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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/REAXYS Number:
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

functional group

carboxylic acid
hydroxyl

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

signalword

Warning

hcodes

H319,H335

Hazard Classifications

Eye Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000405315
0000404613
0000403898
0000403897
0000359621

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Assay of Ornithine Decarboxylase and Spermidine/Spermine N1-acetyltransferase Activities.
Hyvonen MT, et al.
Bio-protocol, 4(22) (2014)
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
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)
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