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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

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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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)
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
M L Martins et al.
Food additives and contaminants, 19(6), 568-574 (2002-06-04)
Patulin and citrinin are mycotoxins produced by certain fungi mainly belonging to Penicillium and Aspergillus and may be detected in mouldy fruits and fruit products. The data presented here refer to the simultaneous occurrence of patulin and citrinin in 351
Liliana J G Silva et al.
Foods (Basel, Switzerland), 10(1) (2020-12-31)
Citrinin (CIT) deserves attention due to its known toxic effects in mammalian species and its widespread occurrence in food commodities, often along with ochratoxin A, another nephrotoxic mycotoxin. Human exposure, a key element in assessing risk related to food contaminants
Yishan Yang et al.
Fungal biology, 116(2), 225-233 (2012-02-01)
FlbA (fluffy low brlA expression), a regulator of the G protein signalling (RGS) pathway, has been implicated in the control of hyphal development, sporulation, mycotoxin/pigment production in many kinds of filamentous fungi and yeasts. In the current study, a FlbA-like
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