基本情報
- CAS
1460-34-0- 標準SMILES
CCC(C)C(=O)C(=O)O- InChIKey
JVQYSWDUAOAHFM-UHFFFAOYSA-N- 分子式
- C6H10O3
- 平均分子量
- 130.14 g/mol
- 単同位体質量
- 130.06299418
概要
3-methyl-2-oxovaleric acid is a 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD). It has a role as a human 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 3-methyl-2-oxovalerate.
名称と識別子
- 優先名称
- alpha-Keto-beta-methylvaleric acid
- IUPAC
- 3-methyl-2-oxopentanoic acid
- 現地名
- 3-メチル-2-オキソ吉草酸
- 英語名
- 3-METHYL-2-OXOVALERIC ACID
- 分子式
- C6H10O3
- 分子量
- 130.14
名称と別名
3-Methyl-2-oxovaleric acid1460-34-0alpha-Keto-beta-methylvaleric acid2-OXO-3-METHYLVALERIC ACID2-Oxo-3-methylpentanoic acid3-Ethyl-3-methylpyruvic acid3-methyl-2-oxo-pentanoic acid2-oxo-3-methyl-n-valeric acid2-oxoisoleucine787T50HCIValpha-keto-beta-methyl-n-valeric acidCHEBI:35932
名称をさらに表示
3-メチル-2-オキソ吉草酸2-オキソ-3-メチル吉草酸α-ケト-β-メチル吉草酸3-メチル-2-オキソペンタン酸2-ケト-3-メチル吉草酸α-オキソ-β-メチル吉草酸2-オキソ-3-メチルペンタン酸α-ケト-3-メチル吉草酸2-オキソ-3-メチルバレリアン酸α-ケト-β-メチル-n-吉草酸3-METHYL-2-OXOPENTANOIC ACIDα-Keto-β-methylvaleric acidPentanoic acid, 3-methyl-2-oxo-3-METHYL-2-OXOVALERICMETHYLETHYLPYRUVIC ACID3-methyl-2-oxovalericaciα-Keto-3-methylvaleric acid
DTXSID508626702-keto-3-methylvaleric acidalpha-oxo-beta-methylvaleric acidalpha-oxo-beta-methyl-n-valeric acidKMVARefChem:503701DTXCID30203608FEMA NO. 3870, ACID-(A+-)-
データベース識別子
- CAS
1460-34-0、39748-49-7- PubChem CID
- 47
- DTXSID
DTXSID50862670- ChEBI
CHEBI:35932- UNII
- 787T50HCIV
- EC Number
- 215-955-0、254-616-1
- Nikkaji
- J39.560I
物性
構造計算による物性
- XLogP
- 1.1
- 極性表面積
- 54.4 Ų
- 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
- 128
実験および物理化学的性質
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water
Soluble (in ethanol)
Boiling Point233 °C
Physical DescriptionWhite crystalline powder; slight fruity aroma
Collision Cross Section
127.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
127.3 Ų [M-H]-
物理化学的性質
- 融点
- 42 °C · 42°C
- 沸点
- 84 °C · 84 °C / 18mmHg
- 比重(密度)
- 1.087 · 1.087±0.06 g/cm3(Predicted)
- FEMA
- 3870 · 3870 | 3-METHYL-2-OXOPENTANOIC ACID
- 貯蔵温度
- Refrigerator
- 溶解性
- 130 mg/mL · DMSO : 130 mg/mL (998.92 mM)
- 酸解離定数(Pka)
- 2.65 · 2.65±0.54(Predicted)
- 外見
- powder to crystal
- 色
- White to Light yellow
- JECFA Number
- 632 · 632
- InChI
- 1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
- InChIKey
- JVQYSWDUAOAHFM-UHFFFAOYSA-N
- SMILES
- CC(C(C(O)=O)=O)CC
- LogP
- 0.17 · 0.17
- CAS データベース
- 1460 · 1460-34-0(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。
GHS分類
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Informationalpha-Keto-beta-methylvaleric acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesEye Irrit. 2A (100%)
毒性情報
Health EffectsChronically high levels of 3-methyl-2-oxovaleric acid are associated with Maple Syrup Urine Disease.
Toxicity Summary
3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1, whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-methyl-1-hydroxybutyl-ThPP. It is used as a clinical marker for maple syrup urine disease (MSUD). MSUD is caused by a deficiency of the branched-chain -keto acid dehydrogenase complex resulting in an accumulation of branched-chain amino acids and the corresponding -keto-and -hydroxy acids in blood, urine and cerebrospinal fluid causing neurological damage and mental retardation.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- wgk
- WGK 3
- hs_code
- 2918300090
- risk_code
- 36/37/38-36
- 化審法
- (2)-1503
- hazard_code
- Xi
- safety_code
- 26-36/37/39-36
- Hazard Classifications
- Eye Irrit. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
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
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
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補足説明
定義ChEBI: A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD).
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