Phenylethanal

Structural formula
General
Surname	Phenylacetaldehyde
other names	Phenylethanal; Hyacinthin; alpha-tolualdehyde; α-tolualdehyde;
Molecular formula	C 8 H 8 O
Brief description	colorless liquid with a pleasant odor
External identifiers / databases
EC number	204-574-5
ECHA InfoCard	100.004.159
PubChem	998
DrugBank	DB02178
Wikidata	Q424998
properties
Molar mass	120.15 g · mol -1
Physical state	liquid
density	1.03 g cm −3
Melting point	−10 ° C
boiling point	195 ° C
Vapor pressure	35 Pa (19 ° C)
solubility	difficult in water (2.2 g · l -1 at 25 ° C); soluble in ethanol and ether ; insoluble in glycerin ;
Refractive index	1.524–1.528 (at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-317
	P: 280-302 + 352
Toxicological data	1550 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

blackberry

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 .

[GESTIS-1] ↑ ^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) .

[merck_index-2] Susan Budavari (Ed.): The Merck Index . 12th edition. Merck & Co., Whitehouse Station, New Jersey, USA 1996, ISBN 0-911910-12-3 .

[good_scents-3] Datasheet Phenylacetaldehyde at The Good Scents Company , July 25, 2008.

[4] 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 .

[5] 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.

[6] 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 .

[7] Walter Kuhn (Haarmann & Reimer GmbH): Method for stabilizing phenylacetaldehyde , Patent WO / 2002/046135 (2002). - [1]

[qia-aina-8] Yancheng Chaina Fragrance: Natural Hyacinthin ( Memento from June 30, 2013 in the web archive archive.today ).

[9] ER Pavillard; EA Wright: An antibiotic from maggots , in: Nature , 1957 , 180 , pp. 916-917; doi: 10.1038 / 180916b0 .

[10] 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.

[11] Tobacco ingredients in PMI products for sale made in Germany. In: Homepage Philip Morris. Retrieved January 16, 2018 .

[12] Pherobase.com: Semiochemical - 2-phenylacetaldehyde .