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Citric acid(CAS No. 77-92-9)

Citric acid C6H8O7 (cas 77-92-9) Molecular Structure

77-92-9 Structure

Identification and Related Records

【Name】
Citric acid
【CAS Registry number】
77-92-9
【Synonyms】
2-Hydroxy-1,2,3-propanetricarboxylic acid
Citric acid, anhydrous, USP Grade 1,2,3-Propanetricarboxylic acid, 2 hydroxy-citric acid, anhydrous, USP Grade
Citric acid anhydrous
Citric acid anhydride
【EINECS(EC#)】
201-069-1
【Molecular Formula】
C6H8O7 (Products with the same molecular formula)
【Molecular Weight】
192.12
【Inchi】
InChI=1/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
【Canonical SMILES】
C(C(=O)O)C(CC(=O)O)(C(=O)O)O
【MOL File】
77-92-9.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.542g/cm3
【Melting Point】
153-154.5℃
【Boiling Point】
309.6 °C at 760 mmHg
【Refractive Index】
1.493~1.509
【Flash Point】
100℃
【Water】
750 g/L (20℃)
【Solubilities】
1 M at 20 °C in water, clear, colorless
【Color/Form】
Crystals; monoclinic holohedra; crystallizes from hot concentrated aqueous solution
Colorless, translucent crystals or powder
Rhombic crystals from water with 1 mol of water of crystallization
【Stability】
Stable. Incompatible with bases, strong oxidizing agents, reducing agents, metal nitrates.
【Storage temp】
Store at RT.
【Spectral properties】
SADTLER REFERENCE NUMBER: 765 (IR, PRISM)
IR: 5104 (Coblentz Society Spectral Collection)
1H NMR: 7552 (Sadtler Research Laboratories Spectral Collection)
MASS: 8394 (NIST/EPA/MSDC Mass Spectral Database 1990 version)
【Computed Properties】
Molecular Weight:192.12352 [g/mol]
Molecular Formula:C6H8O7
XLogP3:-1.7
H-Bond Donor:4
H-Bond Acceptor:7
Rotatable Bond Count:5
Exact Mass:192.027003
MonoIsotopic Mass:192.027003
Topological Polar Surface Area:132
Heavy Atom Count:13
Formal Charge:0
Complexity:227
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:7
Feature 3D Donor Count:1
Feature 3D Anion Count:3
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:48

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Safety】

Safety Information about?Citric Acid Anhydrous (CAS NO: 77-92-9):
Hazard Codes: Xi, C
Risk Statements: 41-36/37/38-34
41:?Risk of serious damage to eyes?
36/37/38:?Irritating to eyes, respiratory system and skin?
34:?Causes burns
Safety Statements: 26-24/25-36/37/39-45
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
24/25: Avoid contact with skin and eyes?
36/37/39: Wear suitable protective clothing, gloves and eye/face protection?
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR:?UN 1789 8/PG 3
WGK Germany : 1
F: 9: Keep under nitrogen.

【Sensitive】
Hygroscopic
【Skin, Eye, and Respiratory Irritations】
Inhalation of dust irritates nose and throat. Contact with eyes causes irritation.
【Cleanup Methods】
Addition of lime will neutralize and precipitate calcium citrate.
【Transport】
UN 1789 8/PG 3
【Fire Fighting Procedures】
/EXTINGUISH WITH/ WATER, FOAM, DRY CHEM, CARBON DIOXIDE.
【Fire Potential】
Combustible liquid
【Formulations/Preparations】
... Anticoagulant citrate dextrose solution, anticoagulant citrate phosphate dextrose solution, citric acid syrup, & effervescent salts.
Grades of purity: USP; reagent; monohydrate grade.
Grades: Both hydrous (hydrated) and anhydrous, Technical, Chemically Pure, United States Pharmacopeia, Food Chemical Codex.
Citric acid for pharmaceutical use: not 5% water; not >0.05% ash; not >0.001% heavy metals; not > 0.0003% As. Hydrous citric acid may contain up to 8.8% water
Liquid citric acid is commercially available in a variety of concentrations with 50% w/w being most common. Grades are available that vary in appearance, purity, and color.
【Exposure Standards and Regulations】
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.
【Reactivities and Incompatibilities】
Pharmaceutical incompatibilities: Potassium tartrate, alkali, and alkaline earth carbonates and bicarbonates, acetates, sulfides.
Potentially explosive reaction with metal nitrates.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.
【Protective Equipment and Clothing】
Inhalation of dust irritates nose and throat. Contact with eyes causes irritation.
【Specification】

Citric Acid Anhydrous (CAS NO: 77-92-9) is also called Citric acid anhydrous ; 2-Hydroxy-1,2,3-propanetricarboxylic acid ; 2-Hydroxytricarballylic acid .

【Octanol/Water Partition Coefficient】
log Kow = -1.64
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Inject at base of incinerator equipped with afterburner. Flammable solvent may be added.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

The microbial production of citric acid on a commercial scale was begun in 1923 utilizing certain strains of Aspergillus niger to produce citric acid on the surface of a sucrose and salt solution. This tray fermentation technique is still used today, although it is being replaced by a submerged process known as deep tank fermentation. In the deep tank submerged process, Aspergillus niger mold spores are grown under controlled aseptic conditions on a test-tube slant and transferred to a seed tank or inoculum which is added to a fermentor along with pasteurized syrup. The pH is adjusted and nutrients added. Sterile air is sparged into the fermentor while the sugar is converted to citric acid. The complete fermentation cycle can take as long as 15 days. ... Citric acid fermentation broth is generally separated from the biomass using filtration or centrifugation. The citric acid is usually purified using either a lime-sulfuric acid method or a liquid extraction process.
Mold fermentation of beet or sugar cane molasses, or dextrose (corn sugar)
Produced by mycological fermentation on an industrial scale using crude sugar solutions, such as molasses and strains of Aspergillus niger: ... Schweiger, US patent 2970084 (1961 to Miles Labs.)
...Extracted from citrus fruits (lemon juice contains 5 to 8%) and from pineapple waste.
By mold fermentation of carbohydrates, including deep fermentation, from lemon, lime, and pineapple juice, and from molasses.
U.S. Exports

(1972) 4.94X10+9 GRAMS
(1975) 4.2X10+9 GRAMS
(1985) 6.71X10+9 g
U.S. Imports

(1972) 1.46X10+8 GRAMS
(1975) 3.4X10+8 GRAMS
(1985) 1.96X10+10 g
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1990) Worldwide citric acid production: Western Europe 41.0%; North America 28.0%; Far East, Australia, and New Zealand 11.0%; South and Central America 9.0%; Remainder of the world 11.0%. /From table/
... 1990 worldwide production estimated at approximately 550,000 metric tons.
(1972) 7.6X10+10 GRAMS (EST)
(1976) 9.8X10+10 GRAMS (EST)
(1986) >100 million-500 million pounds
(1990) >100 million-500 million pounds
(1991) 3.86X10+8 lb
(1994) >100 million-500 million pounds
(1998) >100 million-500 million pounds
(2002) >100 million-500 million pounds
Consumption Patterns

73% IN FOODS & BEVERAGES AS AN ACIDULANT, PH REGULATOR, FLAVOR ENHANCER, PRESERVATIVE, & ANTIOXIDANT SYNERGIST; 16% IN PHARMACEUTICAL PREPARATIONS PRINCIPALLY IN EFFERVESCENT ANTACID POWDERS & TABLETS; 11% IN METAL CLEANING & FINISHING, & AS A CHEMICAL INTERMEDIATE FOR ESTERS & SALTS FOR DETERGENTS & PLASTICIZERS. )

Biomedical Effects and Toxicity

【Biological Activity】
Commonly used laboratory reagent
【Pharmacological Action】
- Agents that prevent clotting.
- Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
【Therapeutic Uses】
Mesh Heading: Anticoagulants, chelating Agents
IT HAS ... BEEN USED TO DISSOLVE URINARY BLADDER CALCULI, & AS MILD ASTRINGENT.
Citrate ... of ... value in alleviation of chronic metabolic acidosis ... from chronic renal insufficiency or syndrome of renal tubular acidosis ... usually prescribed in form of sodium citrate and citric acid soln, USP ...
Component of anticoagulant citrate solutions (citrate dextrose soln; citrate phosphate dextrose soln; citric acid syrup).
Potassium citrate, up to 10 g daily, has been used as a potassium supplement; the potassium and sodium salts have been used, in similar dosages, as mild diuretics in humans.
【Biomedical Effects and Toxicity】
/A portion/ of the circulating (mainly metabolic but also ingested) citric acid is excreted in urine, with 24-hour urine reference values between 1.5 and 3.68 mmol, corresponding to 0.29-0.71 g citric acid excreted per person per day.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.1(SRC), determined from a log Kow of -1.64(2) and a regression-derived equation(3), indicates that citric acid is expected to have very high mobility in soil(SRC). The pKa of citric acid is 2.79(4), indicating that this compound will primarily exist 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(5). Volatilization of citric acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-14 atm-cu m/mole(SRC) derived from its estimated vapor pressure, 1.66X10-8 mm Hg(6), and water solubility, 3.83X10+5 mg/L(7). Citric acid is not expected to volatilize from dry soil surfaces(SRC) based upon its estimated vapor pressure(6). Citric acid may be susceptible to biodegradation in terrestrial environments based on the observed degradation of 53-100% in sludge inoculum after time periods ranging from 1 to 42 days(8-10).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.1(SRC), determined from a log Kow of -1.64(2) and a regression-derived equation(3), indicates that citric acid is not expected to adsorb to suspended solids and sediment(SRC). The pKa of citric acid is 2.79(4), indicating that this compound will primarily exist 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(5). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-14 atm-cu m/mole(SRC) derived from its estimated vapor pressure, 1.66X10-8 mm Hg(6), and water solubility, 3.83X10+5 mg/L(7). According to a classification scheme(8), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Screening tests show that citric acid is readily biodegradable in aquatic environments reaching 53-100% degradation in sludge inoculum(10-12) and 66.4% and 67.3% of its theoretical BOD after 5 days using freshwater and seawater inoculums, respectively(13).
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 1.66X10-8 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase citric acid may be removed from the air by wet or dry deposition(SRC). Citric acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).

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