FComEx: Hexanal (PC000912)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:22 UTC

Update date

2017-01-19 02:36:41 UTC

FoodComEx ID

PC000912

FoodDB Record

FDB008068

Chemical Information

Name

Hexanal

Description

Hexanal, 1-hexanal, n-hexanal, is also known as caproaldehyde or hexanaldehyde. It belongs to the class of organic compounds known as medium-chain aldehydes which have a chain length between 6 and 12 carbon atoms and therefore is considered a fatty aldehyde lipid molecule. Hexanal is a very hydrophobic molecule that is relatively neutral. It is a colorless clear liquid. It has a fresh green, fatty or grassy scent with a green, fatty, leafy or aldehydic taste. Hexanal exists in all eukaryotes, from yeast to humans. Different foods contain hexanal with the highest concentrations found in black walnuts, corns, and tea and with lower concentrations in common grapes, thornless blackberries, and tortilla. Hexanal has also been detected in palms, mentha (mint), wax gourds, grapes, and kiwis making hexanal a potential biomarker for the consumption of these foods. Hexanal has been used to increase post-harvest longevity and color of certain fruits ( https://doi.org/10.1016/B978-0-12-809807-3.00009-3). Hexanal was also detected in humans breastmilk samples. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal, together with higher levels of 2-hydroxyhexanal and 4-hydroxynonena, are associated with poorer patient prognosis (PMID: 17487452). Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group because its concentrations in uremic patients were found to exceed the normal general population concentrations (PMID: 22626821). Hexanal is a volatile compound that has been associated with the development of undesirable flavours and has been proposed as a potential marker of milk quality. Hexanal, a major breakdown product of linoleic acid (LA, n ‚Äì 6, an polyunsaturated fatty acid, PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products such as baby formulae and was correlated with the hexanal concentration (https://doi.org/10.1016/j.foodchem.2007.08.042).

CAS Number

66-25-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Hexanal	biospider
Caproaldehyde	db_source
Caproic aldehyde	db_source
Capronaldehyde	biospider
FEMA 2557	db_source
Hexaldehyde	biospider
Hexanaldehyde	biospider
Hexoic aldehyde	biospider
Hexyl aldehyde	biospider
Hexylaldehyde	biospider
N-caproaldehyde	biospider
N-caproic aldehyde	biospider
N-capronaldehyde	biospider
N-caproylaldehyde	biospider
N-hexaldehyde	biospider
N-hexanal	biospider
N-hexylaldehyde	biospider

Chemical Formula

C6H12O

IUPAC name

hexanal

InChI Identifier

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3

InChI Key

JARKCYVAAOWBJS-UHFFFAOYSA-N

Isomeric SMILES

CCCCCC=O

Average Molecular Weight

100.1589

Monoisotopic Molecular Weight

100.088815006

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents