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4-Hydroxynonenal

HCID 5283344
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Basic information

CAS
128946-65-6
Standard SMILES
CCCCCC(O)/C=C/C=O
InChIKey
JVJFIQYAHPMBBX-FNORWQNLSA-N
Molecular formula
C9H16O2
Average molar mass
156.22 g/mol
Monoisotopic mass
156.11502975

Overview

4-hydroxynon-2-enal is an enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position. It has a role as a human metabolite. It is a 4-hydroxynonenal, a hydroxyaldehyde and an enal.

Names & identifiers

Preferred name
4-Hydroxynonenal
IUPAC
(E)-4-hydroxynon-2-enal
English name
HNE
Molecular formula
C9H16O2
Molecular weight
156.22

Names & synonyms

4-Hydroxynonenal75899-68-24-Hydroxy-2-nonenal4-HNE4-Hydroxy-2,3-nonenal(2E)-4-hydroxynon-2-enalK1CVM13F964-hydroxynonen-2-al4-HNE cpdRefChem:912599CHEBI:142593(E)-4-hydroxynon-2-enal
Show more names
HNECcris 17814-hydroxy-2-nonena(E)-4-HYDROXYNONENAL(±)4-Hydroxynon-2-enal4-HNE/4-Hydroxynonenal
trans-4-Hydroxy-2-nonenal(E)-4-hydroxy-2-nonenal(2E)-4-Hydroxy-2-nonenal128946-65-62-Nonenal, 4-hydroxy-, (2E)-4-hydroxy-2E-nonenalDTXSID40403952-NONENAL, 4-HYDROXY-

Database identifiers

CAS
128946-65-6、29343-52-0、75899-68-2
PubChem CID
5283344
DTXSID
DTXSID4040395
ChEMBL
CHEMBL454280
ChEBI
CHEBI:32585
UNII
K1CVM13F96
Nikkaji
J34.593H、J356.016C

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
6
Heavy atoms
11
Formal charge
0
Complexity
119

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty aldehydes [FA06]
Physical DescriptionSolid

Physicochemical properties

Boiling point
125 · 125-127 °C(Press: 2 Torr)
Density
0.941 · 0.941±0.06 g/cm3(Predicted)
storage temp.
-70 °C · -70°C
solubility
50 mg/ml; · DMF: >50 mg/ml; DMSO: >50 mg/ml; Ethanol: >50 mg/ml; PBS pH 7.2: >1 mg/ml
pka
13.31 · 13.31±0.20(Predicted)
form
Colorless oil.
color
Colorless to light yellow
InChI
InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
InChIKey
JVJFIQYAHPMBBX-FNORWQNLSA-N
SMILES
C(=O)/C=C/C(O)CCCCC
CAS DataBase Reference
75899 · 75899-68-2(CAS DataBase Reference)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as 4-Hydroxynonenal 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) (A7868). 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 (A7869).

Signs and Symptoms · 1 item

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.

Chemistry & industry

Pharmacology

Metabolism/MetabolitesUremic 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.
MeSH Pharmacological Classification · 2 items

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.

Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES.

Cellular LocationsExtracellular

Uses & manufacturing

UsesNaturally produced by the body (endogenous).
Applications · 2 items

Uses4-Hydroxynonenal is an irreversible inhibitor of Na+/K+-ATPase activity.

UsesHNE is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid. 4-hydroxy Nonenal is widely used as a marker of lipid peroxidation. It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity. HNE inhibits pro-oxidant-induced Ca2+ release from mitochondria at 10-50 μM.[Cayman Chemical]

Upstream & downstream products

Upstream raw materials

2,3-EPOXYOCTANAL2-Nonen-4-ol, 1-bromo-, (2E)-

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
FDA UNII
1 CVM13F96 · K1CVM13F96
UNSPSC Code
12352114 · 12352114
NACRES
77 · NA.77
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Danger
Hazard statements
225 · H225-H319
Precautionary statements
210 · P210-P233-P240-P241-P242-P305+P351+P338
WGK Germany
3 · WGK 3
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
2 Flam · Eye Irrit. 2Flam. Liq. 2
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
WGK 3
Signal word
Danger
Symbol(GHS)
GHS02,GHS07
Storage Class
3 - Flammable liquids
Hazard statements
H225-H319
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2
Precautionary statements
P210-P233-P240-P241-P242-P305+P351+P338
2-Nonenal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2E)-
(E)-4-hydroxynon-2-enal dimethyl acetal
Methoxymethylenetriphenylphosphorane
1-Octen-3-ol
N-PENTYLMAGNESIUM BROMIDE
Acrolein
Hexanal
1-Bromopentane

Downstream products

4-HYDROXY NONENAL MERCAPTURIC ACID

Additional notes

DefinitionChEBI: 4-hydroxynon-2-enal is an enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position. It has a role as a human metabolite. It is a hydroxyaldehyde, an enal and a 4-hydroxynonenal.