2-hydroxypropane-1,2,3-tricarboxylic acid

• ChemBase ID: 3882
• Molecular Formular: C6H8O7
• Molecular Mass: 192.12352
• Monoisotopic Mass: 192.0270026
• SMILES: C(=O)(O)C(CC(=O)O)(CC(=O)O)O
• Canonical SMILES: OC(=O)C(CC(=O)O)(CC(=O)O)O
• InChI: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: KRKNYBCHXYNGOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropane-1,2,3-tricarboxylic acid
• IUPAC Traditional name: citro
• Synonyms: beta-Hydroxytricarballylic Acid; Citreoviridin; CITRIC ACID ANHYDROUS U.S.P.; 2-hydroxypropane-1,2,3-tricarboxylic acid; 3-carboxy-3-hydroxypentanedioic acid; 2-hydroxy-1,2,3-propanetricarboxylic acid; CITRIC ACID ANHYDROUS ELECTROPHORESIS GRADE; Citric acid solution; Citrate standard for IC; Citric acid, anhydrous, ACS; Citric Acid; CITRIC ACID ANHYDROUS; Citric acid; Acidum citricum anhydricum; 柠檬酸 溶液; IC 柠檬酸根标准品; 柠檬酸, 无水, ACS; 柠檬酸; 无水柠檬酸

Database IDs

• CAS Number: 77-92-9
• EC Number: 201-069-1; 231-791-2
• MDL Number: MFCD00011669
• Beilstein Number: 782061
• Merck Index: 142326
• PubChem SID: 24893049; 24856611; 24892700; 160967318; 24854425; 24864122; 24870585; 24892327; 24855122; 24856613; 24856608; 24856191; 24900992
• PubChem CID: 311
• CHEBI ID: 30769
• ATC CODE: A09AB04
• CHEMBL: 1261
• Chemspider ID: 305
• DrugBank ID: DB04272
• FEMA ID: 2306
• KEGG ID: D00037
• Unique Ingredient Identifier: XF417D3PSL
• Wikipedia Title: Citric_acid
• Council of Europe Number: 20c
• E Number: E330

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0479515
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -4.949584
• LogD (pH = 7.4): -9.468992
• Log P: -1.3226875
• Molar Refractivity: 35.6239 cm^3
• Polarizability: 14.4795475 Å^3
• Polar Surface Area: 132.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.33
• LOG S: -0.26
• Solubility (Water): 1.06e+02 g/l

PROPERTIES

Physical Property

• Solubility: 73 g/100 ml (20 °C) in water; H2O: soluble1 M at 20 °C, clear, colorless
• Apperance: Crystalline; crystalline white solid; grit
• Melting Point: 153°C; 153-154°C; 153-159 °C(lit.); ca. 153 °C with decomposition
• Boiling Point: 175°C (decomposes)
• Flash Point: ca. 345 °C (closed cup)
• Auto Ignition Point: 1010 °C (1850 °F)
• Density: 1.665; 1.665 g/cm^3 at 18 °C; 1.665 g/cm^3(1.5g/cm^3 for monohydrate)
• Vapor Pressure: Practically zero
• Absorption Wavelength: λ: 260 nm Amax: 0.20; λ: 280 nm Amax: 0.10
• pKa: (1) 3.13, (2) 4.76, (3) 6.4; (1) 3.13, (2) 4.76, (3) 6.40; pK_a1 = 3.09; pK_a2 = 4.75; pK_a3 = 5.41; pK_a3 = 6.39, 6.40
• pH: 1.0-2.0 (25 °C, 1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• RTECS: GE7350000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; nwg
• Risk Statements: 36; 37/38-41; 41; R:36/37/38
• Safety Statements: 26; 26-37/39; 26-37/39-60; 26-39; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• Main Hazard: skin and eye irritant
• NFPA704:
  

  1

  2

  0
• Explode Limits: 8 %, 65 °F
• GHS Hazard statements: H315-H318; H318-H315-H335-H303; H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• Regulation Compliance: FCC; FDA 21 CFR (131.111); FDA 21 CFR (131.112); FDA 21 CFR (133.123); FDA 21 CFR (133.124); FDA 21 CFR (133.129); FDA 21 CFR (133.169); FDA 21 CFR (133.173); FDA 21 CFR (133.178); FDA 21 CFR (133.179); FDA 21 CFR (145.134); FDA 21 CFR (145.145); FDA 21 CFR (146.187); FDA 21 CFR (150.141); FDA 21 CFR (150.161); FDA 21 CFR (155.130); FDA 21 CFR (161.190); FDA 21 CFR (163.11); FDA 21 CFR (163.110); FDA 21 CFR (163.112); FDA 21 CFR (169.115); FDA 21 CFR (169.140); FDA 21 CFR (169.150); FDA 21 CFR (172.755); FDA 21 CFR (172.861); FDA 21 CFR (173.160); FDA 21 CFR (173.165); FDA 21 CFR (173.280); FDA 21 CFR (178.1010); FDA 21 CFR (184.1033); FDA 21 CFR (73.85)

Pharmacology Properties

• Gene Information: human ... SRC(6714)
• Allergens: no known allergens

Product Information

• Purity: ≥99.5%; ≥99%; ≥99.5%; ≥99.5% (T); 95+%; 99%; 99.0-102.0% (ACS specification); 99.5+%; 99.5-100.5% (based on anhydrous substance); 99.5-100.5% anhydrous basis; 99+%
• Concentration: 1000 mg/L
• Grade: ACS reagent; analytical standard; anhydrous; certified reference material; ELECTROPHORESIS; FG; for luminescence; Kosher; NI; Ph Eur; puriss. p.a.; SAJ first grade; TraceCERT®; USP
• Packaging: ampule of 500 mg
• Suitability: cell culture tested; complies for appearance of solution; complies for reaction against H2SO4; in accordance for luminescence; meets USP testing specifications; plant cell culture tested
• Ignition Residue: ≤0.02%; ≤0.02% (as SO4); ≤0.05% (as SO4)
• Impurities: ≤0.0005% heavy metals (as Pb); ≤0.005% insolubles; ≤0.5% water (Karl Fischer); insoluble matter, passes filter test; organic volatile impurities, complies (GC); residual solvents, complies; Substances carbonizable by hot sulfuric acid, passes test
• Cation Traces: Al: ≤0.2 mg/kg; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; As: ≤1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤200 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤10 mg/kg; Cu: ≤5 mg/kg; Fe: ≤10 mg/kg; Fe: ≤3 mg/kg; Fe: ≤3 ppm; Fe: ≤5 mg/kg; Hg: ≤1 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤1 mg/kg; Pb: ≤2 mg/kg; Pb: ≤2 ppm; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤10 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤0.001%; chloride (Cl-): ≤5 mg/kg; chloride (Cl-): ≤50 mg/kg; oxalate (as oxalic acid): ≤100 mg/kg; oxalate (C2O42-): ≤500 mg/kg; oxalate (C2O42-): passes test (limit about 0.003%); phosphate (PO43-): ≤0.001%; phosphate (PO43-): ≤5 mg/kg; sulfate (SO42-): ≤0.002%; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤20 mg/kg; tartrate (C4H4O62-): ≤2000 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤0.5% loss on drying, 110 °C
• Quality Level: PREMIUM
• Quality: anhydrous; meets analytical specification of Ph. Eur., BP, USP, E330
• λ: 1 M in H2O
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• Pharmacopeia Traceability: traceable to PhEur A1202000; traceable to USP 1134368
• Linear Formula: HOC(COOH)(CH2COOH)2
• Empirical Formula (Hill Notation): C6H8O7
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02194641

Cell Culture Reagent
Anhydrous
Crystalline

MP Biomedicals - 04800680

Electrophoresis Grade
Anhydrous
Purity: >99.5%
Heavy metals: <10 ppm
Residue on Ignition: <0.05%
Water: <0.1%
A useful buffer component.

MP Biomedicals - 02101393

USP Grade
Anhydrous
Crystalline

MP Biomedicals - 04800681

Electrophoresis Grade
Anhydrous
Purity: =99.5%
Heavy metals: <10 ppm
Residue on Ignition: <0.05%
Water: <0.1%
A useful buffer component.

DrugBank - DB04272

• Drug Groups: experimental
• Description: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. [PubChem]

Sigma Aldrich - C4540

Application
除了用作铁螯合剂外，在细胞培养应用中柠檬酸盐还可支持胆固醇/甾醇、泛醌和类异戊二烯的生物合成。

Sigma Aldrich - W230618

Packaging
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in fiber drum

Sigma Aldrich - 94676

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 240621

Packaging
100 g in poly bottle

Sigma Aldrich - 38730

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

Sigma Aldrich - C2404

Application
除了用作铁螯合剂外，在细胞培养应用中柠檬酸盐还可支持胆固醇/甾醇、泛醌和类异戊二烯的生物合成。

Sigma Aldrich - C1857

Application
除了用作铁螯合剂外，在细胞培养应用中柠檬酸盐还可支持胆固醇/甾醇、泛醌和类异戊二烯的生物合成。

Sigma Aldrich - 251275

Packaging
100, 500 g in poly bottle
12 kg in fiber drum
2.5 kg in poly bottle
5 g in glass bottle

Sigma Aldrich - 27487

Other Notes
Buffer component for triple-column amino acid analysis1; Optimal buffer for dissociation of radioiodinated antibodies from viable murine tumor cells2
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 27487.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - C0759

包装
1 kg in poly bottle
5 kg in poly drum
500 g in poly bottle

Sigma Aldrich - C83155

Packaging
1 kg in poly bottle
4 kg in poly drum