4-Methyl-2-oxovaleric acid (HCID 70)

概要

4-methyl-2-oxopentanoic acid is a 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease. It has a role as a human metabolite and an algal metabolite. It is a branched-chain keto acid and a 2-oxo monocarboxylic acid. It is functionally related to a valeric acid. It is a conjugate acid of a 4-methyl-2-oxopentanoate.

名称と識別子

優先名称: 4-Methyl-2-oxovaleric acid
IUPAC: 4-methyl-2-oxopentanoic acid
現地名: 4-メチル-2-オキソ吉草酸
英語名: 4-Methyl-2-oxovaleric acid
分子式: C6H10O3
分子量: 130.14

名称と別名

4-methyl-2-oxopentanoic acid816-66-04-Methyl-2-oxovaleric acidalpha-Ketoisocaproic acid2-OXO-4-METHYLPENTANOIC ACID2-Oxoisocaproate2-Oxoisocaproic acid4-methyl-2-oxopentanoatePentanoic acid, 4-methyl-2-oxo-alpha-oxoisocaproate2-Oxo-4-methylvaleric acid2-Oxoleucine

名称をさらに表示

4-メチル-2-オキソ吉草酸2-オキソイソヘキサン酸2-オキソイソカプロン酸4-メチル-2-オキソペンタン酸α-オキソ-α-デアミノロイシン2-オキソ-4-メチルペンタン酸2-オキソ-4-メチル吉草酸α-ケトイソカプロン酸ケトロイシンα-ケト-4-メチルペンタン酸2-オキソ-4-メチルバレリアン酸2-ケト-4-メチルペンタン酸KETOLEUCINEALPHA KETOISOCAPROATE2-keto-isocaproateALPHA-KETOLEUCINEMethyl-2-oxovalericIsopropylpyruvicacid

2-ketoisocaproate2-oxo-4-methylpentanoatealpha-keto-isocaproic acid2-keto-4-Methylvaleric acid4GUJ8AH400DTXSID6061157CHEBI:48430CHEBI:17865

データベース識別子

CAS: 816-66-0
PubChem CID: 70
DTXSID: DTXSID6061157
ChEMBL: CHEMBL445647
ChEBI: CHEBI:48430
UNII: 4GUJ8AH400
EC Number: 212-435-5
Nikkaji: J39.557I

物性

構造計算による物性

XLogP: 0.9
極性表面積: 54.4 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 3
重原子数: 9
形式電荷: 0
複雑度: 126

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.053-1.058

Flavoring AgentsEU Flavoring substances

Solubility · 3 件

32 mg/mL

Soluble in water

Soluble (in ethanol)

Boiling Point251 °C

物理化学的性質

融点: 8 · 8-10 °C
沸点: 82 · 82-83 °C11 mm Hg(lit.)
比重(密度): 1.055 g/mL · 1.055 g/mL at 20 °C(lit.)
屈折率: 20 · n20/D 1.431
FEMA: 3871 · 3871 | 4-METHYL-2-OXOPENTANOIC ACID
貯蔵温度: 2 · 2-8°C
溶解性: 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml
酸解離定数(Pka): 2.65 · 2.65±0.54(Predicted)
外見: clear liquid
色: Colorless to Yellow
臭い (Odor): フルーティーな
においのタイプ: フルーティーな
水溶解度: 水に溶ける。
JECFA Number: 633 · 633
BRN: 1701823 · 1701823
InChI: 1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChIKey: BKAJNAXTPSGJCU-UHFFFAOYSA-N
SMILES: CC(C)CC(=O)C(O)=O
LogP: 0.17 · 0.17
CAS データベース: 816 · 816-66-0(CAS DataBase Reference)
NISTの化学物質情報: 4 · 4-Methyl-2-oxovaleric acid(816-66-0)
EPAの化学物質情報: .alpha.-Ketoisocaproic acid (816-66-0)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationPentanoic acid, 4-methyl-2-oxo-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Corr. 1C (100%)

毒性情報

Health EffectsChronically high levels of keto-leucine are associated with Maple Syrup Urine Disease.

Toxicity SummaryKetoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain.

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

安全データ

F: 3-9-13
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 3
hs_code: 2918.30.9000
risk_code: 34
消防法: 危-4-3-III
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
packing_group: III
Hazard Classifications: Skin Corr. 1B
ストレージクラス: 8A - Combustible corrosive hazardous materials

化学と産業

薬理情報

Tissue LocationsNeuron

Cellular LocationsCytoplasm

Metabolite Pathways2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency

用途と製造

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Use Classification · 3 件

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationPentanoic acid, 4-methyl-2-oxo-: ACTIVE

応用分野

天然物の起源Reported found in banana, asparagus, cheese, white wine, cocoa, blue cheese and provolone cheese.

使用4-Methyl-2-oxovaleric acid is an intermediate in the metabolism of leucine and also used as flavoring agents.

上流・下流製品情報

上流原料

L-ロイシン

下流製品

4-メチル-2-オキソペンタン酸メチル (R)-2-ヒドロキシ-4-メチルペンタン酸 L-ロイシン酸

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補足説明

定義ChEBI: A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.