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C1017

Sigma-Aldrich

Citrinin

from Penicillium citrinum, ≥98% (HPLC), powder, mycotoxin

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
NACRES:
NA.77

Product Name

Citrinin, from Penicillium citrinum, ≥98% (HPLC)

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

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Certificates of Analysis (COA)

Lot/Batch Number
089M4111V
14190408
039M4033V
118M4076V
108M4104V

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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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