(2S)-2-hydroxybutanedioic acid

• ChemBase编号: 102583
• 分子式: C4H6O5
• 平均质量: 134.08744
• 单一同位素质量: 134.02152329
• SMILES: O[C@@H](CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@@H](C(=O)O)O
• InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
• InChIKey: BJEPYKJPYRNKOW-REOHCLBHSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-hydroxybutanedioic acid
• IUPAC传统名: (-)-malic acid
• 别名: (S)-(-)-2-羟基琥珀酸; L-羟基丁二酸; L-苹果酸; L-(-)-苹果酸; (S)-2-hydroxysuccinic acid; (2S)-2-hydroxybutanedioic acid; (2S)-2-Hydroxybutanedioic Acid; (-)-(S)-Malic Acid; (-)-Hydroxysuccinic Acid; (-)-L-Malic Acid; (-)-Malic Acid; (2S)-2-Hydroxy-succinic Acid; (2S)-Malic Acid; (S)-Malic Acid; Apple Acid; L-(-)-Malic Acid; L-Apple Acid; L-Malic Acid; NSC 9232; S-(-)-Malic Acid; S-2-Hydroxybutanedioic Acid; L-(-)-Malic Acid; L-Hydroxysuccinic acid; L-Hydroxybutanedioic acid; L-MALIC ACID FREE ACID; L-(-)-Malic acid; L-MALIC ACID; L-MALIC ACID, α20D-23.5(C=5.6 PYRIDINE); (S)-(-)-2-Hydroxysuccinic acid; (S)-(-)-Hydroxysuccinic acid; (S)-(-)-Hydrosuccinic acid

登记号

• CAS号: 97-67-6
• EC号: 202-601-5
• MDL号: MFCD00064213; MFCD00063990
• Beilstein号: 1723541
• 默克索引号: 145707
• PubChem SID: 162089277; 24897010; 24845248; 24897161; 24847101; 24896463
• PubChem CID: 222656

理论计算性质

• Acid pKa: 3.198357
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -3.9168313
• LogD (pH = 7.4): -6.814561
• Log P: -1.1136414
• 摩尔折射率: 24.8752 cm^3
• 极化性: 10.123206 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble0.5 M at 20 °C, clear, colorless; Soluble in acetone, dioxane, water, methanol and ethanol. Insoluble in benzene
• 熔点: 100-106°C; 101 - 103°C; 101-103 °C(lit.); 101-107°C; 103-106 °C
• 闪点: 220°C(428°F)
• 密度: 1.60
• 比旋光度: [α]20/D -27°, c = 5.5 in pyridine; [α]20/D -30±2°, c = 5.5% in pyridine; -27 (c=5.5 in pyridine)
• 疏水性(logP): -1.52
• pKa: (1) 3.46, (2) 5.10

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: ON7175000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26; 26-37-60
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥95%; ≥99%; ≥99.0%; ≥99.0% (T); 95%; 95-100% (enzymatic); 97%; 99%
• 级别: purum; ReagentPlus®; SAJ special grade
• 光学纯度: ee: 99% (GLC)
• 适用性: suitable for cell culture; suitable for insect cell culture
• 燃烧残渣: ≤0.1% (as SO4)
• 杂质: ≤0.01% Phosphorus (P); ≤0.1% Insoluble matter; ≤0.3% water
• 痕量阳离子: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; Fe: ≤10 mg/kg; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• 痕量阴离子: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• 灰分: <0.1%
• 线性分子式: HO2CCH2CH(OH)CO2H

详细说明

MP Biomedicals - 02194700

Cell Culture Reagent
Crystalline
Free Acid
Purity: 99%

MP Biomedicals - 05214207

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102237

Crystalline
Free Acid
Purity: 99%

Sigma Aldrich - M7397

Biochem/physiol Actions
A TCA (Krebs cycle) intermediate and partner in the malic acid aspartate shuttle.

Sigma Aldrich - 112577

包装
25, 100 g in poly bottle
Application
用作氨基酸衍生物的选择性 α-氨基保护试剂。1 多功能合成子，用于制备包括 κ-阿片受体激动剂、2 1α,25-二羟基维生素 D3 类似物3和磷内酯霉素 B 在内的手性化合物。4

Sigma Aldrich - 02288

法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 02290

Other Notes
制备 (S) 2-乙酰氧基琥珀酰氯?1；制备 1-苹果酸单甲酯2,3；制备羟基琥珀酰亚胺衍生物4；通过二噁茂烷酮进行立体选择性 α-烷基化反应?5

Toronto Research Chemicals - M159505

The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece

参考文献

• Rindi, G., et al.: Biochem. J., 80, 214 (1961)
• Wolfgang, M., et al.: J. Biol. Chem., 281, 37265 (1961)
• Navarro, D., et al.: Metab. Brain Dis., 23, 115 (1961)
• Resolving agent for chiral amines; see, for example: Org. Synth. Coll., 2, 506 (1943).