Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2018-05-29 00:59:18 UTC
Primary IDFDB012586
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitric acid
DescriptionOccurs in the free state in lemons, currants, beetroot etc. and the seeds and juices of many flowers and plants. Commercially produced by large-scale fermentation of sugars using the mould Aspergillus nigus. Constituent of fruit drinks, pharmaceutical syrups. Flavouring ingredient. Primary function as an acid, acidity regulator, antioxidant, preservative and sequestrant. One of the most widely used food additives. Its clean taste makes it applicable in soft drinks, sugar confectionery, preserves, soups and sauces Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks. Citric acid is found in many foods, some of which are dill, chanterelle, walnut, and sapodilla.
CAS Number77-92-9
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxy-1,2,3-propanetricarboxylic acidChEBI
2-Hydroxytricarballylic acidChEBI
3-Carboxy-3-hydroxypentane-1,5-dioic acidChEBI
CitronensaeureChEBI
e330ChEBI
H3CitChEBI
Anhydrous citric acidKegg
Citric acid anhydrousKegg
2-Hydroxy-1,2,3-propanetricarboxylateGenerator
2-HydroxytricarballylateGenerator
3-Carboxy-3-hydroxypentane-1,5-dioateGenerator
Anhydrous citrateGenerator
Citrate anhydrousGenerator
CitrateGenerator
AcilettenHMDB
beta-HydroxytricarballylateHMDB
beta-Hydroxytricarballylic acidHMDB
ChemfillHMDB
CitracleanHMDB
CitrettenHMDB
CitroHMDB
e 330HMDB
Hydrocerol aHMDB
Kyselina citronovaHMDB
Suby gHMDB
Uro-trainerHMDB
Acid monohydrate, citricHMDB
Monohydrate, citric acidHMDB
Citric acid, anhydrousHMDB
Citric acid monohydrateHMDB
Uralyt uHMDB
1,2,3-Propanetricarboxylic acid, 2-hydroxy- (9CI)biospider
2-hydroxypropane-1,2,3-tricarboxylic acidbiospider
2-Hydroxypropanetricarboxylic acidbiospider
E330db_source
FEMA 2306db_source
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H8O7
IUPAC name2-hydroxypropane-1,2,3-tricarboxylic acid
InChI IdentifierInChI=1S/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)
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC(O)(CC(O)=O)C(O)=O
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
Classification
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 37.51%; H 4.20%; O 58.29%DFC
Melting PointMp 153° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility592 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-1.64AVDEEF,A (1997)
Experimental pKapKa3 6.43 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-c310fda0e6a19bf6ae40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-f1dfda3e9abc7cfb6b2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-006t-0952000000-ba3a1a80815f65afd05cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0951000000-48857e9baebe16d9fc8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9531000000-b6fd7d038634694f0873View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0593000000-b193bbba8c0cefdfe42aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-c310fda0e6a19bf6ae40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-f1dfda3e9abc7cfb6b2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0952000000-ba3a1a80815f65afd05cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0951000000-48857e9baebe16d9fc8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9531000000-b6fd7d038634694f0873View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0593000000-b193bbba8c0cefdfe42aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-573230e47a4efb1e36a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002k-6900000000-d1a61a52f6efdec3101aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02ib-6019300000-6d5ebea10441c6d4149aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2900000000-956001b034bbc0b7da96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000l-9100000000-55e34e2c1616942fd4f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9000000000-7b8be3e90a4daf85f04aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0911200000-af80d22f720facc4813aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-6f4fedbb19821898fb22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8eff68ab89f7ce2262beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fsi-0019300000-b370c4c3dd656c8eb729View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0912100000-05e8ceb6dd97f7b9af98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-e4b67745443c48a63bd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-92536abec982e0a653a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-35772df08490f451d828View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-35856cc258368d13e1ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01p9-9500000000-9a502981b0a9e1ea35adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-ed0c86b90e1f4966d025View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4r-9000000000-b8a975c2d639d8c91afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-2900000000-30970a4250098e148658View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-a587dddf188152c5d7b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0037-0900000000-06dccacb53e75edc8b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02cu-5900000000-bfea9d561968b2670b13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-7900000000-b1d32e4661447b09a017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-1900000000-d074598ec2180f8b600cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k92-3900000000-9917f196271a495d3d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9600000000-513b016c7c951d1e0b12View in MoNA
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-fb757b614278bb898b54View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID305
ChEMBL IDCHEMBL1261
KEGG Compound IDC00158
Pubchem Compound ID311
Pubchem Substance IDNot Available
ChEBI ID30769
Phenol-Explorer IDNot Available
DrugBank IDDB04272
HMDB IDHMDB00094
CRC / DFC (Dictionary of Food Compounds) IDHJD14-D:HJD14-D
EAFUS ID691
Dr. Duke IDCITRIC-ACID
BIGG ID34080
KNApSAcK IDC00007619
HET IDCIT
Flavornet IDNot Available
GoodScent IDrw1000441
SuperScent IDNot Available
Wikipedia IDCitric_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
alpha-amylase inhibitor50627 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).DUKE
anti aphthic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti calculicDUKE
anti coagulant50249 An agent that prevents blood clotting.DUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
disinfectant48219 An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hemostatDUKE
irritantDUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
litholyticDUKE
mycobactericideDUKE
odontolyticDUKE
refrigerant78433 A substance used in a thermodynamic heat pump cycle or refrigeration cycle that undergoes a phase change from a gas to a liquid and back. Refrigerants are used in air-conditioning systems and freezers or refrigerators and are assigned a "R" number (by ASHRAE - formerly the American Society of Heating, Refrigerating and Air Conditioning Engineers), which is determined systematically according to their molecular structure.DUKE
Enzymes
NameGene NameUniProt ID
ATP-citrate synthaseACLYP53396
Citrate synthase, mitochondrialCSO75390
Aconitate hydratase, mitochondrialACO2Q99798
Proto-oncogene tyrosine-protein kinase SrcSRCP12931
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1CTDSP1Q9GZU7
Carboxypeptidase BCPB1P15086
Adenine phosphoribosyltransferaseAPRTP07741
Ribonuclease pancreaticRNASE1P07998
Macrophage migration inhibitory factorMIFP14174
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1HS3ST3A1Q9Y663
AngiogeninANGP03950
Eosinophil cationic protein precursorRNASE3P12724
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).