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

• ChemBase ID: 102772
• Molecular Formular: C4H6O6
• Molecular Mass: 150.08684
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: L(+)-tartaric acid
• Synonyms: 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; 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

Database IDs

• CAS Number: 87-69-4
• EC Number: 231-791-2; 201-766-0
• MDL Number: MFCD00064207
• Beilstein Number: 1725147
• Merck Index: 149070
• PubChem SID: 24901442; 24856623; 24899993; 24899931; 162088195; 24860511; 24856625; 24873364; 24855129; 24890127
• PubChem CID: 444305
• FEMA ID: 3044
• Council of Europe Number: 18

CALCULATED PROPERTIES

• Acid pKa: 2.719041
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.323427
• LogD (pH = 7.4): -7.890869
• Log P: -1.8287998
• Molar Refractivity: 26.2134 cm^3
• Polarizability: 10.871467 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 M at 20 °C, clear, colorless; Soluble in water, methanol, ethanol, glycerol
• Apperance: Granular; grit; powder
• Melting Point: 166-170 °C; 168-170 °C; 168-170°C; 170-172 °C(lit.); 170-172°C
• Flash Point: 150 °C; 302 °F
• Auto Ignition Point: 797 °F
• Density: 1.760
• Vapor Density: 5.18 (vs air)
• Optical Rotation: [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)
• Absorption Wavelength: λ: 260 nm Amax: 0.3; λ: 280 nm Amax: 0.20
• pH: 1.0-2.0 (25 °C, 1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: WW7875000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: 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)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥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)
• Concentration: 1.000 g/L; in H2O
• Grade: ACS; ACS reagent; analytical standard; FG; Halal; JIS special grade; NI; Ph Eur; puriss.; puriss. p.a.; REAGENT; SAJ first grade
• Optical Purity: ee: 99% (GLC)
• Suitability: complies for appearance of solution
• Ignition Residue: ≤0.01% (as SO4); ≤0.02%; ≤0.02% (as SO4); ≤0.05% (as SO4); ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤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
• Cation Traces: 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
• Antion Traces: 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
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤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
• Quality: meets analytical specification of Ph. Eur., BP, NF, FCC, E334
• λ: 1 M in H2O
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra; BioXtra
• Linear Formula: HO2CCH(OH)CH(OH)CO2H
• Empirical Formula (Hill Notation): C4H6O6

DETAILS

MP Biomedicals - 02103001

Free Acid
Crystalline
Purity: 99+%

MP Biomedicals - 02152586

ACS Reagent Grade

Sigma Aldrich - W304409

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

Sigma Aldrich - 50824

Preparation Note
prepared with tartaric acid and H2O
General description
filtered through a 0.45 μm membrane filter

Sigma Aldrich - T109

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

Sigma Aldrich - T1807

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

Sigma Aldrich - 251380

Packaging
100, 500 g in poly bottle
2.5 kg in poly bottle
5 g in glass bottle
Application
Chiral building block for natural products.1 Also forms a Diels-Alder catalyst with TiCl2(O-i-Pr)2.2

REFERENCES

• 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).