Citric Acid

Base Information

• Chemical Name: Citric Acid
• CAS No.: 77-92-9
• Deprecated CAS: 12262-73-6,43136-35-2,245654-34-6,623158-96-3,856568-15-5,878903-72-1,890704-54-8,896506-46-0,906507-37-7,1192555-95-5,136108-93-5,2023788-69-2,1192555-95-5,136108-93-5,2023788-69-2,245654-34-6,43136-35-2,623158-96-3,856568-15-5,878903-72-1,890704-54-8,896506-46-0,906507-37-7
• Molecular Formula: C6H8O7
• Molecular Weight: 193.117
• Hs Code.: 2918.14 Oral rat LD50: 3000 mg/kg
• European Community (EC) Number: 201-069-1,920-306-6,921-454-4,680-681-4
• ICSC Number: 0855
• NSC Number: 759606,626579,30279
• UNII: XF417D3PSL
• DSSTox Substance ID: DTXSID3020332
• Nikkaji Number: J2.824J
• Wikipedia: Citric acid
• Wikidata: Q159683
• NCI Thesaurus Code: C80088
• RXCUI: 221946
• Pharos Ligand ID: S2C9CQ2VZQ1D
• Metabolomics Workbench ID: 37071
• ChEMBL ID: CHEMBL1261
• Mol file: 77-92-9.mol

Synonyms:Anhydrous Citric Acid;Citrate;Citric Acid;Citric Acid Monohydrate;Citric Acid, Anhydrous;Uralyt U

Chemical Property of Citric Acid

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 5.73E-05mmHg at 25°C
• Melting Point: 153-159 °C(lit.)
• Refractive Index: 1.493~1.509
• Boiling Point: 309.567 °C at 760 mmHg
• PKA: 3.14(at 20℃)
• Flash Point: 155.243 °C
• PSA: 132.13000
• Density: 1.762 g/cm³
• LogP: -1.24850
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: 750 g/L (20 ºC)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 192.02700259
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

99%,1, ^*data from raw suppliers

Citric Acid, Anhydrous, ACS ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C,T
• Statements: 41-36/37/38-36/38-37/38-34-36-35-61-60
• Safety Statements: 26-39-37/39-24/25-36/37/39-45-36-53

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Recent ClinicalTrials: Treatment for Calcium Phosphate Kidney Stone Disease
• Recent EU Clinical Trials: A Phase 2a, open-label, randomized, controlled, multi-center, proof of concept study, to assess the efficacy, safety and tolerability of VS-01 on top of standard of care, compared to standard of care alone, in adult patients with acute-on-chronic liver failure (ACLF) grades 1 and 2 and ascites
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the teeth. This may result in erosion.
• Biochemical Role: Citric acid is a 6-carbon tricarboxylic acid synthesized in the mitochondria through the condensation of oxaloacetate and acetyl-CoA by citrate synthase.; It serves as an intermediate in the mitochondrial tricarboxylic acid (TCA) cycle.; Citric acid is also involved in the glyoxylate cycle in plant cells.
• Biomedical Applications: Citrate-based biomaterials (CBBs) are biomaterials cross-linked with citric acid. These biomaterials exhibit advanced properties suitable for various biomedical applications, such as tunable mechanical properties, biocompatibility, and biofunctionality.
• Industrial Production and Market Demand: Citric acid is industrially produced through fermentation.; It is widely used in various industries including food and beverage, pharmaceuticals, detergents, and cosmetics. The food and beverage industry accounts for the largest portion of the global citric acid market.; There is a growing demand for citric acid due to its low cost, environmental friendliness, wide range of applications, and perceived natural status.
• Applications: In the food industry, citric acid is used as a food acidulant to prevent oxidative deterioration and improve taste and color in products.; In the pharmaceutical industry, sodium citrate, derived from citric acid, is used as an anticoagulant.; Citric acid is also used in cosmetics, chemical industry processes (e.g., electroplating, leather tanning), and as a replacement for phosphates in detergents.
• Emerging Applications: Citric acid properties are being explored for new applications such as in biodegradable packaging, disinfectants, fruit preservatives, and environmental remediation.

Technology Process of Citric Acid

There total 132 articles about Citric Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → carbon dioxide (124-38-9,18923-20-1) + 2-buten-4-olide (497-23-4) + benzaldehyde (100-52-7) + acetic acid (64-19-7,77671-22-8) + benzoic acid (65-85-0,8013-63-6) + citric acid (77-92-9,906507-37-7)

Guidance literature:

With SmMnO₃; at 350 ℃; Temperature; Reagent/catalyst; Catalytic behavior;

DOI:10.1021/acs.inorgchem.9b02518

Reference yield:

β-D-glucose (492-61-5) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4) + 2-methylisocitric acid + citric acid (77-92-9,906507-37-7)

Guidance literature:

With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S_. lipolytica;

Reference yield:

β-D-glucose (492-61-5) + L-methionine (63-68-3,26062-47-5,58576-49-1) → 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4) + 2-methylisocitric acid + citric acid (77-92-9,906507-37-7)

Guidance literature:

With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S_. lipolytica;

upstream raw materials:

ethanol

glyceric acid

mannitol

fructose

Downstream raw materials:

anhydroacetylcitric acid

4,7-dimethyl-coumarin

2-acetoxy-propane-1,2,3-tricarboxylic acid

triallyl citrate

Refernces

• 1、 Morgunov, Igor G.,Kamzolova, Svetlana V.,Karpukhina, Olga V.,Bokieva, Svetlana B.,Inozemtsev, Anatoly N.. "Biosynthesis of isocitric acid in repeated-batch culture and testing of its stress-protective activity". . . Retrieved 2019.
• 2、 Wehmer. "-". . p. 37. Retrieved 1913.
• 3、 Kirimura, Kohtaro,Watanabe, Taisei,Sunagawa, Tadahiro,Usami, Shoji. "Citric acid production from xylan and xylan hydrolysate by semi-solid culture of Aspergillus niger". . p. 226 - 228. Retrieved 1999.
• 4、 Kasai, Takanori,Shiroshita, Yoshinari,Uomoto, Katsuhito,Sakamura, Sadao. "ACIDIC Nα-ACYLARGININE DERIVATIVES IN ARGININE-ACCUMUTATING PLANT TISSUES". . p. 147 - 150. Retrieved 1983.
• 5、 Salmony. "-". . p. 902. Retrieved 1927.
• 6、 Wang, Feng,Huang, Po-Jung Jimmy,Liu, Juewen. "Citrate inhibition of cisplatin reaction with DNA studied using fluorescently labeled oligonucleotides: Implication for selectivity towards guanine". . p. 9482 - 9484. Retrieved 2013.
• 7、 Ellis, Holly R.,Kammerer, Bernd,Lagies, Simon,Matthews, Arne,Sch?nfelder, Julia,Schleicher, Erik,Stull, Frederick,Teufel, Robin. "Bacterial flavoprotein monooxygenase YxeK salvages toxic S-(2-succino)-adducts via oxygenolytic C–S bond cleavage". . . Retrieved 2021/10/06.