Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Furylfuramide

Furylfuramide

Furylfuramide structure

Furylfuramide 

structure
  • CAS No:

    3688-53-7

  • Formula:

    C11H8N2O5

  • Chemical Name:

    Furylfuramide

  • Synonyms:

    2-Furanacetamide,α-[(5-nitro-2-furanyl)methylene]-;2-Furanacrylamide,α-2-furyl-5-nitro-;α-[(5-Nitro-2-furanyl)methylene]-2-furanacetamide;Furylfuramide;2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide;AF 2 (preservative);Furylamide;AF 2;2-(2-Furyl)-3-(5-nitrofuryl)acrylamide;NSC 44973

Description

orange crystalline solid


Af-2 appears as bright orange crystals. (NTP, 1992)


Af-2 appears as bright orange crystals. (NTP, 1992)

Furylfuramide Basic Attributes

248.19200

248.19

DTXSID9020033

Reddish-orange needles

2932190090

Characteristics

115.19000

3.03020

Af-2 appears as bright orange crystals. (NTP, 1992)

1.453g/cm3

151-152 °C

459.6ºC at 760mmHg

231.8ºC

less than 0.1 mg/mL at 70° F (NTP, 1992)

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Isomerization of cis to trans form of furylfuramide has been shown to occur in the presence of a variety of biological reducing agents.

Hydrophobic. Insoluble in water.

Amides and Imides

A nitrated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Safety Information

Stable. Hydrophobic.

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 FURYLFURAMIDE (6 total), please visit the HSDB record page.

Flash point data for this compound are not available but it is probably combustible. (NTP, 1992)

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|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 FURYLFURAMIDE (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/

Toxicity

INDUCTION OF HISTOPATHOLOGICAL CHANGES IN LIVER DUE TO ADMIN OF 0.06% 4-(DIMETHYLAMINO)AZOBENZENE IN DIET TO 2 MONTHS OLD RATS WAS ALMOST COMPLETELY INHIBITED BY CONCURRENT ADMIN OF 0.2% 2-(2-FURYL)-3-(5-NITRO-2-FURYL)ACRYLAMIDE.|WHEN RHIZOME JUICE OF GINGER, ZINGIBER OFFICINALE, WAS ADDED TO SOLN OF AF2, MUTAGENESIS WAS MARKEDLY INCR. AS RESULT OF COMPONENT FRACTIONATION OF GINGER JUICE, IT WAS FOUND THAT 6-GINGEROL WAS A POTENT MUTAGEN. HOWEVER, GINGER JUICE ALSO CONTAINED ANTI-MUTAGENIC COMPONENT(S) AGAINST 6-GINGEROL. IT IS SUGGESTED THAT 6-GINGEROL COMPONENT MAY BE MUTAGENICALLY ACTIVATED BY PRESENCE OF AF2.|ANTIMUTAGENIC EFFECTS OF CINNAMALDEHYDE ON MUTAGENESIS BY CHEM AGENTS WERE INVESTIGATED IN ESCHERICHIA COLI WP2 UVRA- TRPE-. WHEN ADDED TO AGAR MEDIUM, IT REDUCED NUMBER OF TRP+ REVERTANTS INDUCED BY FURYLFURAMIDE.

LD50 Fisher rat, oral, 340 mg/kg|LD50 ICR/Jcl mouse, female, oral, 475 mg/kg|LD50 Donryu rat, oral, 1554 mg/kg

Drug Information

Following an oral dose of 1.3 mg/kg bw (14)C-AF-2 to rats, 83% of the radioactivity was excreted in the feces and 21% in the urine within 48 hr ... .

AF 2 WAS REDUCED TO THE CORRESPONDING RADICAL ANION BY XANTHINE OXIDASE, LIPOYL DEHYDROGENASE, DT-DIAPHORASE, OR LIVER MICROSOMES IN THE PRESENCE OF AN ELECTRON DONOR.|AFTER ORAL ADMIN OF 3 MG/KG DOSES OF 2-(2-FURYL)-3-(5-NITRO-2-FURYL)ACRYLAMIDE IN RATS IT WAS MAINLY METABOLIZED IN SMALL INTESTINE. PERMEABILITY OF SMALL INTESTINE TO METABOLITES WAS LESS THAN THAT OF PARENT COMPD. XANTHINE OXIDASE WAS INVOLVED IN METAB.|AFTER ORAL ADMIN OF AF-2 TO RABBITS A METABOLITE WAS IDENTIFIED AS 2-(BETA-CARBOXYPROPIONYL)-3-(5-METHYLTHIO-2-FURYL)ACRYLAMIDE BY ITS MASS, IR & NMR SPECTRUM DATA. A SECOND METABOLITE THOUGHT TO BE CIS-TRANS ISOMER OF THE ABOVE WAS IDENTIFIED CONSIDERING ITS UV & MASS SPECTRAL DATA & BEHAVIOR ON TLC.|GENETIC ACTIVITY OF AF-2 IN BACTERIA & YEAST RAPIDLY DISAPPEARED IN PRESENCE OF RAT LIVER MICROSOMAL FRACTION (S9 MIX). INCUBATION WITH S9 MIX EVEN FOR 10 MINUTES AT 37 °C WAS SUFFICIENT FOR COMPLETE INACTIVATION. ACTIVATION IS APPARENTLY NECESSARY FOR GENOTOXIC EFFECT. ACTIVATION STEP MAY INVOLVE REDUCTION OF NITROFURAN TO AN AMINO GROUP. MOST CULTURED CELL SYSTEMS, SUCH AS BACTERIA, YEAST, NEUROSPORA, MAMMALIAN CELLS & HUMAN LYMPHOCYTES, CAN PROBABLY BRING ABOUT THIS REDUCTION. RAPID DISAPPEARANCE OF GENETIC ACTIVITY OF AF-2 IN PRESENCE OF RAT LIVER HOMOGENATE SUGGESTS THAT RAT LIVER MICROSOMES MAY FURTHER METABOLIZE THE REDUCTION PRODUCTS TO INACTIVE FORMS.|For more Metabolism/Metabolites (Complete) data for FURYLFURAMIDE (7 total), please visit the HSDB record page.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)|Carcinogens

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

...HIGHLY MUTAGENIC & CARCINOGENIC.|AF-2 induced a dose-related increase of chromatid aberrations in cultured human lymphocytes and unscheduled DNA synthesis in cultured human fibroblasts. No effect of AF-2 on unscheduled DNA synthesis was seen in fibroblasts from a xeroderma pigmentosum patient. ... This compound induced sister chromatid exchanges in a human lymphoblastoid cell line ... .|Fibroblasts from xeroderma pigmentosum patients, but not from ataxia telangiectasia patients, were clearly more sensitive to AF-2 toxicity than normal human fibroblasts. These finding are consistent with data on bacteria which indicate that AF-2 lesions are repaired by the same pathway as are lesions induced by ultra-violet radiation, but not by the same pathway as those induced by X-rays ... .|In a descriptive epidemiological study in Japan ... examined the correlation in 12 geographic districts between estimated per-caput consumption of AF-2 and dietary fat (reportedly based on a national nutritional surveY) in 1968 and the proportional increase in age-adjusted breast cancer mortality rates from 1969 to 1974. There was an apparently strong positive correlation of the breast cancer variable with each of the estimated intakes of animal fat and AF-2, with each analysis controlled (presumably) for the effect of the other factor. (No information was given about the method of estimating per-caput AF-2 intake, nor about possible confounding effects of other factors ... upon these correlation analyses. Further, the brief time lapse allowed between exposure and cancer death ... may not be etiologically appropriate.)

Furylfuramide Use and Manufacturing

Methods of Manufacturing

AF-2 was first synthesized in 1958. It can be made by the reaction of 5-nitrofurfural with the potassium salt of 2-furfuryl acetic acid in acetic anhydride and treatment of the resulting cmpd with sulfur dichloride to form an acid chloride, which is then heated with ammonia ... .|Prepared by the condensation of 5-nitro-2-furancarboxaldehyde with 2-furanacetic acid followed by chlorination and amination.

Uses

Furylfuramide is a synthetic nitrofuran derivative widely used as a food additive and was investigated for possible carcinogenicity.

Analytical methods for the determination of AF-2 in food preparations are based on colorimetric methods ... The recovery of 10-80 mg/kg in fish sausage was better than 95%.|LSC and measurement of radioactivity by TLC have been used to determine AF-2 in biological fluids ... .

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:248.19
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:248.04332136
Monoisotopic Mass:248.04332136
Topological Polar Surface Area:115
Heavy Atom Count:18
Complexity:376
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.