Physicochemical Properties
| Molecular Formula | C6H10O8 |
| Molecular Weight | 210.1388 |
| Exact Mass | 210.037 |
| CAS # | 5949-29-1 |
| Related CAS # | Citric acid;77-92-9;Ferric citrate;3522-50-7 |
| PubChem CID | 22230 |
| Appearance | White to off-white solid powder |
| Density | 1.54 |
| Boiling Point | 56 °C760 mm Hg(lit.) |
| Melting Point | 135-152 ºC |
| Flash Point | 173.9 ºC |
| Vapour Pressure | 184 mm Hg ( 20 °C) |
| Index of Refraction | n20/D 1.359(lit.) |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 14 |
| Complexity | 227 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | YASYEJJMZJALEJ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C6H8O7.H2O/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);1H2 |
| Chemical Name | 2-hydroxypropane-1,2,3-tricarboxylic acid;hydrate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In a dose-dependent manner, citric acid monohydrate (0–12.5 mM; 24 h) has antiproliferative action [3]. In G2/M and S phases, citric acid monohydrate (12.5 mM; 72 h) dose-dependently promotes apoptosis and cell cycle arrest [3]. The expression of FAS, BAX, BID, AIF, EndoG, cytochrome c, PARP, GADD153, GRP78, and caspase-3, -8, and -9 was upregulated and the expression of BCL-2 and BCL-Xl was downregulated when exposed to 12.5 mM of citric acid monohydrate for 48 hours[3]. |
| ln Vivo | In mouse livers, intraperitoneal injections of citric acid monohydrate (120, 240, and 480 mg/kg) can dramatically lower GSH-Px activity and raise MDA (malondialdehyde) levels [1]. In mouse hepatocytes, citric acid monohydrate (120, 240, and 480 mg/kg; i.p.) causes apoptosis by dose-dependently raising caspase-3 activity [1]. Mice exposed to intraperitoneal injections of citric acid monohydrate (120, 240, and 480 mg/kg; once weekly for three weeks) develop nephrotoxicity [2]. |
| Cell Assay |
Cell Viability Assay[3] Cell Types: HaCaT Cell Tested Concentrations: 0, 2.5, 5, 7.5, 10, 12.5 mM Incubation Duration: 24 hrs (hours) Experimental Results: Inhibition of cell viability in a dose-dependent manner. Cell cycle analysis[3] Cell Types: HaCaT Cell Tested Concentrations: 12.5 mM Incubation Duration: 0, 12, 24, 48, 72 hrs (hours) Experimental Results: Induced apoptosis and cell cycle arrest in G2/M phase and S in a dose-dependent manner Expect. Western Blot Analysis[3] Cell Types: HaCaT Cell Tested Concentrations: 12.5 mM Incubation Duration: 12, 24, 48 hrs (hours) Experimental Results: Increased expression of FAS, BAX, BID, AIF, EndoG, cytochrome c, PARP, GADD153, GRP78 and caspase -3, -8, -9, and BCL-2 and BCL-X1 were diminished. |
| Animal Protocol |
Animal/Disease Models: 20 g male Kunming mice [2] Doses: 120, 240, 480 mg/kg Route of Administration: intraperitoneal (ip) injection; once a week for 3 weeks. Experimental Results: The activities of T-SOD and GSH-Px in the treatment group diminished with the increase of citric acid dose, the activity of NOS demonstrated an increasing trend, and the contents of H2O2 and MDA gradually diminished. |
| References |
[1]. Study on injury effect of food additive citric acid on liver tissue in mice. Cytotechnology. 2014 Mar;66(2):275-82. [2]. Chen X, Lv Q, Liu Y, Deng W. Effects of the food additive, citric acid, on kidney cells of mice. Biotech Histochem. 2015 Jan;90(1):38-44. [3]. Citric acid induces cell-cycle arrest and apoptosis of human immortalized keratinocyte cell line (HaCaT) via caspase- and mitochondrial-dependent signaling pathways. Anticancer Res. 2013 Oct;33(10):4411-20. |
| Additional Infomation |
Citric acid monohydrate is an organic molecular entity. Citric Acid Monohydrate is a tricarboxylic acid found in citrus fruits. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It maintains stability of active ingredients and is used as a preservative. It is also used as an acidulant to control pH and acts as an anticoagulant by chelating calcium in blood. 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. See also: Citric Acid (broader); Citric Acid Monohydrate; Potassium Citrate (component of); Citric Acid monohydrate; Sodium Bicarbonate (component of) ... View More ... |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~475.87 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7587 mL | 23.7937 mL | 47.5873 mL | |
| 5 mM | 0.9517 mL | 4.7587 mL | 9.5175 mL | |
| 10 mM | 0.4759 mL | 2.3794 mL | 4.7587 mL |