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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:
77-92-9
Molecular Weight:
192.12
Beilstein:
782061
EC Number:
201-069-1
MDL number:
MFCD00011669
UNSPSC Code:
12352100
eCl@ss:
39021801
PubChem Substance ID:
329774820
NACRES:
NA.21

Quality Level

200

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
GHS07

Signal Word

Warning

Hazard Statements

H319,H335

Hazard Classifications

Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)
Factors affecting the successful cryopreservation of honey bee (Apis mellifera) spermatozoa.
Hopkins BK and Herr C.
Apidologie, 41(5), 548-556 (2010)
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)
Assay of Ornithine Decarboxylase and Spermidine/Spermine N1-acetyltransferase Activities.
Hyvonen MT, et al.
Bio-protocol, 4(22) (2014)
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