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C1017

Sigma-Aldrich

Citrinin

from Penicillium citrinum, ≥98% (HPLC)

Synonym(s):

(3R,4S)-8-Hydroxy-3,4,5-Trimethyl-6-Oxo-4,6-Dihydro-3H-Isochromene-7-Carboxylic Acid, 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C13H14O5
CAS Number:
518-75-2
Molecular Weight:
250.25
Beilstein:
5282243
EC Number:
208-257-2
MDL number:
MFCD00006912
UNSPSC Code:
12352200
PubChem Substance ID:
24892302

biological source

Penicillium citrinum

Quality Level

200

Assay

≥98% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

C[C@H]1OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@@H]1C

InChI

1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

InChI key

CQIUKKVOEOPUDV-IYSWYEEDSA-N

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General description

Citrinin is a mycotoxin from Penicillium citrinin that comprises a quinone methide component.

Application

Citrinin has been used as:
  • a standard for calibration curve preparation for citrinin quantification Monascus purpureus ATCC 36928
  • an internal standard in thin layer chromatography (TLC) for characterizing the citrinin from Aspergillus and Penicillium strains
  • standard to characterize citrinin for rotten apples TLC

Biochem/physiol Actions

Citrinin is a predominant contaminant in agriculture supplies and food. It exhibits genotoxic, embryotoxic, and teratogenic properties. It is hepatonephrotoxin and a potent mycotoxin in rice grains.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301 + H311 + H331 - H351

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M R Bragulat et al.
Letters in applied microbiology, 47(4), 286-289 (2009-02-26)
To assess the ability of fungi isolated from grapes to produce patulin and citrinin. A total of 446 Aspergillus isolates belonging to 20 species and 101 Penicillium isolates were inoculated in Czapek yeast extract agar and yeast extract sucrose agar
Effect of dissolved oxygen concentration on red pigment and citrinin production by Monascus purpureus ATCC 36928
Brazilian Journal of Chemical Engineering, 25, 247-253 (2008)
Li-Chuan Hsu et al.
Journal of agricultural and food chemistry, 60(32), 7880-7885 (2012-07-28)
Monascus species have traditionally been used in Asian food, with rice as their fermentation substrate. Red mold rice (RMR) contains citrinin, a nephrotoxic agent capable of exerting oxidative stress and cellular apoptosis. We investigated the components in RMR that could
Maja Segvić Klarić et al.
Archives of toxicology, 86(1), 97-107 (2011-07-09)
The aim of this study was to establish the involvement of calcium signalling in genotoxicity, apoptosis and necrosis evoked by ochratoxin A (OTA) and citrinin (CTN) alone or in combination in porcine kidney PK15 cells. Cell proliferation test (MTT) and
Vanesa Gimena Lourdes Zachetti et al.
Bioelectrochemistry (Amsterdam, Netherlands), 91, 37-43 (2013-02-19)
An amperometric biosensor based on horseradish peroxidase (EC1.11.1.7,H2O2-oxide-reductases) to determine the content of citrinin mycotoxin in rice samples is proposed by the first time. The method uses carbon paste electrodes filled up with multi-walled carbon nanotubes embedded in a mineral
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