Citric acid

A naturally occurring tricarboxylic acid found in citrus fruits and produced in cellular metabolism as an intermediate of the tricarboxylic acid (Krebs) cycle. Citric acid participates in energy metabolism and exhibits metal-ion chelating properties. It is widely used as an acidulant, pH regulator, preservative adjunct, and pharmaceutical excipient, as well as in citrate-based formulations for urinary alkalinization

CAS Number: 77-92-9

Molecular Mass: 192.12 g/mol

Formula: C₆H₈O₇

Smiles: O=C(O)CC(O)(CC(=O)O)C(=O)O

Synonymes:

Citric acid, citric acid, 77-92-9, 2-hydroxypropane-1,2,3-tricarboxylic acid, Citric acid, anhydrous, Aciletten, Anhydrous citric acid, Citro, Citretten, Citric acid anhydrous, Chemfill, Hydrocerol A, 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 2-hydroxy-1,2,3-propanetricarboxylic acid, Kyselina citronova, 2-Hydroxytricarballylic acid, beta-Hydroxytricarballylic acid, 3-Carboxy-3-hydroxypentane-1,5-dioic acid, FEMA No. 2306, FEMA Number 2306, Citric acid,anhydrous, Citricum acidum, Citric acid monoglyceride, Acidum citricum, Citric acid bp, XF417D3PSL, NSC-30279, Citric acid,hydrous, NSC-626579, Citric acid, hydrous, DTXSID3020332, NSC30279, NSC-112226, E330, DTXCID50332, 2-hydroxy-1,2,3-propanetricarboxyic acid, INS NO.330, CHEBI:30769, INS-330, B1650, E-330, CLENPIQ COMPONENT ANHYDROUS CITRIC ACID, 2-hydroxy-1,2,3-propane-tricarboxylic acid, Bio-Active, Pleo Citro, Urologic G, ACD Solution Modified, RefChem:6630, Citric Buffered Normal Saline, BETA-HYDROXY-TRICARBOXYLIC ACID, 2-(carboxymethyl)-2-hydroxybutanedioate, hydron, 2-Hydroxy-1,2,3-propanetricarboxylic Acid, Anhydrous, 201-069-1, 680-681-4, 920-306-6, 921-454-4, hydron, 2-hydroxypropane-1,2,3-tricarboxylate, Caswell No. 221C, 2-Hydroxypropanetricarboxylic acid, C6H8O7, K-Lyte, Kyselina citronova [Czech], K-Lyte DS, CCRIS 3292, HSDB 911, EPA Pesticide Chemical Code 021801, Uro-trainer, AI3-06286, Suby G, NSC 30279, NSC 626579, BRN 0782061, MFCD00011669, 79586-22-4, CHEMBL1261, Kyselina 2-hydroxy-1,2,3-propantrikarbonova [Czech], Kyselina 2-hydroxy-1,2,3-propantrikarbonova, Ubiquitin, .beta.-Hydroxytricarballylic acid, citr, NSC626579, Citric acid, 99%, NCGC00090954-03, E 330, 1,2,3-Tricarboxy-2-hydroxypropane, , Citric acid [USAN:JAN], CAS-77-92-9, 141633-96-7, 1,3-Propanetricarboxylic acid, 2-hydroxy-, FLC, EINECS 201-069-1, UNII-XF417D3PSL, Citraclean, Citronensaeure, citric-acid, Citric Acid Anhydrous, 2-Hydroxypropane-1,2,3-tricarboxylic acid, Anhydrous citrate, 2fwp, 4aci, 4nrm, H3cit, Citric acid, anhydrous [USP:JAN], Citric acid (8CI), K-Lyte (Salt/Mix), 1i2s, 1o4l, 1rq2, 1y4a, 2bo4, 2c4v, 2fw6, 4to8, Citraclean (Salt/Mix), Citric Acid (Anhydrous), Spectrum3_001850, WLN: QV1XQVQ1VQ, beta-Hydroxytricarballylate, cid_311, K-Lyte/Cl (Salt/Mix), CITRIC ACID [MI], K-Lyte DS (Salt/Mix), SCHEMBL842, bmse000076, HOC(CH2COOH)2COOH, EC 201-069-1, CITRIC ACID [FHFI], CITRIC ACID [HSDB], NCIStruc1_000057, NCIStruc2_000099, NCIOpen2_004062, NCIOpen2_004502, Oprea1_502996, BSPBio_003240, Citric acid (anhydrous) CRS, 134367-01-4, 4-03-00-01272 (Beilstein Handbook Reference), Citric Acid, anhydrous, USP, MLS001066346, CITRIC ACID [WHO-DD], Citric acid, anhydrous (USP), CITRICUM ACIDUM [HPUS], Anhydrous citric acid (JP18), GTPL2478, orb1301333, orb3140422, Citric acid, analytical standard, BDBM14672, BETZ 6251, Citric acid, p.a., 99.5%, KBio3_002740, Citric Acid, anhydrous, granular, MSK4426, 4o61, Citric acid, Electrophoresis Grade, HMS1787N01, HMS2268B04, HMS5085B05, Pharmakon1600-01300013, ANHYDROUS CITRIC ACID [II], ANHYDROUS CITRIC ACID [JAN], HY-N1428, STR12052, 1,2,3-Tricarboxy-2-hydroxypropane, Tox21_113436, Tox21_202405, Tox21_300124, BBL002530, EBC-26171, NSC759606, s5761, SBB008922, STK286098, Citric Acid, anhydrous granular, ACS, CITRIC ACID,ANHYDROUS [VANDF], AKOS000119911, ANHYDROUS CITRIC ACID [MART.], Citric Acid, anhydrous, fine granular, Citric acid, LR, anhydrous, >=99%, ACIDUM CITRICUM [WHO-IP LATIN], CS-6965, DB04272, FC02313, T5S0636, 3-Carboxy-3-hydroxypentane-1,5-dioate, Citric acid, >=99.5%, FCC, FG, Citric acid, ACS reagent, >=99.5%, Citric Acid, anhydrous powder, A.C.S., 2-Hydroxy-1,3-propanetricarboxylic acid, CITRIC ACID, ANHYDROUS [WHO-IP], NCGC00090954-01, NCGC00090954-02, NCGC00090954-04, NCGC00090954-05, NCGC00090954-06, NCGC00254055-01, NCGC00259954-01, 2-hydroxypropane-1,2,3-tricarboxylicacid, BP-31028, DA-72240, NCI60_022579, SMR000471840, SBI-0206765.P001, Citric acid, SAJ first grade, >=99.5%, 2-Hydroxy-1,2,3-propane tricarboxylic acid, ANHYDROUS CITRIC ACID [USP MONOGRAPH], C1949, CITRIC ACID, ANHYDROUS [EP IMPURITY], Citric acid, Vetec(TM) reagent grade, 99%, NS00007335, ST50308093, 1,2,3-Propanetricarboxylio acid, 2-hydroxy-, CITRIC ACID, ANHYDROUS [USP IMPURITY], EN300-16683, C00158, D00037, G91031, SBI-0206765.0002, AE-562/40806920, Citric acid, BioUltra, anhydrous, >=99.5% (T), F044712, Q159683, 1,2,3-Propanetricarboxylic acid, 2-hydroxy- (9CI), BRD-K76792669-001-08-1, Citric acid, certified reference material, TraceCERT(R), Citric acid, meets USP testing specifications, anhydrous, F2191-0222, 8F5D336A-442D-434A-9FB0-E400FF74E343, Citrate standard for IC, 1000 mg/L, analytical standard, 1,2,3-PROPANETRICARBOXYLIC ACID,2-HYDROXY (CITRIC ACID), Citric acid, United States Pharmacopeia (USP) Reference Standard, CITRIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC], Citric acid, anhydrous, cell culture tested, plant cell culture tested, Citric acid, anhydrous, European Pharmacopoeia (EP) Reference Standard, Citric acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.5%, CITRIC ACID (CONSTITUENT OF GARCINIA CAMBOGIA AND GARCINIA INDICA) [DSC], Citric acid, Anhydrous, Pharmaceutical Secondary Standard, Certified Reference Material, Citric acid, meets analytical specification of Ph. Eur., BP, USP, E330, anhydrous, 99.5-100.5% (based on anhydrous substance), 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

Bioactivity: Tricarboxylic acid cycle intermediate; metabolic regulator and urinary alkalinizing agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1,4-Dioxane	303.2	-	140.0	[37]
1,4-Dioxane	308.2	-	195.0	[37]
1,4-Dioxane	313.2	-	280.9	[37]
1,4-Dioxane	318.2	-	328.0	[37]
1,4-Dioxane	323.2	-	360.7	[37]
1,4-Dioxane	328.2	-	394.4	[37]
1,4-Dioxane	333.2	-	422.6	[37]
1-Butanol	288.15	-	131.8	[39]
1-Butanol	291.15	-	149.2	[39]
1-Butanol	294.15	-	169.1	[39]
1-Butanol	297.15	-	191.3	[39]
1-Butanol	299.15	-	207.8	[39]
1-Butanol	301.15	-	225.8	[39]
1-Butanol	303.15	-	245.4	[39]
1-Butanol	305.15	-	266.7	[39]
1-Butanol	307.15	-	288.6	[39]
1-Butanol	309.15	-	315.1	[39]
1-Butanol	311.15	-	342.6	[39]
1-Butanol	313.15	-	373.1	[39]
1-Butanol	315.15	-	406.4	[39]
1-Butanol	317.15	-	442.0	[39]
1-Butanol	319.15	-	482.7	[39]
1-Butanol	323.15	-	578.5	[39]
1-Butanol	327.15	-	690.9	[39]
1-Butanol	330.15	-	799.4	[39]
1-Butanol	333.15	-	918.4	[39]
1-Propanol	293.7	-	970.6	[38]
1-Propanol	303.3	-	985.9	[38]
1-Propanol	313.4	-	1007.5	[38]
Acetone	288.15	-	154.8	[39]
Acetone	291.15	-	177.5	[39]
Acetone	294.15	-	203.4	[39]
Acetone	297.15	-	232.9	[39]
Acetone	299.15	-	255.1	[39]
Acetone	301.15	-	279.4	[39]
Acetone	303.15	-	305.9	[39]
Acetone	305.15	-	335.5	[39]
Acetone	307.15	-	367.3	[39]
Acetone	309.15	-	403.0	[39]
Acetone	311.15	-	441.6	[39]
Acetone	313.15	-	485.4	[39]
Acetone	315.15	-	533.2	[39]
Acetone	317.15	-	586.9	[39]
Acetone	319.15	-	646.4	[39]
Acetone	323.15	-	787.5	[39]
Acetone	327.15	-	967.0	[39]
Acetone	330.15	-	1135.1	[39]
Acetone	333.15	-	1341.8	[39]
Acetonitrile	303.2	-	178.0	[37]
Acetonitrile	308.2	-	209.0	[37]
Acetonitrile	313.2	-	235.0	[37]
Acetonitrile	318.2	-	242.0	[37]
Acetonitrile	323.2	-	260.0	[37]
Acetonitrile	328.2	-	286.0	[37]
Acetonitrile	333.2	-	300.0	[37]
Ethanol	288.15	-	1080.5	[39]
Ethanol	291.15	-	1152.2	[39]
Ethanol	293.7	-	1086.3	[38]
Ethanol	294.15	-	1221.4	[39]
Ethanol	297.15	-	1291.3	[39]
Ethanol	299.15	-	1332.7	[39]
Ethanol	301.15	-	1373.4	[39]
Ethanol	303.15	-	1413.7	[39]
Ethanol	303.2	-	175.0	[37]
Ethanol	303.3	-	1200.0	[38]
Ethanol	305.15	-	1453.5	[39]
Ethanol	307.15	-	1489.9	[39]
Ethanol	308.2	-	218.0	[37]
Ethanol	309.15	-	1522.7	[39]
Ethanol	311.15	-	1555.8	[39]
Ethanol	313.15	-	1583.9	[39]
Ethanol	313.2	-	239.0	[37]
Ethanol	313.4	-	1255.5	[38]
Ethanol	315.15	-	1611.7	[39]
Ethanol	317.15	-	1628.4	[39]
Ethanol	318.2	-	263.0	[37]
Ethanol	319.15	-	1652.5	[39]
Ethanol	323.15	-	1682.4	[39]
Ethanol	323.2	-	307.0	[37]
Ethanol	327.15	-	1700.2	[39]
Ethanol	328.2	-	387.2	[37]
Ethanol	330.15	-	1704.8	[39]
Ethanol	333.15	-	1700.7	[39]
Ethanol	333.2	-	449.5	[37]
Isopropanol	303.2	-	40.4	[37]
Isopropanol	308.2	-	73.8	[37]
Isopropanol	313.2	-	135.0	[37]
Isopropanol	318.2	-	167.0	[37]
Isopropanol	323.2	-	223.0	[37]
Isopropanol	328.2	-	271.2	[37]
Isopropanol	333.2	-	321.0	[37]
Tetrahydrofuran	303.2	-	349.0	[37]
Tetrahydrofuran	308.2	-	365.2	[37]
Tetrahydrofuran	313.2	-	375.0	[37]
Tetrahydrofuran	318.2	-	417.0	[37]
Tetrahydrofuran	323.2	-	486.1	[37]
Tetrahydrofuran	328.2	-	590.2	[37]
Tetrahydrofuran	333.2	-	637.3	[37]
Toluene	288.15	-	109.2	[39]
Toluene	291.15	-	115.7	[39]
Toluene	294.15	-	122.5	[39]
Toluene	297.15	-	129.7	[39]
Toluene	299.15	-	134.6	[39]
Toluene	301.15	-	139.8	[39]
Toluene	303.15	-	145.1	[39]
Toluene	305.15	-	150.6	[39]
Toluene	307.15	-	156.3	[39]
Toluene	309.15	-	162.1	[39]
Toluene	311.15	-	168.2	[39]
Toluene	313.15	-	174.5	[39]
Toluene	315.15	-	181.0	[39]
Toluene	317.15	-	187.7	[39]
Toluene	319.15	-	194.6	[39]
Toluene	323.15	-	209.1	[39]
Toluene	327.15	-	224.7	[39]
Toluene	330.15	-	237.3	[39]
Toluene	333.15	-	250.4	[39]
Water	278.15	-	1065.5	[40]
Water	283.15	-	1181.3	[40]
Water	288.15	-	1320.0	[40]
Water	288.15	-	1323.6	[39]
Water	291.15	-	1409.7	[39]
Water	293.15	-	1444.8	[40]
Water	293.7	-	1484.3	[38]
Water	294.15	-	1499.6	[39]
Water	297.15	-	1590.6	[39]
Water	298.15	-	1618.4	[40]
Water	299.15	-	1654.8	[39]
Water	301.15	-	1719.5	[39]
Water	303.15	-	1867.9	[40]
Water	303.15	-	1793.5	[39]
Water	303.2	-	653.0	[37]
Water	303.3	-	1885.0	[38]
Water	305.15	-	1865.3	[39]
Water	307.15	-	1937.8	[39]
Water	308.15	-	2044.8	[40]
Water	308.2	-	857.0	[37]
Water	309.15	-	2009.5	[39]
Water	311.15	-	2089.5	[39]
Water	313.15	-	2147.4	[40]
Water	313.15	-	2170.0	[39]
Water	313.2	-	1060.0	[37]
Water	313.4	-	2179.6	[38]
Water	315.15	-	2249.0	[39]
Water	317.15	-	2331.6	[39]
Water	318.2	-	1382.0	[37]
Water	318.65	-	2353.8	[40]
Water	319.15	-	2419.9	[39]
Water	322.2	-	2408.1	[38]
Water	323.15	-	2478.0	[40]
Water	323.15	-	2596.5	[39]
Water	323.2	-	1725.0	[37]
Water	327.15	-	2785.5	[39]
Water	328.15	-	2613.2	[40]
Water	328.2	-	1938.0	[37]
Water	330.15	-	2934.4	[39]
Water	333.1	-	2715.6	[38]
Water	333.15	-	2792.3	[40]
Water	333.15	-	3087.9	[39]
Water	333.2	-	2203.0	[37]
Water	338.15	-	3016.8	[40]

Molecule 3D descriptors

Descriptor	Value
PMI1	418.2170
PMI2	908.4791
PMI3	1059.0118
NPR1	0.3949
NPR2	0.8579
RadiusOfGyration	2.4917
InertialShapeFactor	0.0021
Eccentricity	0.9187
Asphericity	0.2367
SpherocityIndex	0.3723
PBF	0.7289