to a benzene.

Production Methods

Henylpropyl aldehyde is most commonly prepared by the partial hydrogenation of cinnamaldehyde. The 3-phenylpropanal that is formed during the hydroformylation of styrene can be separated from the isomeric 2-phenylpropanal as the bisulfite adduct. The Rosenmund reduction of dihydrocinnamoyl chloride in the presence of Pd/BaSO4 gives good yields of the aldehyde. The reaction of 2-propen-1-ol and phenylmercury chloride with CuCl2 and LiPdCl4 catalysts in methanol, and the reaction of phenyl bromide and allyl alcohol in the presence of PdCl2 and NaHCO3 in nonpolar solvents also lead to the formation of 3-phenylpropanal.

Taste threshold values

Taste characteristics at 20 ppm: green, melon, fruity and citrus.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 42, p. 1041, 1994 DOI: 10.1248/cpb.42.1041
Tetrahedron Letters, 35, p. 1275, 1994 DOI: 10.1016/0040-4039(94)88042-5

General Description

Hydrocinnamaldehyde is C=C double bond hydrogenated cinnamaldehyde. It has been synthesized by the selective hydrogenation of C=C double bond of cinnamaldehyde by various methods. Hydrocinnamaldehyde and nitromethane undergoes Henry reaction to form nitroaldols. The C1 and C3 position labelled with 13C of hydrocinnamaldehyde was subjected to mass spectrometry and the fragmentation pattern was elucidated.

Properties of Phenylpropyl aldehyde

Melting point: -42 °C
Boiling point: 97-98 °C/12 mmHg (lit.)
Density  1.019 g/mL at 25 °C (lit.)
vapor pressure  15 hPa (98 °C)
FEMA  2887 | 3-PHENYLPROPIONALDEHYDE
refractive index  n20/D 1.523(lit.)
Flash point: 203 °F
storage temp.  Store below +30°C.
solubility  0.74mg/l
form  Liquid
color  Clear colorless to light yellow
Odor at 10.00 % in dipropylene glycol. fresh cortex green leaf foliage balsam storax
Water Solubility  Miscible with chloroform, dichloromethane, ethyl acetate, alcohol and ether. Immiscible with water.
Sensitive  Air Sensitive
JECFA Number 645
BRN  1071910
CAS DataBase Reference 104-53-0(CAS DataBase Reference)
NIST Chemistry Reference 3-Phenylpropanal(104-53-0)
EPA Substance Registry System Benzenepropanal (104-53-0)

Safety information for Phenylpropyl aldehyde

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Phenylpropyl aldehyde

InChIKey YGCZTXZTJXYWCO-UHFFFAOYSA-N

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