| Identification | More | [Name]
CITRININ | [CAS]
518-75-2 | [Synonyms]
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
ANTIMYCIN
CIT
CITRININ
CITRININ, PENICILLIUM CITRINUM
(3r,4s)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3h-2-benzopyran-7-carbox
(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
3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R,4S)- | [EINECS(EC#)]
208-257-2 | [Molecular Formula]
C13H14O5 | [MDL Number]
MFCD00006912 | [Molecular Weight]
250.25 | [MOL File]
518-75-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Antimycin (A3C26H36N2O9) and (Antimycin
A1) C28H40N2O9 are crystalline solids. | [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) | [Fp ]
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) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S22:Do not breathe dust .
S7/9:Keep container tightly closed and in a well-ventilated place . | [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) |
| Hazard Information | Back Directory | [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. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed. As
first aid for pulmonary edema, a doctor or authorized paramedic
may consider administering a drug or other inhalation
therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | [Description]
Citrinin is a mycotoxin that has been found in Monascus and has diverse biological activities.1,2,3,4 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).2 It is cytotoxic to a variety of cells in vitro, including bovine kidney cells and mice embryonic stem cells.4 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.3 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.4 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.2,4 It induces reproductive abnormalities in male mice and toxic effects in the liver, kidney, heart, and gastrointestinal tracts of various animals.4 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]
antibacterial | [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]
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. | [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]
Store at -20°C, stored under nitrogen | [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). |
|
|