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7H-Furo[3,2-g][1]benzopyran-7-one,4-methoxy-(CAS No. 484-20-8)

7H-Furo[3,2-g][1]benzopyran-7-one,4-methoxy- C12H8O4 (cas 484-20-8) Molecular Structure

484-20-8 Structure

Identification and Related Records

【Name】
7H-Furo[3,2-g][1]benzopyran-7-one,4-methoxy-
【Iupac name】
4-methoxyfuro[3,2-g]chromen-7-one
【CAS Registry number】
484-20-8
【Synonyms】
5-MOP
5-Methoxy-6,7-furanocoumarin
5-Methoxypsoralen
Bergaptan
Bergaptene
Geralen
Heraclin
Majudin
NSC 95437
Psoraderm
【EINECS(EC#)】
207-604-5
【Molecular Formula】
C12H8O4 (Products with the same molecular formula)
【Molecular Weight】
216.20
【Inchi】
InChI=1/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
【InChIKey】
BGEBZHIAGXMEMV-UHFFFAOYSA-N
【Canonical SMILES】
COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
【MOL File】
484-20-8.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline solid
【Density】
1.368 g/cm3
【Melting Point】
190-193 ºC
【Boiling Point】
412.4 °C at 760 mmHg
【Vapour】
5.2E-07mmHg at 25°C
【Refractive Index】
1.635
【Flash Point】
203.2 °C
【Water】
negligible in water
【Solubilities】
negligible in water
【Color/Form】
NEEDLES FROM ALCOHOL; SOLN IN SULFURIC ACID IS YELLOW-GOLD
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:216.18952 [g/mol]
Molecular Formula:C12H8O4
XLogP3-AA:2.3
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:1
Exact Mass:216.042259
MonoIsotopic Mass:216.042259
Topological Polar Surface Area:48.7
Heavy Atom Count:16
Formal Charge:0
Complexity:325
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Ring Count:3
Effective Rotor Count:1
Conformer Sampling RMSD:0.6
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R43
【Safety Statements 】
36/37
【Safety】
Questionable carcinogen. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
【Cleanup Methods】
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/
【Transport】
UN 1759
【Other Preventative Measures】
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/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
【Specification】

Crystalline Solid
usageEng:Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic
Safety Statements:36/37
36/37:Wear suitable protective clothing and gloves
【Disposal Methods】
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/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

...ISOLATED FROM OIL OF BERGAMOT FROM CITRUS BERGAMIA RISSO, AURANTIODIAE. ISOLATION FROM FAGARA XANTHOXYLOIDES LAM, RUTACEAS. SYNTHESIS.
5-Methoxypsoralen was first synthesized in 1937 ... by the condensation of 3,4,6-triacetoxycoumaran with ethyl sodium formyl acetate and methylation of the resulting product. Other synthetic routes have been described which use 6-formyl-7-hydroxy-5-methoxycoumarin-7-O-acetic acid ... the methyl ester of 2,6-dioxy-4-methoxybenzoic acid ... and 5-allyloxy-7-hydroxycoumarin ... as precursors.
【Usage】
Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
【Therapeutic Uses】
5-Methoxypsoralen, in combination with UVA, is commonly used as a photochemotherapeutic agent for the treatment of psoriasis ... .
【Biomedical Effects and Toxicity】
MICRONIZED BERGAPTEN IN CAPSULES WAS ABSORBED SLOWLY BY VOLUNTEERS (TIME TO MAX SERUM CONCN 3.2 HR; ELIM HALF-TIME ABOUT 1 HR). WHEN INJECTED IV INTO RABBITS, ELIM HALF-TIME 1-2 MIN (ALPHA-PHASE) & 15 MIN (BETA-PHASE).
5-METHOXYPSORALEN SHOWED A HIGH BINDING AFFINITY TO SERUM PROTEINS & 98-99% WAS PROTEIN BOUND. ITS HIGH BINDING AFFINITY RESULTED IN HIGHER TISSUE CONCN. IN THE EPIDERMIS, IT APPEARED TO BE BOUND TO INDEPENDENT & NONINTERACTING SITES. [ARTUC M ET AL; BR J DERMATOL 101 (6): 669 (1979)] PubMed Abstract
ENRICHMENT IN EPIDERMIS OF 5-METHOXYPSORALEN WAS MEASURED. IT WAS CONCENTRATED BY HUMAN EPIDERMIS & CONCN REACHED WITHIN THE TISSUE WAS 10-500 TIMES HIGHER THAN CONCN OF SUBSTANCE IN SURROUNDING BUFFER. THE PARTITIONING DISTRIBUTION AMONG TISSUE COMPONENTS COULD ACCOUNT FOR ITS BEHAVIOR. [ARTUC M ET AL; ARCH DERMATOL RES 268 (2): 129 (1980)] PubMed Abstract
In young adult Hartley guinea-pigs, a linear relation was found between serum and epidermal concn of 5-methoxypsoralen, and the observed skin phototoxicity correlated with the serum 5-methoxypsoralen concn ... .
Following oral administration of 40 mg 5-methoxypsoralen to healthy male volunteers, absorption was documented by measurement of plasma levels. The plasma concn peaked 2-4 hr after administration and declined to low levels by 8 hr. Distribution to the skin after topical application of 0.15 and 0.0015% 5-methoxypsoralen was evident from photosensitization, persisting up to 8 hr, to 366 nm UV light with an irradiance of 22 mW/sq cm 2 hr after administration. Minute amt of 5-methoxypsoralen were excreted in urine and bile ... .
5-Methoxypsoralen binds to human serum proteins, principally albumin. ... Data on 5-methoxypsoralen binding to low-density lipoproteins suggest that these are the primary vehicle for intracellular transport of 5-methoxypsoralen ... .

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