( Z ) -3-hexenal

Structural formula
General
Surname	( Z ) -3-hexenal
other names	cis -3-hexenal; ( Z ) -hex-3-enal; ( Z ) -3-hexene-1-al;
Molecular formula	C 6 H 10 O
Brief description	colorless liquid with a green, fruity odor
External identifiers / databases
EC number	229-854-4
ECHA InfoCard	100.027.141
PubChem	643941
Wikidata	Q158587
properties
Molar mass	98.14 g mol −1
Physical state	liquid
density	0.976 g cm −3 (25 ° C)
boiling point	20 ° C (0.3 hPa )
solubility	slightly soluble in water
Refractive index	1.44 (20 ° C)
safety instructions
H and P phrases	H: 226-319
	P: 210-305 + 351 + 338-370 + 378
	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

( Z ) -3-Hexenal is a chemical compound from the group of aldehydes .

Occurrence

Strawberry "Mieze Schindler".

( Z ) -3-Hexenal occurs in nature in a variety of ways (e.g. in spinach, peaches, citrus fruits, strawberries, green tea, basil, parsley) and belongs to the group of green leaf fragrances . Many of these substances are biosynthesized from α-linolenic acid , which is split by means of lipoxygenases via a peroxycarboxylic acid to form volatile ( Z ) -3-hexenal and a non-volatile C ₁₂ compound. The 3-hexenal is reduced to the most famous representative of the green leaf fragrances , the ( Z ) -3-hexenol , which is also known as leaf alcohol . The isomer ( E ) -3-hexenal also occurs naturally (e.g. in sugar melons, tea, apples and apricots). However, its aroma is significantly weaker than that of the ( Z ) isomer.

It is also produced when foods containing linoleic acid are stored .

Extraction and presentation

( Z ) -3-Hexenal can be obtained by oxidation of ( Z ) -3-Hexenol .

properties

( Z ) -3-Hexenal is a colorless liquid with a green, fruity odor. The technical product is offered as a solution in triacetin .

use

( Z ) -3-Hexenal is an important component of the aroma of freshly squeezed juices (e.g. orange, grapefruit). Since it is much more unstable than ( E ) -2-hexenal (to which it isomerizes), it is rarely used to flavor foods.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet cis-3-Hexenal solution, 50% in triacetin, stabilzed from Sigma-Aldrich , accessed on July 21, 2019 ( PDF ).
↑ Stefan Schwab: Leaf fragrance samples of various host tree species of the horse chestnut leaf miner (Cameraria ohridella DESCHKA & DIMIĆ 1986). (PDF; 10.8 MB) Dissertation at the Friedrich-Alexander-University Erlangen-Nürnberg , 2008.
↑ Waldemar Ternes: Scientific basics of food preparation . Behr's, 2008, ISBN 978-3-89947-422-0 , pp. 315 ( limited preview in Google Book search).
↑ ^a ^b Hans-Dieter Belitz, Werner Grosch, Peter Schieberle: Textbook of food chemistry . Springer, 2001, ISBN 3-540-41096-1 , pp. 194, 390, 616, 818 ( limited preview in Google Book search).
↑ Andrea Büttner: Important aromas in freshly squeezed citrus fruit juices from different orange varieties . Herbert Utz Verlag, 1999, ISBN 978-3-89675-523-0 , p. 141 ( limited preview in Google Book search).
↑ Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 84 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet cis-3-Hexenal solution, 50% in triacetin, stabilzed from Sigma-Aldrich , accessed on July 21, 2019 ( PDF ).

[2] Stefan Schwab: Leaf fragrance samples of various host tree species of the horse chestnut leaf miner (Cameraria ohridella DESCHKA & DIMIĆ 1986). (PDF; 10.8 MB) Dissertation at the Friedrich-Alexander-University Erlangen-Nürnberg , 2008.

[buch1-3] Waldemar Ternes: Scientific basics of food preparation . Behr's, 2008, ISBN 978-3-89947-422-0 , pp. 315 ( limited preview in Google Book search).

[Lebensmittelchemie-4] Hans-Dieter Belitz, Werner Grosch, Peter Schieberle: Textbook of food chemistry . Springer, 2001, ISBN 3-540-41096-1 , pp. 194, 390, 616, 818 ( limited preview in Google Book search).

[buch2-5] Andrea Büttner: Important aromas in freshly squeezed citrus fruit juices from different orange varieties . Herbert Utz Verlag, 1999, ISBN 978-3-89675-523-0 , p. 141 ( limited preview in Google Book search).

[Legrum-6] Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 84 ( limited preview in Google Book search).