AFCDB: Citric acid (FDB012586)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:15 UTC

Update date

2020-09-17 15:42:22 UTC

Primary ID

FDB012586

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Citric acid

Description

Citric 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 Number

77-92-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	106 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.3	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.62 m³·mol⁻¹	ChemAxon
Polarizability	15.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H8O7

IUPAC name

2-hydroxypropane-1,2,3-tricarboxylic acid

InChI Identifier

InChI=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 Key

KRKNYBCHXYNGOX-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O

Average Molecular Weight

192.1235

Monoisotopic Molecular Weight

192.02700261

Classification

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:30769 )

Ontology

Foods

Fruits and vegetables:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 37.51%; H 4.20%; O 58.29%	DFC
Melting Point	Mp 153° (anhyd.)	DFC
Boiling Point	Not Available
Experimental Water Solubility	592 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	-1.64	AVDEEF,A (1997)
Experimental pKa	pKa3 6.43 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-002f-9400000000-fb757b614278bb898b54	2014-09-20	View Spectrum
GC-MS	Citric acid, 4 TMS, GC-MS Spectrum	splash10-0002-0941000000-c310fda0e6a19bf6ae40	Spectrum
GC-MS	Citric acid, 4 TMS, GC-MS Spectrum	splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a	Spectrum
GC-MS	Citric acid, 4 TMS, GC-MS Spectrum	splash10-006t-0952000000-ba3a1a80815f65afd05c	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0951000000-48857e9baebe16d9fc8d	Spectrum
GC-MS	Citric acid, 4 TMS, GC-MS Spectrum	splash10-00di-9531000000-b6fd7d038634694f0873	Spectrum
GC-MS	Citric acid, 4 TMS, GC-MS Spectrum	splash10-00di-0593000000-b193bbba8c0cefdfe42a	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0941000000-c310fda0e6a19bf6ae40	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-006t-0952000000-ba3a1a80815f65afd05c	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0951000000-48857e9baebe16d9fc8d	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-00di-9531000000-b6fd7d038634694f0873	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-00di-0593000000-b193bbba8c0cefdfe42a	Spectrum
GC-MS	Citric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0941000000-573230e47a4efb1e36a5	Spectrum
Predicted GC-MS	Citric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002k-6900000000-d1a61a52f6efdec3101a	Spectrum
Predicted GC-MS	Citric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02ib-6019300000-6d5ebea10441c6d4149a	Spectrum
Predicted GC-MS	Citric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citric acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-2900000000-956001b034bbc0b7da96	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000l-9100000000-55e34e2c1616942fd4f2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000f-9000000000-7b8be3e90a4daf85f04a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0911200000-af80d22f720facc4813a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-6f4fedbb19821898fb22	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-8eff68ab89f7ce2262be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0fsi-0019300000-b370c4c3dd656c8eb729	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0912100000-05e8ceb6dd97f7b9af98	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-e4b67745443c48a63bd6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-92536abec982e0a653a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-35772df08490f451d828	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-35856cc258368d13e1ff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-3900000000-7170fdcb9749e6d6c2fb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-01p9-9500000000-9a502981b0a9e1ea35ad	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000i-9100000000-ed0c86b90e1f4966d025	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4r-9000000000-b8a975c2d639d8c91afb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-2900000000-30970a4250098e148658	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-a587dddf188152c5d7b0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-3900000000-7170fdcb9749e6d6c2fb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01p9-9500000000-9a502981b0a9e1ea35ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-42a125e9128ce21bd785	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-b8a975c2d639d8c91afb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-32af4c1bf55ea1563e53	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-9000000000-6f4fedbb19821898fb22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-8eff68ab89f7ce2262be	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C 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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30769

Phenol-Explorer ID

Not Available

DrugBank ID

DB04272

HMDB ID

HMDB00094

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1000441

SuperScent ID

Not Available

Wikipedia ID

Citric_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	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 inhibitor	50627	An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).	DUKE
anti aphthic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti atherosclerotic	38070	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 bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti calculic			DUKE
anti coagulant	50249	An agent that prevents blood clotting.	DUKE
anti leishmanic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti mutagenic			DUKE
antioxidant	22586	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 seborrheic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
disinfectant	48219	An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hemostat			DUKE
irritant			DUKE
laxative	50503	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
litholytic			DUKE
mycobactericide			DUKE
odontolytic			DUKE
refrigerant	78433	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

Name	Gene Name	UniProt ID
ATP-citrate synthase	ACLY	P53396
Citrate synthase, mitochondrial	CS	O75390
Aconitate hydratase, mitochondrial	ACO2	Q99798
Proto-oncogene tyrosine-protein kinase Src	SRC	P12931
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	CTDSP1	Q9GZU7
Carboxypeptidase B	CPB1	P15086
Adenine phosphoribosyltransferase	APRT	P07741
Ribonuclease pancreatic	RNASE1	P07998
Macrophage migration inhibitory factor	MIF	P14174
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1	HS3ST3A1	Q9Y663
Angiogenin	ANG	P03950
Eosinophil cationic protein precursor	RNASE3	P12724

Pathways

Name	SMPDB Link	KEGG Link
Citric Acid Cycle	SMP00057	map00020
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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).

Citric acid (FDB012586)

Structure for FDB012586 (Citric acid)