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791725

Sigma-Aldrich

Citric acid

anhydrous, free-flowing, Redi-Dri™, ACS reagent, ≥99.5%

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Synonym(s):
2-Hydroxy-propane-1,2,3-tricarboxylic acid
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
PubChem Substance ID:
329768287
NACRES:
NA.21

grade

ACS reagent
anhydrous

Quality Level

200

product line

Redi-Dri™

Assay

≥99.5%

form

crystals

quality

free-flowing

expl. lim.

8 %, 65 °F

impurities

Substances carbonizable by hot sulfuric acid, passes test

ign. residue

≤0.02%

pKa 

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

mp

153-159 °C (lit.)

anion traces

chloride (Cl-): ≤0.001%
oxalate (C2O42-): passes test (limit about 0.003%)
phosphate (PO43-): ≤0.001%
sulfate (SO42-): ≤0.002%

cation traces

Fe: ≤3 ppm
Pb: ≤2 ppm

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 also called 2-hydroxy-propane-1,2,3-tricarboxylic acid, is a component of the tricarboxylic acid cycle in all organisms. Industrial production of citric acid use fungal, yeast and citrus fruit as the major source. Aspergillus niger is majorly used for citric acid production by fermentation Manganese inhibits fermentative production of citric acid Oral supplementation of citric acid promotes tricarboxylic acid cycle and oxidative phosphorylation in mitochondria, attenuating physical fatigue.

Application

Citric acidhas been used as a component of citrate buffer and Fe-free sauton′s medium. It has been used in hybridization chain reaction buffer for preequilibration of coverslips for testes sections.

Legal Information

Redi-Dri™ is a trademark of Sigma-Aldrich Co. LLC
Redi-Dri is a trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319 - H335

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

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A comprehensive roadmap of murine spermatogenesis defined by single-cell RNA-seq
Green CD, et al.
Developmental Cell, 46(5), 651-667 (2018)
Biochemical studies of citric acid production and accumulation by Aspergillus niger mutants
Gupta S and Sharma CB
World Journal of Microbiology & Biotechnology, 18(5), 379-383 (2002)
Biotechnological production of citric acid
Max B, et al.
Brazilian Journal of Microbiology, 41(4), 862-875 (2010)
Effects of citric acid and L-carnitine on physical fatigue
Sugino T, et al.
Journal of Clinical Biochemistry and Nutrition, 41(3), 224-230 (2007)
Methylene blue exerts a neuroprotective effect against traumatic brain injury by promoting autophagy and inhibiting microglial activation
Zhao M, et al.
Molecular Medicine Reports, 13(1), 13-20 (2016)
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