Sterigmatocystin

324.28

324.28

233-158-6

5F95211S5Z

201423|204985

DTXSID2021280

Pale-yellow crystals

29329990

78.13000

1.62

yellow powder

1.2842 (rough estimate)

246 °C (decomp)

382.63°C (rough estimate)

6℃

1.4800 (estimate)

Insol in strong aq alkali; sparingly sol in most organic solvents; readily sol in dimethylsulfoxide, chloroform, pyridine|7138 MG/100 ML CHLOROFORM, 1815 MG/100 ML PYRIDINE|In water, 1.44 mg/L at 25 °C (est)

2-8°C

1.39E-13mmHg at 25°C

Oral-Rat  LD50 120  mg/kg; Oral-Mouse LD50: > 800 mg/kg

Flammable, spicy and irritating smoke emitted from the fire

Henry's Law constant = 2.83X10-12 atm-cu m/mol at 25 °C (est)

163 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]

Forms deep-yellow color with aq sodium hydroxide and dark green-brown color with sulfuric acid; emits orange-red fluorescence in ultra-violet light|Hydroxyl radical reaction rate constant = 2.79X10-10 cu cm/molec-sec at 25 °C (est)|Ozone radical rate constant = 5.7X10-17 cu cm/molec-sec (est)

III

6.1(b)

UN 3462 6.1/PG 3

3

25-40-36-20/21/22-11

36/37-45-16

LV1750000

T,Xn,F

Treasury is low temperature, ventilated, dry; stored separately from food raw materials

P281-P301 + P310

H301-H351

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for STERIGMATOCYSTIN (6 total), please visit the HSDB record page.

HAMASAKI T; CHEMISTRY OF STERIGMATOCYSTIN; MAIKOTOKISHIN (TOKYO) 12: 5 (1980). A REVIEW WITH 6 REFERENCES ON THE CHEMISTRY, MICROBIOLOGIC BIOSYNTHESIS, AND CARCINOGENICITY OF STERIGMATOCYSTIN.

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 197 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for STERIGMATOCYSTIN (9 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

highly toxic

LD50 Monkey (vervet) ip 32 mg/kg bw dissolved in dimethylsulfoxide.|LD50 Rat (male) oral (10 days) 166 mg/kg bw when the cmpd was dissolved in dimethylformamide.|LD50 Rat (female) oral (10 days) 120 mg/kg bw, when it was dissolved in wheat-germ oil.|LD50 Rat (male) ip 60-65 mg/kg bw, depending on the solvent used.|LD50 Mouse oral 800 mg/kg

FUNGAL SOURCE: BIPOLARIS SOROKINIANA SACCARDO IN SHOROK (SHOEM), ASPERGILLUS AURANTIO-BRUNNEUS (ATKINS, HINDSON, AND RUSSELL), ASPERGILLUS QUADRILINEATUS (THOM & RAPER), ASPERGILLUS USTUS BAINIER (THOM & CHURCH), ASPERGILLUS VARIECOLOR, ALSO AN INTERMEDIATE IN BIOSYNTHESIS OF AFLATOXINS BY ASPERGILLUS PARASITICUS AND ASPERGILLUS FLAVUS.|Sterigmatocystin has been found as a natural contaminant on green coffee beans and on wheat(1).|CHEESES RIPENING IN WAREHOUSES & MOLDED WITH ASPERGILLUS VERSICOLOR WERE EXAMINED FOR STERIGMATOCYSTIN. NINE OF 39 CHEESE SAMPLES CONTAINED STERIGMATOCYSTIN IN THE SURFACE LAYER IN CONCN RANGING 5-600 UG/KG.|... /Sterigmatocystin/ has been produced in the lab from cultures of Aspergillus versicolor (vuillemin) tiraboshi, from Aspergillus nidulans (eidam) wint ... of 16 cultures of Aspergillus versicolor found on country-cured hams, 10 were found to be capable of producing sterigmatocystin in culture on three types of lab media. ... sterigmatocystin was also identified in salami inoculated with two strains of Aspergillus versicolor; 1-2 mg/kg were found on the casing and 0.1 mg/kg in the interior.|For more Natural Pollution Sources (Complete) data for STERIGMATOCYSTIN (6 total), please visit the HSDB record page.

...THE FDA DID NOT FIND STERIGMATOCYSTIN IN THEIR ANALYSIS OF OVER 500 U.S. CEREAL GRAIN SAMPLES IN SURVEYS CONDUCTED IN 1974-1975.|CHEESES RIPENING IN WAREHOUSES & MOLDED WITH ASPERGILLUS VERSICOLOR WERE EXAMINED FOR STERIGMATOCYSTIN. NINE OF 39 CHEESE SAMPLES CONTAINED STERIGMATOCYSTIN IN THE SURFACE LAYER IN CONCN RANGING 5-600 UG/KG.|Cultures of Aspergillus versicolor found on country-cured hams were found to be capable of producing sterigmatocystin in cultures of laboratory media(1). It was identified in salami inoculated with two strains of Aspergillus versicolor(1).

In rats given a single ip injection of 6.4 mg/animal (14)C-sterigmatocystin in DMSO, 5.6% of the activity was found in the urine, 67% in the feces and GI tract and 11% in the liver after 12 hours. These levels declined slightly after 24 hr. In fasted or non-fasted rats given 1.4 mg/animal (3)H-sterigmatocystin orally, the highest activity after 16 hr was found in the feces and GI tract; lesser amounts were found in the urine, blood, expired air, liver and kidneys.

In Vervet monkeys the major urinary metabolite was identified as sterigmatocystin-beta-d-glucuronide, which accounted for 75% of the oral dose administered.|Sterigmatocystin was covalently bound to calf thymus DNA by incubation with phenobarbital-induced rat liver microsomes. The adduct was identified as 1,2-dihydro-2-(N7-guanyl)-1-hydroxysterigmatocystin. The structure and stereochemistry of this adduct indicated that the exo-sterigmatocystin-1,2-oxide was the metabolite that reacted with DNA, and the quantitative yield of adduct indicated that this metabolite was a major product of the in vitro metabolism of sterigmatocystin.|The species sensitivity to sterigmatocystin toxicity was in the order: monkey greater than rat greater than mouse. It was postulated that these differences were due to species differences in liver sterigmatocystin distribution, sterigmatocystin 2,3-epoxide formation from sterigmatocystin and drug-metabolizing enzymes in the liver microsome.|/Sterigmatocystin is/ activated by /a/ human P450 enzyme, CYP3A4. /From table/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/OTHER TOXICITY INFORMATION/ ... Sterigmatocystin-treated cells exhibited an absence of P53-mediated G1 arrest with induction of MDM2 at 12 and 24 hours of treating time. Long term treatment with Sterigmatocystin enhanced dominantly the development of intestinal metaplasia, and of precancerous lesions of gastric mucosa in Helicobacter pylori-infected Mongolian gerbils. The accumulations of P53 nucleotide substitutions in the H. pylori-infected monkeys were increased as the score of gastric atrophy increased, nevertheless no mutations were noted in the H. pylori-uninfected monkeys.|/OTHER TOXICITY INFORMATION/ ... DNA agarose gel electrophoresis results showed the characteristic "ladder" pattern of apoptosis in human peripheral blood lymphocytes (HPBLs) treated with sterigmatocystin (ST), deoxynivalenol (DON) and aflatoxin G1 (AFG1). Flow cytometric DNA analysis revealed that typical subdiploid peaks of apoptosis in DNA histogram could be seen in all groups treated with the three mycotoxins. Significant time-effect and dose-effect relationships were found between the apoptosis rates and treatment time as well as concentrations of the three mycotoxins.

Sterigmatocystin

It has been produced in the lab from cultures of Aspergillus versicolor (vuillemin) tiraboshi, from Aspergillus nidulans (eidam) wint ... of 16 cultures of Aspergillus versicolor found on country-cured hams, 10 were found to be capable of producing sterigmatocystin in culture on three types of lab media. ... sterigmatocystin was also identified in salami inoculated with two strains of Aspergillus versicolor; 1-2 mg/kg were found on the casing and 0.1 mg/kg in the interior.|It is produced by ... Penicillium luteum ...|Sterigmatocystin ... is elaborated by ... Aspergillus rugulosus ...|... Sterigmatocystin ... /is/ a xanthone derivative. ...With a bisdihydrofuran ring system in the molecule.|Biochemically sterigmatocystin ... /is a/ biosynthetic precursor to the aflatoxins ... sterigmatocystin and aflatoxin induce similar but not identical toxicological effects.

...ASSAY /DESCRIBED/ FOR THE QUANTITATIVE DETERMINATION OF AS LITTLE AS 0.0025 UG STERIGMATOCYSTIN IN GRAIN AND OIL SEEDS USING THIN-LAYER CHROMATOGRAPHY (TLC)... A TLC METHOD IN WHICH ALUMINUM CHLORIDE IS SPRAYED ONTO THE DEVELOPED PLATE HAS DETECTED 30 UG/KG...IN SPIKED WHEAT OR OTHER GRAIN SAMPLES. A TLC METHOD HAS ALSO BEEN DEVELOPED FOR SCREENING FUNGAL EXTRACTS AND FOR THE ANALYSIS OF GROUNDNUTS FOR THREE MYCOTOXINS INCL STERIGMATOCYSTIN...WITH A LIMIT OF DETECTION OF 0.01 UG.|AN ANALYTICAL METHOD BY HIGH PERFORMANCE THIN-LAYER CHROMATOGRAPHY IS DESCRIBED FOR THE SIMULTANEOUS DETERMINATION OF 13 MYCOTOXINS (FOOD CONTAMINANTS & SUSPECTED CARCINOGENS) INCL STERIGMATOCYSTIN. BY USING IN SITU SCANNING OF THE HPTLC PLATE, DETECTION LIMITS IN THE LOW NANOGRAM RANGE WERE OBTAINED BY UV-VISIBLE ABSORPTION (REFLECTANCE MODE) AND IN THE LOW PICOGRAM RANGE BY FLUORESCENCE WITH A RELATIVE STANDARD DEVIATION OF 0.7-2.2% IN THE NANOGRAM RANGE.|... TOXIC STERIGMATOCYSTIN AND DIHYDROSTERIGMATOCYSTIN WERE DETERMINED IN CONTAMINATED FOOD BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY. THE DETECTION LIMIT WAS APPROXIMATELY 10 NG.|Method: AOAC 973.38; Procedure: thin layer chromatographic method; Analyte: sterigmatocystin; Matrix: barley and wheat; Detection Limit: not provided.

Food Contaminant -> MYCOTOXIN; -> JECFA Functional Classes|Polyketides [PK] -> Aflatoxins and related substances [PK10]

Food Contaminant -> MYCOTOXIN;