ChemicalBook > CAS DataBase List > CITRININ

CITRININ

Product Name
CITRININ
CAS No.
518-75-2
Chemical Name
CITRININ
Synonyms
CIT;ANTIMYCIN;CTRO;NSC 186;CITRININ;KIAA0949;Cltrinin;Citriain;CITRININE;Cytrinine
CBNumber
CB3190931
Molecular Formula
C13H14O5
Formula Weight
250.25
MOL File
518-75-2.mol
More
Less

CITRININ Property

Melting point:
175°C (dec.)
alpha 
D18 -37.4° (c = 1.15 in alc.)
Boiling point:
313.38°C (rough estimate)
Density 
1.37
refractive index 
1.4560 (estimate)
Flash point:
2℃
storage temp. 
2-8°C
solubility 
≤2mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide
form 
Crystalline Powder or Flakes
pka
1.52±0.60(Predicted)
color 
Yellow
Merck 
13,2351
BRN 
5282243
Stability:
Hygroscopic
CAS DataBase Reference
518-75-2(CAS DataBase Reference)
IARC
3 (Vol. 40, Sup 7) 1987
EPA Substance Registry System
Citrinin (518-75-2)
More
Less

Safety

Hazard Codes 
T
Risk Statements 
23/24/25-40-36/37/38
Safety Statements 
26-36/37/39-45-22-7/9
RIDADR 
UN 3462 6.1/PG 3
WGK Germany 
3
RTECS 
DJ2275000
HazardClass 
6.1(a)
PackingGroup 
II
HS Code 
29419090
Hazardous Substances Data
518-75-2(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (mg/kg): 35, 67 i.p. (Ambrose, De Eds)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C1017
Product name
Citrinin
Purity
from
Packaging
5mg
Price
$227
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB4500213
Product name
Anti-CTRO antibody produced in rabbit
Purity
affinity isolated antibody
Packaging
100μg
Price
$506
Updated
2024/03/01
Sigma-Aldrich
Product number
35410
Product name
Citrinin solution
Purity
100 μg/mL in acetonitrile, analytical standard
Packaging
1ml
Price
$835
Updated
2024/03/01
Alfa Aesar
Product number
J64007
Product name
Citrinin, 98%
Packaging
5mg
Price
$139
Updated
2021/12/16
Cayman Chemical
Product number
11320
Product name
Citrinin
Purity
≥98%
Packaging
1mg
Price
$36
Updated
2024/03/01
More
Less

CITRININ Chemical Properties,Usage,Production

Description

Citrinin is a mycotoxin that has been found in Monascus and has diverse biological activities. It is active against S. aureus, methicillin-resistant S. aureus (MRSA), rifampicin-resistant S. aureus, and vancomycin-resistant E. faecium (MICs = 1.95, 3.9, 0.97, and 7.81 μg/ml, respectively), as well as the pathogenic yeast C. neoformans (MIC = 3.9 μg/ml). It is cytotoxic to a variety of cells in vitro, including bovine kidney cells and mice embryonic stem cells. Citrinin (30 μM) induces reactive oxygen species (ROS) production, mitochondrial membrane potential loss, and apoptosis in HepG2 cells, effects that can be blocked by the antioxidant resveratrol. In contrast, citrinin reduces glutamate-induced excitotoxicity in primary rat cortical neurons at concentrations ranging from 0.1 to 1,000 nM and inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 cells at 0.625 to 40 μM. It is toxic to brine shrimp larvae (LD50 = 96 μg/ml), as well as to rats and mice with oral LD50 values of 50 and 87-105 mg/kg, respectively. It induces reproductive abnormalities in male mice and toxic effects in the liver, kidney, heart, and gastrointestinal tracts of various animals. Citrinin has been found in stored cereal grains, as well as beans, fruit, and herbs.

Chemical Properties

Antimycin (A3C26H36N2O9) and (Antimycin A1) C28H40N2O9 are crystalline solids.

Chemical Properties

yellow crystalline powder or flakes

Uses

Antibiotic substance produced by a white spore aspergilus which has been placed under the species name Aspergillus niveus. Also produced in small quantities by Penicillium citrinum.

Uses

antibacterial

Uses

Citrinin is a quinonemethine mycotoxin produced by diverse fungi including Aspergillus and Penicillium. Citrinin has been extensively investigate, and is a potent nephrotoxin with hepatoxic and teratogenic activity. Citrinin is the causative agent of Balkan nephropathy and yellow rice fever in humans. At the molecular level, citrinin exhibits a range of effects including free radical damage to DNA and disruption of mitochondrial membrane-bound enzymic activities and structural integrity. Specifically, citrinin is an inhibitor of NADH dehydrogenase in the mitochondrial electron transport chain and this action is responsible for recent reports of citrinin's apoptotic activity.

Definition

ChEBI: (-)-citrinin is a citrinin. It has a role as a Penicillium metabolite. It is an enantiomer of a (+)-citrinin.

General Description

Citrinin is a hepato-nephrotoxic mycotoxin. It can be produced by several filamentous fungi genera of Monauscus, Aspergillus, and Penicillium, which is commonly found as a contaminant in stored grains, foods, feedstuffs and also in biological fluids.

Potential Exposure

Specific uses for antimycin A were not found, however, antimycin A1, and antimycin A3 are reported to be antibiotic substances produced by streptomyces for use as a fungicide, possible insecticide and miticide. Registered as a pesticide in the U.S.

in vitro

previous study found that exposure of hek293 cells to citrinin led to an arrest of cell cycle g2/m in a concentration-dependent increase. citrinin treatment could also elevate the expression levels of p53 and p21 proteins, yet attenuate the signals of phosphorylated cell division cycle 2. moreover, treating hek293 with citrinin could increase both the value of mitotic index and the population of cells, indicating that arrest of citrinin -induced cell cycle occurred mainly during the mitotic phase [1].

in vivo

previous study showed that citrinin acted as a nephrotoxin in all tested animal species, but its acute toxicity varied in different species. the 50% lethal dose for ducks is 57 mg/kg; for chickens it is 95 mg/kg; and for rabbits it is 134 mg/kg. in murine kidneys, citrinin could also synergistically act with ochratoxin a to depress rna synthesis [2].

storage

+4°C

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

References

[1] chang ch, yu fy, wu ts, wang lt, liu bh. mycotoxin citrinin induced cell cycle g2/m arrest and numerical chromosomal aberration associated with disruption of microtubule formation in human cells. toxicol sci. 2011 jan;119(1):84-92.
[2] j. w. bennett and m. klich. mycotoxins. clin.microbiol.rev. 16(3), 497-516 (2003).

CITRININ Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

CITRININ Suppliers

SIGMA-RBI
Tel
--
Fax
--
Country
Switzerland
ProdList
6896
Advantage
91
Alexis Corporation
Tel
--
Fax
--
Email
alexis-ch@alexis-corp.ch
Country
Switzerland
ProdList
3599
Advantage
74
More
Less

View Lastest Price from CITRININ manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
CITRININ 518-75-2
Price
US $50.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000
Release date
2024-03-25
Hebei Weibang Biotechnology Co., Ltd
Product
Citrinin 518-75-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-30
Hebei Yanxi Chemical Co., Ltd.
Product
Citrinin 518-75-2
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-10-18

518-75-2, CITRININRelated Search:


  • ANTIMYCIN
  • CIT
  • CITRININ
  • CITRININ, PENICILLIUM CITRINUM
  • 4,6-DIHYDRO-8-HYDROXY-3,4,5-TRIMETHYL-6-OXO-3H-2-BENZOPYRAN-7-CARBOXYLIC
  • 4,6-DIHYDRO-8-HYDROXY-3,4,5-TRIMETHYL-6-OXO-3H-2-BENZOPYRAN-7-CARBOXYLIC ACID
  • (3r,4s)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3h-2-benzopyran-7-carbox
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R,4S)-
  • CITRININE
  • Antimycin, Citrinin
  • (3R)-3α,4β,5-Trimethyl-6-oxo-8-hydroxy-3,4-dihydro-6H-2-benzopyran-7-carboxylic acid
  • (3R)-4,6-Dihydro-8-hydroxy-3α,4β,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
  • (3R,4S)-3,4,5-Trimethyl-6-oxo-8-hydroxy-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
  • Citrinin,98%
  • CITRININ(RG)
  • Citrinin,4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
  • Anti-CTRO antibody produced in rabbit
  • CTRO
  • KIAA0949
  • Rho-interacting
  • Cltrinin
  • Citrinin, 100ppm
  • MeleaMycin, AntiMycin, Monascidin A
  • Citrinin solution
  • (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
  • ,(3r-trans)-
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
  • 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3h-2-benzopyran-7-carboxylicaci
  • 6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-(3r-trans)-3h-2-benzopyran-7-carboxylicaci
  • 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
  • Citriain
  • citrinin,antimycin
  • 3,4-dihydro-8-hydroxy-3,4,5-trimethyl-6H-6-oxobenzo(c)pyran-7-carboxylic acid
  • CITRININ FROM PENICILLIUM CITRINUM
  • Cytrinine
  • (-)-2&szlig
  • -(4-iodophenyl)nortropane (nor-&szlig
  • -Carbomethoxy-3&szlig
  • (-)-Citrini
  • NSC 186
  • CITRININ USP/EP/BP
  • TIANFUCHEM--High purity CITRININ factory price
  • 13C13]-Citrinin-10 μg/mL in ACN
  • (-)-Citrini
  • (3R,4S)-8-Hdroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
  • Citrinin in acetonitrile
  • CITRININ(RG) 5mg
  • 518-75-2
  • C13H14O5
  • antibiotic
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Active Pharmaceutical Ingredients