| Description | 2-phenylpropionaldehyde is also known as 2-phenylpropanal. It belongs to the family of phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 2- phenylpropionaldehyde is a naturally occurring compound in various foods including roasted nuts, cooked potatoes, cheese, wine, fruit, vegetables, coffee, tea, and cocoa. 2-phenylpropionaldehyde is used as a flavoring agent. Once absorbed, 2-phenylpropionaldehyde can be converted to phenyl-substituted carboxylic acids, which can be conjugated with glucuronic acid and excreted in the urine. 2-phenylpropionaldehyde can also undergo β- oxidation to benzoic acid or phenylacetic acid derivatives, which are conjugated with glycine or glutamine before being excreted in the urine.
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| References | [1] WHO Food Additives Series: 54, Safety evaluation of certain food additives
[2] https://webgate.ec.europa.eu
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| Chemical Properties | clear colorless liquid |
| Chemical Properties | 2-PHENYLPROPIONALDEHYDE identified in dried
mushroom, is a colorless liquid with a green hyacinth odor. Hydratropaldehyde
can be hydrogenated to hydratropic alcohol, which is also used to a limited extent by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of
catalysts. The product is used in perfumes for, for example, household products. |
| Chemical Properties | 2-Phenylpropionaldehyde has an intense, green, floral odor reminiscent of hyacinth. |
| Occurrence | Reported found in microbially fermented tea and some varieties of mushrooms. |
| Uses | 2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625). |
| Definition | ChEBI: 2-phenylpropanal is a member of the class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group. The major species at pH 7.3. |
| Preparation | By alkaline condensation of acetophenone and ethyl chloroacetate; also by distillation of methylphenyl ethylene glycol in
91% yields (under atmospheric pressure). |
| Synthesis Reference(s) | Journal of the American Chemical Society, 97, p. 5608, 1975 DOI: 10.1021/ja00852a062
Organic Syntheses, Coll. Vol. 3, p. 733, 1955
Tetrahedron Letters, 15, p. 3059, 1974 |
| General Description | 2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor. |
| Flammability and Explosibility | Nonflammable |
| Trade name | Floralozone (IFF), Florazon (Symrise). |
| Safety Profile | : Moderately toxic by
ingestion. Combustible liquid. When heated
to decomposition it emits acrid smoke and
irritating fumes. See also ALDEHYDES. |
| Purification Methods | It may contain up to 15% of acetophenone. Purify it via the bisulfite addition compound [Lodge & Heathcock J Am Chem Soc 109 3353 1987] and see Chapter 2 for preparation and decomposition of bisulfite adducts. [Beilstein 7 IV 695.] |
