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citric acid

Chemical Structure

General Material Information

Preferred name citric acid
Trivial Name Citric acid
Short Description 1,2,3-propanetricarboxylic acid, 2-hydroxy-
Formula C6 H8 O7
CAS Number 77-92-9
Deleted CAS Number 1192555-95-5
FEMA Number 2306
ECHA Number 201-069-1
FDA UNII XF417D3PSL
Nikkaji Number J2.824J
Beilstein Number 0782061
MDL MFCD00011669
COE Number 20
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 218 citric acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 77-92-9 ; CITRIC ACID
Synonyms
  • 3-carboxy-3-hydroxypentane-1,5-dioic acid
  • citretten
  • citric acid - technical grade
  • citric acid (anhydrous, liquid)
  • citric acid >98.0%(T)
  • citric acid anhydrous fine granular
  • citric acid anhydrous granular
  • citric acid anhydrous granular FCC
  • citric acid anhydrous granular USP
  • citric acid anhydrous granular, natural
  • citric acid anhydrous powder
  • citric acid anhydrous USP/EP/JP
  • citric acid FCC anhydrous
  • citric acid solution
  • citrosol 502
  • citrosol 503
  • 2-hydroxy-1,2,3-propane tricarboxylic acid
  • 2-hydroxypropane tricarboxylic acid
  • 2-hydroxypropane-1,2,3-tricarboxylic acid
  • 2-hydroxytricarballylic acid
  • beta- hydroxytricarboxylic acid
  • 1,2,3-propanetricarboxylic acid, 2-hydroxy-
  • 1,3-propanetricarboxylic acid, 2-hydroxy-
  • 2-hydroxypropane-1,2,3-tricarboxylic acid
  • 1,2,3-Propanetricarboxylic acid, 2-hydroxy-
  • 2-Hydroxy-1,2,3-propanetricarboxylic acid
  • Aciletten
  • Citro
  • Hydrocerol A
  • Chemfill
  • 3-Carboxy-3-hydroxypentane-1,5-dioic acid
  • F 0001 (polycarboxylic acid)
  • Uro-trainer
  • E 330
  • Suby G
  • NSC 112226
  • NSC 30279
  • NSC 626579
  • Celenex 3P6
  • 2-Hydroxy-1,2,3-propanetricarboxyic acid
  • 2-Hydroxypropan-1,2,3-tricarboxylic acid
  • INS 330
  • FE 2
  • F 4020
  • Grindsted Pro Tex TR 100
  • Citric acid monoglyceride
  • Monoglyceride citrate
  • Jet Setter
  • EL 4
  • EL 4 (polycarboxylic acid)
  • Cellborn SC-C
  • KK 120
  • BioLink Acidifier
  • TBA 80
  • PAS 33
  • 8: PN: WO2017048620 SEQID: 13 claimed sequence
  • F 3500
  • C 1949
  • 3-Hydroxy-3-carboxy-1,5-pentanedioic acid
  • 3-Hydroxy-pentane-1,3-5-trioic acid
  • 3-Carboxy-3-hydroxy-pentanedioic acid
  • Liquinat L 50
  • SH 74
  • EMPROVE Essential Ph Eur, BP,JP,USP, E 330, FCC
  • 3-Hydroxy-3-carboxypentanedioic acid
  • MeSH ID: D019343
  • 32: PN: CN118717671 SEQID: 106 claimed protein

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-hydroxypropane-1,2,3-tricarboxylic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:77-92-9
Pubchem (cid):311
Pubchem (sid):134972805
Publications by PubMed
Effect of pretreatments on extraction of pigment from marigold flower.
Identifying flavor preference subgroups. Genetic basis and related eating behavior traits.
Acidic Organic Compounds in Beverage, Food, and Feed Production.
Integration of metabolomics and subcellular organelle expression microarray to increase understanding the organic acid changes in post-harvest citrus fruit.
Impact of roasting time on the sensory profile of arabica and robusta coffee.
Taste loss in hospitalized multimorbid elderly subjects.
New insights into Lactococcus lactis diacetyl- and acetoin-producing strains isolated from diverse origins.
Genetic analysis of chemosensory traits in human twins.
Elucidating the formation pathway of the off-flavor compound 6-propylbenzofuran-7-ol.
The effectiveness of antibrowning dip treatments to reduce after-cooking darkening in potatoes.
Identification and analysis of the metabolic functions of a high-salt-tolerant halophilic aromatic yeast Candida etchellsii for soy sauce production.
Co-mapping studies of QTLs for fruit acidity and candidate genes of organic acid metabolism and proton transport in sweet melon (Cucumis melo L.).
The effect of cocoa fermentation and weak organic acids on growth and ochratoxin A production by Aspergillus species.
Identification and characterization of genes related to the production of organic acids in yeast.
Enhancement of retronasal odors by taste.
Identification of the medicinal off-flavor compound formed from ascorbic acid and (E)-hex-2-enal.
Effect of cassava starch coating on quality and shelf life of fresh-cut pineapple (Ananas comosus L. Merril cv "Pérola").
Citrate uptake in exchange with intermediates in the citrate metabolic pathway in Lactococcus lactis IL1403.
Reconciling sensory cues and varied consequences of avian repellents.
Chemical and instrumental approaches to cheese analysis.
Evaluation of natural antimicrobials on typical meat spoilage bacteria in vitro and in vacuum-packed pork meat.
Chitosan coating improves retention and redispersibility of freeze-dried flavor oil emulsions.
The role of transient receptor potential vanilloid-1 on neural responses to acids by the chorda tympani, glossopharyngeal and superior laryngeal nerves in mice.
Evaluation of the effect of upper complete denture on gustatory and olfactory senses.
Taste disorders and oral evaluation in patients undergoing allogeneic hematopoietic SCT.
High-temperature natural antioxidant improves soy oil for frying.
Effect of tenderizers combined with organic acids on Escherichia coli O157:H7 thermal resistance in non-intact beef.
Production of fresh Cheddar cheese curds with controlled postacidification and enhanced flavor.
Modeling and experimental studies on intermittent starch feeding and citrate addition in simultaneous saccharification and fermentation of starch to flavor compounds.
Microbiological, chemical, and sensory characteristics of Swiss cheese manufactured with adjunct Lactobacillus strains using a low cooking temperature.
Potentiation of taste and extract stimuli in conditioned flavor preference learning.
The sensory interactions of organic acids and various flavors in ramen soup systems.
Relationship between physical properties and sensory attributes of carbonated beverages.
Phenotypic and genotypic analysis of amino acid auxotrophy in Lactobacillus helveticus CNRZ 32.
Food color, flavor, and conditioned avoidance among red-winged blackbirds.
Elementary mode analysis to study the preculturing effect on the metabolic state of Lactobacillus rhamnosus during growth on mixed substrates.
Effect of citric acid and glycine addition on acrylamide and flavor in a potato model system.
Sweetener/sweetness-induced changes in flavor perception and flavor release of fruity and green character in beverages.
On-line MS/MS monitoring of acrylamide generation in potato- and cereal-based systems.
Chemesthesis and taste: evidence of independent processing of sensation intensity.
Descriptive sensory analysis of broiler breast fillets marinated in phosphate, salt, and acid solutions.
Quantitative taste evaluation of total enteral nutrients.
Sour taste preferences of children relate to preference for novel and intense stimuli.
'Thermal taste' predicts higher responsiveness to chemical taste and flavor.
Severe hypotension during hemofiltration in an uremic patient with metabolic alkalosis.
Changes in physicochemical characteristics and volatile constituents of strawberry (Cv. Cigaline) during maturation.
Age-associated increases in intensity discrimination for taste.
Conditioned acceptance and preference but not altered taste reactivity responses to bitter and sour flavors paired with intragastric glucose infusion.
The relation between saliva flow after different stimulations and the perception of flavor and texture attributes in custard desserts.
II. Glutamine and glutamate.
Sweet and sour preferences during childhood: role of early experiences.
Ethanol flavor preference conditioned by intragastric carbohydrate in rats.
Development of a CE method to analyze organic acids in dairy products: application to study the metabolism of heat-shocked spores.
Citrate metabolism by Enterococcus faecalis FAIR-E 229.
An opioid receptor antagonist, naltrexone, does not alter taste and smell responses in humans.
Organic acids and volatile flavor components evolved during refrigerated storage of kefir.
Clinical validation of the Helikit: a 13C urea breath test used for the diagnosis of Helicobacter pylori infection.
Factors affecting the perception of naturalness and flavor strength in citrus drinks.
Control of flavor development in wine during and after malolactic fermentation by Oenococcus oeni.
Increased flavor acceptance and preference conditioned by the postingestive actions of glucose.
Relation between saliva flow and flavor release from chewing gum.
Kinetic analysis of yeast inactivation by high pressure treatment at low temperatures.
Flavor preferences conditioned by intragastric infusions of dilute polycose solutions.
Microbial biocatalysis in the generation of flavor and fragrance chemicals.
Flavor preference produced by intragastric polycose infusions in rats using a concurrent conditioning procedure.
Clinical evaluation of a citric acid inhaler for smoking cessation.
Changes in taste and flavor in aging.
Preference of Old World monkeys for amino acids and other gustatory stimuli: the influence of monosodium glutamate.
Parabrachial gustatory neural responses to monosodium glutamate ingested by awake rats.
Development of a citric acid aerosol as a smoking cessation aid.
Influence of the sense of taste on broiler chick feed consumption.
Flavor preferences in malnourished Mexican infants.
[Intermediate moisture foods: polysaccharide and protein gels].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00158
HMDB (The Human Metabolome Database):HMDB00094
FooDB:FDB012586
YMDB (Yeast Metabolome Database):YMDB00086
Export Tariff Code:2918.14.0000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View
FAO:CITRIC ACID
FAO:Citric acid
Formulations/Preparations:
•anticoagulant citrate dextrose solution, anticoagulant citrate phosphate dextrose solution, citric acid syrup, & effervescent salts. •grades of purity: usp; reagent; monohydrate grade. •grades: both hydrous (hydrated) and anhydrous, technical, chemically pure, united states pharmacopeia, food chemical codex. •citric acid for pharmaceutical use: not 5% water; not >0.05% ash; not >0.001% heavy metals; not > 0.0003% as. hydrous citric acid may contain up to 8.8% water •liquid citric acid is commercially available in a variety of concentrations with 50% ww being most common. grades are available that vary in appearance, purity, and color.

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 192.1241607666
Melting Point 152 to 154°C @ 760 mm Hg
Boiling Point 309 to 310°C @ 760 mm Hg
Flash Point TCC Value 110 °C TCC
logP (o/w) -1.64 est
Solubility
water, 592000 mg/L @ 20 °C (exp) Yes

Organoleptic Properties

Odor Type: Odorless
Odor strength none
General comment At 100.00 %. odorless
Flavor Type: Acidic
acidic
General comment Strong acidic

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 37/38 - Irritating to respiratory system and skin.
R 41 - Risk of serious damage to eyes.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 3000 mg/kg
Oyo Yakuri. Pharmacometrics. Vol. 43, Pg. 561, 1992.

intraperitoneal-mouse LD50 903 mg/kg
Toxicology. Vol. 62, Pg. 203, 1990.

intravenous-mouse LD50 42 mg/kg
GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 94, Pg. 65, 1948.

oral-mouse LD50 5040 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES MUSCULOSKELETAL: OTHER CHANGES
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 25, 1971.

intravenous-rabbit LD50 330 mg/kg
LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 94, Pg. 65, 1948.

oral-rabbit LDLo 7000 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Industrial and Engineering Chemistry. Vol. 15, Pg. 628, 1923.

intraperitoneal-rat LD50 290 mg/kg
Toksikologicheskii Vestnik. Vol. (5), Pg. 9, 1994.

Dermal Toxicity:
subcutaneous-rat LD50 5500 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES MUSCULOSKELETAL: OTHER CHANGES
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 25, 1971.

subcutaneous-mouse LD50 2700 mg/kg
MUSCULOSKELETAL: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 25, 1971.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
acidulants, sequestrants, antioxidant synergists, flavoring agents
Recommendation for citric acid usage levels up to:
not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 29
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 2.000003.00000
beverages(nonalcoholic): 2.000003.00000
beverages(alcoholic): 800.0000020000.00000
breakfast cereal: 0.100000.10000
cheese: 0.400000.90000
chewing gum: 10000.0000025400.00000
condiments / relishes: 0.400000.80000
confectionery froastings: 0.300001.00000
egg products: 0.600000.60000
fats / oils: 0.500000.80000
fish products: 0.300000.40000
frozen dairy: 1.000003.00000
fruit ices: 1.000002.00000
gelatins / puddings: 174.00000210.00000
granulated sugar: --
gravies: 1.000002.00000
hard candy: 950.000001000.00000
imitation dairy: 2.000002.00000
instant coffee / tea: 5.000005.00000
jams / jellies: 2.000006.00000
meat products: 0.800000.90000
milk products: 0.800001.00000
nut products: --
other grains: 0.400000.40000
poultry: 1.000001.00000
processed fruits: 13.0000016.00000
processed vegetables: 0.500001.00000
reconstituted vegetables: 33.0000033.00000
seasonings / flavors: --
snack foods: 0.400001.00000
soft candy: 2.0000014.00000
soups: 0.200000.20000
sugar substitutes: --
sweet sauces: 3.000003.00000

Safety references

European Food Safety Authority (EFSA) reference(s):

Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf

Review of substances/agents that have direct beneficial effect on the environment: mode of action and assessment of efficacy
View page or View pdf

Scientific Opinion on the safety and efficacy of citric acid when used as a technological additive (acidity regulator) for all animal species
View page or View pdf

Scientific Opinion on the safety and efficacy of citric acid when used as a technological additive (preservative) for all animal species
View page or View pdf

Safety assessment of the active substances citric acid and sodium hydrogen carbonate for use in active food contact materials
View page or View pdf

Re-evaluation of acetic acid, lactic acid, citric acid, tartaric acid, mono- and diacetyltartaric acid, mixed acetic and tartaric acid esters of mono- and diglycerides of fatty acids (E 472a-f) as food additives
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):77-92-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :311
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
2-hydroxypropane-1,2,3-tricarboxylic acid
Chemidplus:0000077929
EPA/NOAA CAMEO:hazardous materials
RTECS:77-92-9