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4-Hydroxynonenal

HCID 5283344
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
128946-65-6
標準SMILES
CCCCCC(O)/C=C/C=O
InChIKey
JVJFIQYAHPMBBX-FNORWQNLSA-N
分子式
C9H16O2
平均分子量
156.22 g/mol
単同位体質量
156.11502975

概要

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.

名称と識別子

優先名称
4-Hydroxynonenal
IUPAC
(E)-4-hydroxynon-2-enal
英語名
HNE
分子式
C9H16O2
分子量
156.22

名称と別名

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
名称をさらに表示
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-

データベース識別子

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

物性

構造計算による物性

XLogP
1.7
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
6
重原子数
11
形式電荷
0
複雑度
119

実験および物理化学的性質

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

物理化学的性質

沸点
125 · 125-127 °C(Press: 2 Torr)
比重(密度)
0.941 · 0.941±0.06 g/cm3(Predicted)
貯蔵温度
-70 °C · -70°C
溶解性
50 mg/ml; · DMF: >50 mg/ml; DMSO: >50 mg/ml; Ethanol: >50 mg/ml; PBS pH 7.2: >1 mg/ml
酸解離定数(Pka)
13.31 · 13.31±0.20(Predicted)
外見
無色油。
色
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 データベース
75899 · 75899-68-2(CAS DataBase Reference)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

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 件

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 件

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

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 件

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

用途と製造

UsesNaturally produced by the body (endogenous).
応用分野 · 1 件

使用HNE 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]

上流・下流製品情報

上流原料

2,3-EPOXYOCTANAL2-Nonen-4-ol, 1-bromo-, (2E)-2-Nonenal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2E)-

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

安全データ

wgk
WGK 3
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2
ストレージクラス
3 - Flammable liquids
(E)-4-hydroxynon-2-enal dimethyl acetal
メトキシメチレントリフェニルホスホラン
1-オクテン-3-オール
ペンチルマグネシウムブロミド (18%テトラヒドロフラン溶液, 約1mol/L)
アクロレイン (モノマー)
ヘキサナール
1-ブロモペンタン

下流製品

4-HYDROXY NONENAL MERCAPTURIC ACID

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