ContaminantDB: Hexanal

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:50:30 UTC

Update Date

2026-04-17 18:17:30 UTC

Accession Number

CHEM003141

Identification

Common Name

Hexanal

Class

Small Molecule

Description

Hexanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Hexanal is an alkyl aldehyde found in human biofluids. Human milk samples collected from women contains hexanal. 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 are associated with poorer patient prognosis. Hexanal is a volatile compound that has been associated with the development of undesirable flavours. The content of hexanal, which is a major breakdown product of linoleic acid (LA, n - 6 PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. A cardboard-like off-flavour is frequently associated with dehydrated milk products. This effect is highly correlated with the headspace concentration of hexanal. (4, 5).

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aldehyde
Food Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexanal	ChEBI
Aldehyde C-6	ChEBI
C6 Aldehyde	ChEBI
Caproaldehyde	ChEBI
Caproic aldehyde	ChEBI
Hexaldehyde	ChEBI
Hexan-1-al	ChEBI
Hexanaldehyde	ChEBI
Hexoic aldehyde	ChEBI
Hexylaldehyde	ChEBI
N-C5H11CHO	ChEBI
N-Caproaldehyde	ChEBI
N-Caproic aldehyde	ChEBI
N-Hexanal	ChEBI
N-Hexylaldehyde	ChEBI
Capronaldehyde	HMDB
Hexanal	MeSH
n-Capronaldehyde	HMDB

Chemical Formula

C₆H₁₂O

Average Molecular Mass

100.159 g/mol

Monoisotopic Mass

100.089 g/mol

CAS Registry Number

66-25-1

IUPAC Name

hexanal

Traditional Name

hexanal

SMILES

CCCCCC=O

InChI Identifier

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

InChI Key

JARKCYVAAOWBJS-UHFFFAOYSA-N

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

Medium-chain aldehyde
Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000109 )
an <i>n</i>-alkanal (HEXANAL )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-56°C
Boiling Point	Not Available
Solubility	5.64 mg/mL at 30°C

Predicted Properties

Property	Value	Source
Water Solubility	4.49 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.65	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.15 m³·mol⁻¹	ChemAxon
Polarizability	12.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-65f52440a5d20229be6c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-89f4d5edf8639a778ef4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-98fd24ab2b6d3d9cf3cf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-65f52440a5d20229be6c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-89f4d5edf8639a778ef4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-98fd24ab2b6d3d9cf3cf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-f6f6f2d2922256923f62	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0089-9200000000-a864c6ae8f499374570f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00lr-9000000000-c35aa664e0abaa7ff754	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-00lr-9100000000-32a2d24a74c86ead890b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-65f52440a5d20229be6c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-13ae9f72ffb8573eac28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-e06f68e7ce93f5ced938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4900000000-3680e8fedab54e7572cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-9400000000-d3150dfd70fdee4bfc78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-c161db43b692fc558533	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-16f962506c9316343166	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-1fd34894f517ecf1f19a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-054aa18a9a05fa35cf01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-658fe53778817eb82301	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-b0e3f2f55178b8aacda1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c5c7ace495de00bff008	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a5c-9000000000-d214e2877cddafdcb757	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-f2f5a7e46a17ef9b2c6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-7d79b3949754c5802624	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-72ae5d9e7cc61abeff7f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as hexanal are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3).

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0005994

FooDB ID

FDB008068

Phenol Explorer ID