Phenylpropyl aldehyde Property

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

Odor Type

green

Water Solubility 

Miscible with chloroform, dichloromethane, ethyl acetate, alcohol and ether. Immiscible with water.

Sensitive 

Air Sensitive

JECFA Number

645

BRN 

1071910

InChIKey

YGCZTXZTJXYWCO-UHFFFAOYSA-N

LogP

2.04

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

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

2

RTECS 

MW4890000

F 

10-23

Autoignition Temperature

245 °C DIN 51794

TSCA 

Yes

HS Code 

29122900

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Phenylpropyl aldehyde Chemical Properties,Usage,Production

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.

Uses

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

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.

Preparation

From phenyl propionitrile; also from cinnamic aldehyde diethylacetal.

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.