(2R,3R)-2,3-dihydroxybutanedioic acid

• ChemBase编号: 102772
• 分子式: C4H6O6
• 平均质量: 150.08684
• 单一同位素质量: 150.01643791
• SMILES: O=C(O)[C@H](O)[C@@H](O)C(=O)O
• Canonical SMILES: O[C@H]([C@H](C(=O)O)O)C(=O)O
• InChI: InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1
• InChIKey: FEWJPZIEWOKRBE-JCYAYHJZSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC传统名: L(+)-tartaric acid
• 别名: L-(+)-酒石酸, ACS; 酒石酸根 溶液; 酒石酸根 IC 标准品; (2R,3R)-(+)-酒石酸; 左旋酒石酸; L-(+)-酒石酸; L-2,3-Dihydroxybutanedioic acid; 2,3-Dihydrosuccinic acid; L-Threaric acid; L-(+)-TARTARIC ACID; 2,3-Dihydroxybutanedioic acid; L-(+)-Tartaric acid, ACS; L-(+)-TARTARIC ACID, ACS; Acidum tartaricum; Tartrate solution; Tartrate standard for IC; (2R,3R)-(+)-Tartaric acid; L-(+)-Tartaric acid; (2R,3R)-2,3-Dihydroxysuccinic acid

登记号

• CAS号: 87-69-4
• EC号: 231-791-2; 201-766-0
• MDL号: MFCD00064207
• Beilstein号: 1725147
• 默克索引号: 149070
• PubChem SID: 162088195; 24860511; 24873364; 24855129; 24901442; 24899993; 24899931; 24856623; 24856625; 24890127
• PubChem CID: 444305
• FEMA编号: 3044
• 欧洲委员会编号: 18

理论计算性质

• Acid pKa: 2.719041
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -5.323427
• LogD (pH = 7.4): -7.890869
• Log P: -1.8287998
• 摩尔折射率: 26.2134 cm^3
• 极化性: 10.871467 Å^3
• 极化表面积: 115.06 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: soluble1 M at 20 °C, clear, colorless; Soluble in water, methanol, ethanol, glycerol
• 外观: Granular; grit; powder
• 熔点: 166-170 °C; 168-170 °C; 168-170°C; 170-172 °C(lit.); 170-172°C
• 闪点: 150 °C; 302 °F
• 自燃点: 797 °F
• 密度: 1.760
• 蒸汽密度: 5.18 (vs air)
• 比旋光度: [α]20/D +12.0 to +12.8°, c = 20% in H2O; [α]20/D +12.4°, c = 20 in H2O; [α]20/D +12.5°, c = 20 in H2O; [α]20/D +12°, c = 20 in H2O; [α]20/D +13.5±0.5°, c = 10% in H2O; +12.4 (c=20 in water)
• 紫外吸收波长: λ: 260 nm Amax: 0.3; λ: 280 nm Amax: 0.20
• pH值: 1.0-2.0 (25 °C, 1 M in H2O)

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: WW7875000
• 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; R:36/37/38
• 安全公开号: 26; 26-37; S:20-25-26-37/39
• 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; Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (163.110); FDA 21 CFR (163.111); FDA 21 CFR (163.112); FDA 21 CFR (184.1099)

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥99%; ≥98%; ≥99.5%; ≥99.5% (T); ≥99.7%; 95+%; 99%; 99.5-101.0% (calc. to the dried substance); 99.7-100.5% (calc. to the dried substance)
• 浓度: 1.000 g/L; in H2O
• 级别: ACS; ACS reagent; analytical standard; FG; Halal; JIS special grade; NI; Ph Eur; puriss.; puriss. p.a.; REAGENT; SAJ first grade
• 光学纯度: ee: 99% (GLC)
• 适用性: complies for appearance of solution
• 燃烧残渣: ≤0.01% (as SO4); ≤0.02%; ≤0.02% (as SO4); ≤0.05% (as SO4); ≤0.1%; ≤0.1% (as SO4)
• 杂质: ≤0.0005% heavy metals (as Pb); ≤0.001% heavy metals (as Pb); ≤0.002% Phosphorus (P); ≤0.002% S compounds; ≤0.005% insolubles; ≤0.02% oxalic acid; ≤0.1% Insoluble matter; insoluble matter, passes filter test; organic volatile impurities, complies (GC); residual solvents, complies
• 痕量阳离子: Al: ≤0.002%; Al: ≤10 mg/kg; As: ≤0.1 mg/kg; As: ≤2 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.005%; Ca: ≤10 mg/kg; Ca: ≤20 mg/kg; Ca: ≤200 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤10 mg/kg; Cu: ≤0.0005%; Cu: ≤10 mg/kg; Cu: ≤5 mg/kg; Fe: ≤0.005%; Fe: ≤5 mg/kg; Fe: ≤5 ppm; heavy metals (as Pb): ≤5 ppm; Hg: ≤1 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Li: ≤50 mg/kg; Mg: ≤0.001%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤0.005%; Na: ≤50 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤2 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤10 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤0.001%; chloride (Cl-): ≤0.05%; chloride (Cl-): ≤100 mg/kg; chloride (Cl-): ≤5 mg/kg; oxalate (as oxalic acid): ≤100 mg/kg; oxalate (C2O42-): in accordance; oxalate (C2O42-): passes test; phosphate (PO43-): ≤0.001%; phosphate (PO43-): ≤10 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤150 mg/kg; sulfate (SO42-): ≤50 mg/kg
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤0.1% loss on drying, 105 °C; ≤0.1% loss on drying, 110 °C; ≤0.2% loss on drying, 105 °C; ≤0.2% loss on drying, 110 °C
• 品质说明: meets analytical specification of Ph. Eur., BP, NF, FCC, E334
• λ: 1 M in H2O
• 药典: testing & handling conforms to Pharmacopeia
• 产品线: BioUltra; BioXtra
• 线性分子式: HO2CCH(OH)CH(OH)CO2H
• Empirical Formula (Hill Notation): C4H6O6

详细说明

MP Biomedicals - 02103001

Free Acid
Crystalline
Purity: 99+%

MP Biomedicals - 02152586

ACS Reagent Grade

Sigma Aldrich - W304409

包装
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - 50824

Preparation Note
使用酒石酸和 H2O 制备
General description
经过 0.45μm 膜过滤器过滤

Sigma Aldrich - T109

包装
12 kg in fiber drum
500 g in poly bottle
3 kg in poly bottle

Sigma Aldrich - T1807

包装
1 kg in poly bottle
100, 500 g in poly bottle

Sigma Aldrich - 251380

包装
100, 500 g in poly bottle
2.5 kg in poly bottle
5 g in glass bottle
Application
天然产物的手性结构单元。1也可与 TiCl2(O-i-Pr)2 形成 Diels-Alder 反应催化剂。2

参考文献

• Resolving agent for chiral bases. For improved resolution technique using two immiscible solvents and half equivalent of resolving agent, claimed to give higher optical purities and faster resolutions than conventional methods, see: Tetrahedron, 41, 2465 (1985).
• In combination with NaBH ₄, induces asymmetric reduction of functionalized ketones with ee figures approaching those achieved with more expensive reagents: J. Chem. Soc. Perkin 1, 1826 (1990).
• Preferred acid catalyst, in combination with MgSO ₄, for acetalization of unsaturated aldehydes with ethylene glycol, giving less double bond isomerization than stronger acids including tosic and succinic: J. Org. Chem., 60, 2931 (1995).