3-ブロモピルビン酸
Bromopyruvic Acid
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基本情報
- CAS
1113-59-3- 標準SMILES
O=C(O)C(=O)CBr- InChIKey
PRRZDZJYSJLDBS-UHFFFAOYSA-N- 分子式
- C3H3BrO3
- 平均分子量
- 166.96 g/mol
- 単同位体質量
- 165.92655606
概要
3-bromopyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is replaced by bromine. Synthetic brominated derivative and structural analog of pyruvic acid. Highly reactive alkylating agent. Anti-cancer drug. It has a role as an alkylating agent and an antineoplastic agent. It is a 2-oxo monocarboxylic acid and an organobromine compound. It is functionally related to a pyruvic acid. It is a conjugate acid of a 3-bromopyruvate.
名称と識別子
- 優先名称
- Bromopyruvic Acid
- IUPAC
- 3-bromo-2-oxopropanoic acid
- 現地名
- 3-ブロモピルビン酸
- 英語名
- 3-Bromopyruvic acid
- 分子式
- C3H3BrO3
- 分子量
- 166.96
名称と別名
bromopyruvic acid3-bromopyruvic acid1113-59-33-bromo-2-oxopropanoic acidbromopyruvate3-Bromo-2-oxopropionic acid63JMV04GRKDTXSID7040940NSC-11731NSC-62343CHEBI:1314613-BrPA cpd
名称をさらに表示
3-ブロモピルビン酸2-オキソ-3-ブロモプロピオン酸ブロモピルビン酸3-ブロモ-2-オキソプロパン酸3-ブロモ-2-オキソプロピオン酸2-オキソ-3-ブロモプロパン酸2-Oxo-3-bromopropanoic acidbeta-bromopyruvicacidNSC 11731NSC 62343
RefChem:499406DTXCID5020940214-206-53-bromopyruvatePyruvic acid, bromo-Propanoic acid, 3-bromo-2-oxo-3-bromopyruvicacidMFCD00002587
データベース識別子
- CAS
1113-59-3- PubChem CID
- 70684
- DTXSID
DTXSID7040940- ChEMBL
CHEMBL177837- ChEBI
CHEBI:131461
物性
構造計算による物性補完中
- XLogP
- 0.5
- 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
- 2
- 重原子数
- 7
- 形式電荷
- 0
- 複雑度
- 98.4
物理化学的性質
- 融点
- 77 · 77-82 °C
- 沸点
- 223.4 · 223.4±23.0 °C(Predicted)
- 比重(密度)
- 1.7314 · 1.7314 (rough estimate)
- 屈折率
- 1.465 · 1.4650 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 1 g/10mL · 水：可溶1g/10mL 無色透明
- 外見
- 白色結晶性固体
- 酸解離定数(Pka)
- 1.84 · 1.84±0.54(Predicted)
- 色
- White to Almost white
- 水溶解度
- 水、ジメチルスルホキシド、酢酸エチル、水に溶ける。
- BRN
- 1746786 · 1746786
- InChI
- InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
- InChIKey
- PRRZDZJYSJLDBS-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C(=O)CBr
- CAS データベース
- 1113 · 1113-59-3(CAS DataBase Reference)
- EPAの化学物質情報
- 3 · Propanoic acid, 3-bromo-2-oxo- (1113-59-3)
化学的性質
化学的特性Off-white solid
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
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 48 reports by companies from 6 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesSkin Corr. 1B (100%)
安全データ
- F
- 19-21
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UZ0840000
- ridadr
- UN 3261 8/PG 2
- hs_code
- 2918300090
- risk_code
- 34-20/21/22
- hazard_code
- C
- hazard_note
- Corrosive
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- packing_group
- II
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
化学と産業
薬理情報
MeSH Pharmacological Classification
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
用途と製造
General Manufacturing InformationPropanoic acid, 3-bromo-2-oxo-: ACTIVE
応用分野
使用Bromopyruvic Acid is a synthetic brominated derivative of pyruvic acid. Bromopyruvic Acid maybe a potential treatment for certain types of cancer as it has shown to be effective at eliminating aggress ive liver tumors.
一般的な説明Bromopyruvic acid is an affinity label for cysteine residues. It acts as cross-linker between nucleic acids and proteins. Kinetics of inactivation of pancreatic ribonuclease A by bromopyruvic acid has been investigated.
調製方法
製造方法Synthesis method of 3-bromopyruvic acid: add a little concentrated sulfuric acid and solvent dichloromethane to pyruvic acid in a reaction flask, add bromine dropwise for about 3.5h and stir, a white precipitate is produced, then continue to stir for 1h, dilute with cyclohexane and petroleum ether, then cool the reaction mixture to get crystals, filter, wash with petroleum ether and dry to get the finished product of 3-bromopyruvic acid.
純化方法Dry it by azeotropic distillation (with toluene), and then recrystallise it from dry CHCl3. Dry for 48hours at 20o (0.5 torr) over P2O5. Store it at 0o. [Labandiniere et al. J Org Chem 52 157 1987, Beilstein 3 III 1167.]
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