Phenylethanal
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Phenylacetaldehyde | ||||||||||||||||||
other names |
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Molecular formula | C 8 H 8 O | ||||||||||||||||||
Brief description |
colorless liquid with a pleasant odor |
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External identifiers / databases | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 120.15 g · mol -1 | ||||||||||||||||||
Physical state |
liquid |
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density |
1.03 g cm −3 |
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Melting point |
−10 ° C |
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boiling point |
195 ° C |
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Vapor pressure |
35 Pa (19 ° C) |
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solubility | |||||||||||||||||||
Refractive index |
1.524–1.528 (at 20 ° C) |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Phenylacetaldehyde or phenylethanal is a naturally occurring aromatic compound from the group of aldehydes .
Occurrence
Phenylacetaldehyde is found in buckwheat ( Fagopyrum esculentum ), chocolate, and many other foods. This substance is also found as an odorous substance in a large number of plants, including apples , blackberries , potatoes , melons , peaches , tamarinds and tomatoes . It occurs in particularly high concentrations in Brazilian flower oil from Lecythis usitata var. Paraensis (28.20%), in Mori flower oil from Eschweilera coriacea (2.40%) and in chicory extract (1.04%).
Extraction and presentation
Phenylacetaldehyde can be obtained by acid-catalyzed isomerization of styrene oxide or oxidation of 2-phenylethanol with chromic acid .
properties
Because of its reactivity as an aldehyde, phenylacetaldehyde polymerizes when standing in air and becomes more viscous. The self-condensation mainly forms 2,4,6-tribenzyl-1,3,5-trioxane.
The flash point is 87 ° C.
The smell is described as honey-sweet, hyacinth-like, green and cocoa-like, also as orange-like, rose-like.
Among other substances, phenylacetaldehyde is a carrier of the antibiotic effect of maggot therapy .
use
Phenylacetaldehyde is used industrially in perfume production, including as a tobacco additive to improve the aroma of cigarettes. The amino acid phenylalanine can be produced from phenylacetaldehyde by means of Strecker synthesis .
physiology
Many insects ( butterflies , hymenoptera , beetles and netwings ) use this aldehyde for chemical communication ( pheromone ).
Individual evidence
- ↑ a b c d e f g h i Entry on phenylacetaldehyde in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
- ↑ a b c Susan Budavari (Ed.): The Merck Index . 12th edition. Merck & Co., Whitehouse Station, New Jersey, USA 1996, ISBN 0-911910-12-3 .
- ↑ a b c d e Datasheet Phenylacetaldehyde at The Good Scents Company , July 25, 2008.
- ↑ D. Janes; D. Kantar; S. Kreft; H. Prosen: Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS , in: Food Chemistry , 2009 , 112 , pp. 120-124; doi: 10.1016 / j.foodchem.2008.05.048 .
- ↑ P. Schnermann, P. Schieberle: Evaluation of key odorants in milk chocolate and cocoa cass by aroma extract dilution analyzes , in: J. Agric. Food Chem. , 1997 , 45 , pp. 867-872.
- ↑ I. Salla; O. Bergada; P. Salagre; Y. Cesteros; F. Medina; JE Sueiras; T. Montanari: Isomerization of styrene oxide to phenylacetaldehyde by fluorinated mordenites using microwaves , in: Journal of Catalysis , 2005 , 232 , pp. 239–245; doi: 10.1016 / j.jcat.2004.10.011 .
- ^ Walter Kuhn (Haarmann & Reimer GmbH): Method for stabilizing phenylacetaldehyde , Patent WO / 2002/046135 (2002). - [1]
- ↑ Yancheng Chaina Fragrance: Natural Hyacinthin ( Memento from June 30, 2013 in the web archive archive.today ).
- ↑ ER Pavillard; EA Wright: An antibiotic from maggots , in: Nature , 1957 , 180 , pp. 916-917; doi: 10.1038 / 180916b0 .
- ↑ GR Erdmann; SK Khalil: Isolation and identification of two antibacterial agents produced by a strain of Proteus mirabilis isolated from larvae of the screwworm (Cochliomyia hominivorax) (Diptera: Calliphoridae) , in: J. Med. Entomol. , 1986 , 23 , pp. 208-211.
- ↑ Tobacco ingredients in PMI products for sale made in Germany. In: Homepage Philip Morris. Retrieved January 16, 2018 .
- ↑ Pherobase.com: Semiochemical - 2-phenylacetaldehyde .