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C0759

Sigma-Aldrich

Citric acid

99%

Synonym(s):

2-Hydroxy-1,2,3-propanetricarboxylic acid, 2-Hydroxypropan-1,2,3-tricarboxylic acid

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About This Item

Linear Formula:
HOC(COOH)(CH2COOH)2
CAS Number:
Molecular Weight:
192.12
Beilstein:
782061
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39021801
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Assay

99%

form

crystals

expl. lim.

8 %, 65 °F

pKa (25 °C)

(1) 3.13, (2) 4.76, (3) 6.40

pKa 

(1) 3.13, (2) 4.76, (3) 6.4

mp

153-159 °C (lit.)

solubility

water: soluble 383 g/L at 25 °C

SMILES string

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

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

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General description

Citric acid is a natural component widely usedin many industrial applications such as chelation, buffering, pH adjustment,and derivatization. It can also be used as a reagent in condensation, acidcatalysis, cycloaddition, deprotection, and decarboxylation reactions.

Application

Citric acid can be used as a reactant to synthesize:
  • Trialkyl citrates via sulfuric acid-catalyzed esterification with aliphatic alcohols C2-C5.
  • Biodegradable thermoset polymer via catalyst-free polycondensation reaction.
It can also be used as a catalyst to synthesize amido alkyl naphthols by reacting 2-naphthols, aldehydes, and amides/ureas.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A method for decalcification with citric acid.
Foschini MP and Muzzi L.
Biotechnic & Histochemistry, 68(1), 42-45 (1993)
Determination of citric acid in fats.
Ohlson R, et al.
Journal of the American Oil Chemists' Society, 45(6), 475-476 (1968)
Wheat straw hemicellulose films as affected by citric acid.
Azeredo HMC, et al.
Food Hydrocolloids, 50 (2015)
Factors affecting the successful cryopreservation of honey bee (Apis mellifera) spermatozoa.
Hopkins BK and Herr C.
Apidologie, 41(5), 548-556 (2010)
Trisha Pasricha et al.
Endoscopy, 46(7), 614-618 (2014-05-23)
Capsule endoscopy is an attractive alternative to colorectal cancer screening by conventional colonoscopy, but is currently limited by compromised mucosal visibility because of the lack of safe, controlled colonic insufflation. We have therefore developed a novel system of untethered, wireless-controlled

Articles

Citrate is one of many cell culture components that affects the performance of serum-free, protein-free and animal protein-free cell culture systems used for biomanufacturing heterologous proteins such as monoclonal antibodies.

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