HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid
C00496 · Ubiquitin-13C,15N human · ubiquitin cross-reactive protein · Ubiquitin-13C,15N human >=98 atom %, >=90% (CP), recombinant, expressed in E. coli
Identifiers & Physical Properties
| CAS No. | 60267-61-0 |
|---|---|
| Molecular formula | C6H8O7 |
| Average molar mass | 192.12 g/mol |
| Monoisotopic mass | 192.02700259 g/mol |
| SMILES | O=C(O)CC(O)(CC(=O)O)C(=O)O |
| InChIKey | KRKNYBCHXYNGOX-UHFFFAOYSA-N |
| PubChem CID | 311 |
| ChEMBL | CHEMBL1261 |
| ChEBI | CHEBI:30769 |
| EC No. | 201-069-1 |
| DTXSID | DTXSID3020332 |
Chemical & Physical Properties
| XLogP | -1.7 |
|---|---|
| Topological polar surface area | 132 |
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 5 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 227 |
| LogP (partition coefficient) | -1.64log Kow = -1.64-1.7 |
| LogS | 0.51 |
| Odor | Odorless |
| Taste | Strongly acidic tastePleasant, sweet, tart taste |
| Density | 1.54 at 68 °F (USCG, 1999) - Denser than waterwill sink1.665 g/cu cm at 20 °CBULK DENSITY: 56.2 LB/CU FTHEAT OF SOLN: -3.9 KCAL/MOLEBUFFERING INDEX: 2.46STD FREE ENERGY OF ANION FORMATION: -278.8 KCAL FOR AQ SOLN @ 25 °CDensity: 1.542 g/cu cm /Citric acid monohydrate/White, odorless crystals, granules or powdercool, saline taste. Stable in air, becomes anhydrous at 150 °C. Density: 1.814. Soluble in 3 parts water, 0.6 parts boiling water. Insoluble in alcohol. The aqueous solution is slightly alkaline to litmus. pH about 8 /Sodium citrate dihydrate/ |
| Viscosity | 2.549 cP 30% aqueous solution at 20 °C |
| Color/Form | Crystalsmonoclinic holohedracrystallizes from hot concentrated aqueous solutionColorless, translucent crystals or powderRhombic crystals from water with 1 mol of water of crystallization |
| Solubility | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)592000Very soluble in waterfreely soluble in ethanolsoluble in etherIn water, 3.83X10+5 mg/L at 25 °CSolubility in water: 54.0% w/w at 10 °C59.2% at 20 °C64.3% at 30 °C68.6% at 40 °C70.9% at 50 °C73.5% at 60 °C76.2% at 70 °C78.8% at 80 °C81.4% at 90 °C84.0% at 100 °CVery soluble in ethanolsoluble in ether, ethyl acetateinsoluble in benzene, chloroformTris-HCl, pH 7.5: 1.0—1.10mg/mL, clear to slightly hazy, colorless |
| Corrosivity | WILL CORRODE COPPER, ZINC, ALUMINUM AND THEIR ALLOYS |
| Flash point | 100 °C |
| Boiling point | Decomposes (NTP, 1992) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes.Behavior in fire: melts and decomposes. The reaction is not hazardous.Decomposes at 175 °C |
| Storage conditions | -20°C |
| Physical state | saline suspension |
| Biological source | human |
| UNSPSC Code | 41106500 |
| NACRES | NA.56 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | WGK 3 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264+P265, P271, P280, P304+P340, P305+P351+P338, P319, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 8.2% (359 of 4373) of reports. |
|---|---|
| Regulatory information | Chemical: 1,2,3-Propanetricarboxylic acid, 2-hydroxy-Regulation (EC) No 1331/20081,2,3-Propanetricarboxylic acid, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2,3-Propanetricarboxylic acid, 2-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 08-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15451Citric acid: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Citric acid: Human health tier II assessmentIMAP assessments - 1,2,3-Propanetricarboxylic acid, 2-hydroxy-: Environment tier I assessment |
| Fire hazards | Behavior in Fire: Melts and decomposes. The reaction is not hazardous. (USCG, 1999)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Fire potential | Combustible liquid |
| Health hazards | Inhalation of dust irritates nose and throat. Contact with eyes causes irritation. (USCG, 1999) |
| Hazards summary | An irritant to the throat and eyes[CAMEO] Concentrated solutions can cause severe eye damage and blindnessAnimals fed 1.2% citric acid for 90 weeks showed no adverse effects except erosion of tooth enamel. [CHEMINFO] |
| FDA requirements | Substance added directly to human food affirmed as generally recognized as safe (GRAS).Citric acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.Citric acid used as a sequestrant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: citric acid is included in weight control drug products. |
| Reactive group | Acids, CarboxylicAlcohols and Polyols |
| Special Reports | Leung HW, Paustenbach DJOrganic Acids and Bases: Review of Toxicological StudiesAm J Ind Med 18 (6): 717-35 (1990).USEPA/Office of Prevention, Pesticides and Toxic SubstanceReregistration Eligibility Decision Document - Citric Acid (June 1992). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of August 30, 2013: http://www.epa.gov/pesticides/reregistration/status.htm] |
| EPA Safer Chemical | Chemical: Citric acid, anhydrousGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
| FIFRA requirements | Unless specifically excluded, residues resulting from the use of the following substance as either an inert or an active ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemicals, is exempted from the requirement of a tolerance under FFDCA section 408, if such use is in accordance with good agricultural or manufacturing practices. Citric acid is included on this list.Section 4(g)(2)(A) of FIFRA requires the Agency to determine, after consideration of relevant data concerning an active ingredient whether products containing the active ingredient are eligible for reregistration. For products containing citric acid as an active ingredient the Agency has waived all generic data requirements except for those basic product identity and chemistry. These data were submitted and reviewed. In addition to these data, the Agency has considered the factors ... regarding citric acid's natural occurrence, common use as a food item, and the lack of reported adverse effects information. The Agency has completed its consideration of these data and other factors and has determined this information is sufficient to support reregistration of products containing citric acid as an active ingredient.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Citric acid is found on List D. Case No: 021801Pesticide type: fungicide/ antimicobialCase Status: RED Approved 08/92 - OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) Document.Active ingredient (AI): Citric acidAI Status: RED Completed - OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI. |
| Reactivity Profile | CITRIC ACID reacts with oxidizing agents, bases, reducing agents and metal nitrates (NTP, 1992). Reactions with metal nitrates are potentially explosive. Heating to the point of decomposition causes emission of acrid smoke and fumes [Lewis]. |
| Fire fighting | Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)Use water spray, powder, foam, carbon dioxide. |
| First aid measures | Fresh air, rest. Refer for medical attention.Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Safe storage | Separated from strong oxidants, strong bases, metal nitrates and metals. Dry. |
| Exposure control and personal protection | 2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| Fire fighting procedures | Extinguish with/ water, foam, dry chem, carbon dioxide. |
| Storage conditions | Crystalline citric acid, anhydrous, can be stored in dry form without difficulty, although conditions of high humidity and elevated temperatures should be avoided to prevent caking. Storage should be in tight containers to prevent exposure to moist air. Several granulations are commercially available with the larger particle sizes having less tendency toward caking.Temperature: ambientVenting: open.Containers: 230 lb Barrels, bags, kegs, boxes, cartons, fiber drums, bottles.Separated from strong oxidants, strong bases, metal nitrates and metals. Dry. |
| Cleanup methods | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. (NTP, 1992) |
| Disposal methods | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Inject at base of incinerator equipped with afterburner. Flammable solvent may be added. |
| Spillage disposal | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. |
| Preventive Measures | Do not eat, drink, or smoke during work.Closed system, ventilation, explosion-proof electrical equipment and lighting. Prevent deposition of dust.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Body burden | Citric acid was found to be excreted by humans through urine at a rate of 3-17 mg/kg body weight/day and through sweat at 0.2 mg/100 mL(1). |
| Interactions | ... Citric acid aerosol inhalation caused decreases in dynamic respiratory compliance and forced expiratory volume in 0.1 s (FEV0.1). This airway constriction was significantly attenuated by MK-886, mepyramine, cromolyn sodium, and compound 48/80, but not by either methysergide or indomethacin. Both LTC4 and histamine infusion significantly increased the magnitude of citric acid-induced airway constriction in compound 48/80-pretreated guinea pigs. Citric acid inhalation caused significant increase in histamine level in the bronchoalveolar lavage sample, which was significantly suppressed by compound 48/80.The relative efficacy of citric, malic, malonic, oxalic and succinic acids, and deferoxamine mesylate on the toxicity, distribution and excretion in mice exposed to aluminum were compared. Chelating agents were administered ip at a dose equal to one-fourth of their respective LD50. To determine the effect of the various chelators on the toxicity of aluminum, various doses of aluminum nitrate (938-3188 mg/kg) were administered ip, followed by one of the chelators. Survival was recorded at the end of 14 days. ... Malic acid and deferoxamine mesylate were the most effective in increasing the urinary excretion of aluminum. Citric acid was the most effective in increasing the fecal excretion of aluminum. Malonic, oxalic and succinic acids had no overall beneficial effects. Citric acid would appear to be the most effective agent of those tested in the prevention of acute aluminium intoxication.... When aluminum hydroxide and citric acid (133 mg Al/kg and 62 mg/kg, respectively) were simultaneously given orally to mice, fetal skeletal development defects resulted.The primary purpose of this study was to determine the relative usefulness of various measures to monitor body aluminum burden in weanling rats fed various amounts of aluminum (0.39 umol aluminum/g diet for 29 days, approximately 40 umol aluminum/g diet with or without citrate for 29 days and approximately 100 umol aluminum/g diet with citrate for 12 or 29 days) or injected ip with graded doses of aluminum (0.01, 4.6, 11.8, 23.5 or 94 umol aluminum). Twenty four hours prior to sacrifice, all rats were injected ip with either desferrioxamine (75 mg) or buffer. All seven indices of aluminum exposure monitored (eg: tibia, liver, kidney and serum aluminum concnchanges in serum aluminum concn in response to desferrioxamineurinary aluminum excretion with and without desferrioxamine treatment) were highly (p< 0.001) correlated to parenteral aluminum exposure. Ingestion of citrate had small but significant effects on aluminum retention. /Citrate/For more Interactions (Complete) data for CITRIC ACID (7 total), please visit the HSDB record page. |
| Ecotoxicity values | LC50Species: Carcinus maenas (Green or European shore crab)Conditions: renewalConcentration: 160 mg/L for 48 hr /formulated product/ |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that citric acid is expected to have very high mobility in soil(SRC). The pKa of citric acid is 2.79(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Citric acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.66X10-8 mm Hg at 25 °C(5). Citric acid reached 53% of its theoretical BOD in 5 days using a sludge inoculum(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that citric acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 2.79(3) indicates citric acid will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -1.64(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Theoretical biodegradation values of 66.4% and 67.3% after 5 days using freshwater and seawater inoculums, respectively(6), indicate that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), citric acid, which has an estimated vapor pressure of 1.7X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase citric acid may be removed from the air by wet and dry deposition(SRC). Citric acid absorbs light at wavelengths up to 260 nm(3) and, therefore, is not expected to be susceptible to direct photolysis since sunlight consists of wavelengths above 290 nm(SRC). |
| Food survey values | Plants containing citric acid, concentrations reported(1).Table: Reported Concentrations [Table#2404]Plants containing citric acid, concentrations not reported(1).Table: Detected, Not Quantified [Table#2405]Citric acid was detected as a flavoring constituent of farine collected from St. Lucia in the Caribbean(1). Citric acid was detected in 6 edible mushroom species sampled in Portugal in 2003. Concentrations were reported as follows (mg/kg and in combination with ketoglutaric acid): Amanita caesarea 452.07Boletus edulis 432.89-785.45Gyroporus castaneus 1282.85Lactarius deliciosus 92.97-6112-72Suillus collintus 362.73-2903.02and Xerocomus chrysenteron 377.97(2).MID, TO INCR EFFECTIVENESS OF ANTIOXIDANTS IN LARD, SHORTENING, & UNSMOKED DRY SAUSAGE@ 0.01% ALONE OR WITH ANTIOXIDANTS IN LARD OR SHORTENING0.001% IN ... SAUSAGE WITH 0.003% BHA. |
| Adverse effects | Dermatotoxin - Skin burns. |
| Exposure routes | The substance can be absorbed into the body by inhalation and by ingestion. |
| Toxicity summary | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Ecotoxicity excerpts | /OTHER TERRESTRIAL SPECIES/ The entomopathogenic fungus, Beauveria bassiana, produced citric acids in liquid cultures containing grasshopper (Melanoplus sanguinipes) cuticle as the sole nutrient source. Citric acids solubilized cuticular proteins as well as commercial preparations of elastin and collagen. Melanoplus sanguinipes treated with Beauveria bassiana showed a LT50 of 7.33 days, while Melanoplus sanguinipes treated with citric acid showed a LT50 of 7.25 and 13.28 days, respectively. Melanoplus sanguinipes treated with citric acid followed by a Beauveria bassiana conidia treatment showed a LT50 of 3.88 days. Analysis of the bioassay data revealed that the relationship between citric acid together with Beauveria bassiana conidia in grasshopper mortality was markedly synergistic. It is suggested that acid metabolites produced by Beauveria bassiana may play a role in cuticle solubilization and subsequent hyphal penetration. |
| Signs and Symptoms | Cough. Shortness of breath. Sore throat.Redness.Redness. Pain.Abdominal pain. Sore throat. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of citric acid can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that citric acid is expected to have very high mobility in soil. The pKa of citric acid is 2.79(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). A 2 uM solution of citric acid in Gulfstream seawater showed equilibrium absorption values of 79% and 94% onto 0.01 and 0.25 g of hydroxyapatite, respectively(5). |
| Natural Pollution Sources | Citric acid is widely distributed in plants and in animal tissues and fluids(1). It is extremely widespread in plants and has been identified in flowers of Hibiscus subdariffa(3).In nature, the citric acid cycle (Krebs cycle, TCA cycle, tricarboxylic acid cycle) is a series of enzymatic reactions occurring in living cells of aerobic organisms, the net result of which is the conversion of pyruvic acid, formed by anaerobic metabolism of carbohydrates, into carbon dioxide and water. The metabolic intermediates are degraded by a combination of decarboxylation and dehydrogenation. It is the major terminal pathway of oxidation in animal, bacterial, and plant cells. Recent research indicates that the TCA cycle may have predated life on earth and may have provided the pathway for formation of amino acids(1). |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | WGK 3 |
| Storage class | 11 - Combustible Solids |
Applications & Uses
Uses
Ubiquitin, N-terminal FLAG-tagged can replace the ubiquitin in formation of poly-ubiquitin—protein conjugates. The FLAG tag enables separation and enrichment of the protein conjugates on anti-FLAG affinity columns and detection of conjugates in western blot by anti-FLAG antibodies.
General Description
Ubiquitin, a globular protein is made of 76 amino acids and has lysine residues on its surface. It has a molecular weight of 8565 Da.