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4-Hydroxyoctenal

HCID 5283334
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
17449-15-9
Standard SMILES
CCCCC(O)/C=C/C=O
InChIKey
PYWFGGNTBVBZAT-GQCTYLIASA-N
Molecular formula
C8H14O2
Average molar mass
142.2 g/mol
Monoisotopic mass
142.09937969

Overview

4-hydroxy-2-octenal is a monounsaturated fatty aldehyde.

Names & identifiers

Preferred name
4-Hydroxyoctenal
IUPAC
(E)-4-hydroxyoct-2-enal

Names & synonyms

4-Hydroxyoctenal2-OCTENAL, 4-HYDROXY-(E)-4-hydroxyoct-2-enal(E)-4-Hydroxy-2-octenal55-88-92-Octenal, 4-hydroxy-, (E)-(E)-isomer of 4-hydroxy-2-octenalOctenal, 4-hydroxy-(2E)-4-Hydroxyoct-2-enalSCHEMBL4944801FAL 8:1;OCHEBI:180298
Show more names
DTXSID601018931LMFA0600003973529-62-1

Database identifiers

CAS
17449-15-9、55-88-9、73529-62-1
PubChem CID
5283334
DTXSID
DTXSID601018931
ChEBI
CHEBI:180298
Nikkaji
J2.301.187E、J49.915C

Properties

Computed structural properties

XLogP
1.1
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
10
Formal charge
0
Complexity
108

Experimental & physicochemical properties

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

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-Hydroxyoctenal 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.

Uses & manufacturing

UsesNaturally produced by the body (endogenous).

Related reactions

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Compound notes

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