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Showing Compound Citric acid (FDB012586)

Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2020-09-17 15:42:22 UTC
Primary IDFDB012586
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitric acid
DescriptionCitric acid (citrate) is a weak tricarboxylic acid that is formed in the tricarboxylic acid cycle. In humans citric acid is produced endogenously or it may be introduced with diet, with citrus fruits being a key source. Citrate is produced by all aerobic organisms, from microbes to humans. Citrate is formed in the TCA cycle via the enzyme known as citrate synthase, which catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for aconitase and is converted into aconitic acid. Some bacteria (notably E. coli) can produce and consume citrate internally as part of their TCA cycle, but are unable to use it as food because they lack the enzymes required to import it into the cell. Citrate has a number of biological roles in humans. In particular, it can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis. Citrate can also acts as a signalling molecule. High concentrations of cytosolic citrate can inhibit phosphofructokinase, the catalyst of a rate-limiting step of glycolysis. Inhibition of glycolysis has been shown to suppress tumor growth in a number of animal models ( PMID: 28674429). Citrate is also a vital component of bone, helping to regulate the size of apatite crystals. Urinary citrate levels can be used to identify a number of disorders. Indeed urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in characterizing bone diseases such as osteoporosis (PMID 12957820). The secretory epithelial cells of the prostate gland of humans and other animals possess a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. Testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes (PMID 12198595). In addition to its biological roles and endogenous production, citrate is obtained from many other sources and used in many applications. Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. The concentrations of citric acid in citrus fruits range from 5 mM for oranges and grapefruits to 300 mM in lemons and limes. However, these values vary within species depending upon the cultivar and the circumstances in which the fruit was grown. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. Citric acid is also used as an acidulant in creams, gels, and liquids. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Altered levels of citric acid have been found to be associated with maple syrup urine disease, primary hypomagnesemia, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism.
CAS Number77-92-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Foods

Fruits and vegetables:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-fb757b614278bb898b542014-09-20View Spectrum
GC-MSCitric acid, 4 TMS, GC-MS Spectrumsplash10-0002-0941000000-c310fda0e6a19bf6ae40Spectrum
GC-MSCitric acid, 4 TMS, GC-MS Spectrumsplash10-0002-0941000000-f1dfda3e9abc7cfb6b2aSpectrum
GC-MSCitric acid, 4 TMS, GC-MS Spectrumsplash10-006t-0952000000-ba3a1a80815f65afd05cSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0951000000-48857e9baebe16d9fc8dSpectrum
GC-MSCitric acid, 4 TMS, GC-MS Spectrumsplash10-00di-9531000000-b6fd7d038634694f0873Spectrum
GC-MSCitric acid, 4 TMS, GC-MS Spectrumsplash10-00di-0593000000-b193bbba8c0cefdfe42aSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0941000000-c310fda0e6a19bf6ae40Spectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0941000000-f1dfda3e9abc7cfb6b2aSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-006t-0952000000-ba3a1a80815f65afd05cSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0951000000-48857e9baebe16d9fc8dSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-00di-9531000000-b6fd7d038634694f0873Spectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-00di-0593000000-b193bbba8c0cefdfe42aSpectrum
GC-MSCitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0941000000-573230e47a4efb1e36a5Spectrum
Predicted GC-MSCitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002k-6900000000-d1a61a52f6efdec3101aSpectrum
Predicted GC-MSCitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02ib-6019300000-6d5ebea10441c6d4149aSpectrum
Predicted GC-MSCitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitric acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2900000000-956001b034bbc0b7da962012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000l-9100000000-55e34e2c1616942fd4f22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9000000000-7b8be3e90a4daf85f04a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0911200000-af80d22f720facc4813a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-6f4fedbb19821898fb222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8eff68ab89f7ce2262be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fsi-0019300000-b370c4c3dd656c8eb7292012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0912100000-05e8ceb6dd97f7b9af982012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-e4b67745443c48a63bd62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-92536abec982e0a653a02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-35772df08490f451d8282012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-35856cc258368d13e1ff2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01p9-9500000000-9a502981b0a9e1ea35ad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-ed0c86b90e1f4966d0252012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4r-9000000000-b8a975c2d639d8c91afb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-2900000000-30970a4250098e1486582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-a587dddf188152c5d7b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01p9-9500000000-9a502981b0a9e1ea35ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-42a125e9128ce21bd7852017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9000000000-b8a975c2d639d8c91afb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03di-0900000000-32af4c1bf55ea1563e532017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9000000000-6f4fedbb19821898fb222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-8eff68ab89f7ce2262be2017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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).
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).