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6-니트로크리센

6-Nitrochrysene

HCID 24121
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
7496-02-8
표준 SMILES
O=[N+]([O-])c1cc2c3ccccc3ccc2c2ccccc12
InChIKey
UAWLTQJFZUYROA-UHFFFAOYSA-N
분자식
C18H11NO2
평균 분자량
273.3 g/mol
단동위원소 질량
273.07897859

개요

6-Nitrochrysene can cause cancer according to The World Health Organization's International Agency for Research on Cancer (IARC).

이름 및 식별자

우선 이름
6-Nitrochrysene
IUPAC
6-nitrochrysene
현지명
6-니트로크리센
영어명
6-NITROCHRYSENE
분자식
C18H11NO2
분자량
273.29

이름 및 동의어

6-NITROCHRYSENE7496-02-8Chrysene, 6-nitro-DTXSID907545482ZK83O33YNSC-407609RefChem:105092DTXCID2047727626-732-6CHEMBL828586-NITROCHRYSENE (purity)6-Nitrochrysene [Nitroarenes]
이름 더 보기
6-나이트로크리센6-니트로크리센6-나이트로크리센(6-NITROCHRYSENE)6-Nitrochrysene,99%6-Nitrochrysene in toluene84218, 6-Nitrochrysene (purity)6-Nitrochrysene@100 μg/mL in Toluene6-NITROCHRYSENE UNLABELED 50 UG/ML IN TOLUENE
CCRIS 29756-Nitro-chrysene4-Nitrochrysene #NSC 407609BRN 2134652NITROCHRYSENE, 6-SCHEMBL710252UNII-82ZK83O33Y

데이터베이스 식별자

CAS
7496-02-8
PubChem CID
24121
DTXSID
DTXSID9075454
ChEMBL
CHEMBL82858
ChEBI
CHEBI:82351
UNII
82ZK83O33Y

물성

구조 계산 물성

XLogP
5.5
극성 표면적
45.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
21
형식 전하
0
복잡도
405

실험 및 물리화학적 성질

Chemical ClassesCarcinogens
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
Color/Form · 3건

Yellow needles from benzene

Orange-yellow needles

Chrome-red, thick prismatic crystals

SolubilitySlightly soluble in cold ethanol, diethyl ether and carbon disulfide; somewhat more soluble in benzene and acetic acid; soluble in hot nitrobenzene
Boiling Point · 2건

Sublimes without decomposition (NTP, 1992)

Sublimes without decomposition

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point · 2건

408 °F (NTP, 1992)

approximately 215 °C (decomposes)

Vapor Pressure0.00000001 [mmHg]
Physical Description · 2건

Chrome-red thick prismatic crystals or orange-yellow needles (recrystallized from pyridine or xylene). (NTP, 1992)

Yellow, orange-yellow, or chrome red solid; [HSDB]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H302+H312+H332 (76.5%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H350: May cause cancer [Danger Carcinogenicity]

유해성 정보

Regulatory Information · 2건

Hazard Traits - Carcinogenicity

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992)
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS. See Chrysene.
Reactive GroupHydrocarbons, Aromatic
Special Reports · 3건

IARC Monographs on the Evaluation of Carcinogenic Risks to Humans; Diesel and Gasoline Engine Exhausts and Some Nitroarenes (vol 46) p.267-276 (1989). IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Summary available from; as of November 18, 2009: http://monographs.iarc.fr/ENG/Monographs/vol46/volume46.pdf]

화학 및 산업

약리 정보

Mechanism of Action · 2건

The mutant fractions (MF) and mutational specificities in the cII gene /were determined/ in histologically confirmed normal, non-involved and tumor mammary tissues of female transgenic (Big Blue F344 x Sprague-Dawley)F1 rats treated with the environmental pollutant 6-nitrochrysene (6-NC). At 30 days of age, three groups were set up for oral treatment with 6-NC dissolved in trioctanoin, or trioctanoin alone once a week for 8 weeks. Two dose levels of 6-NC (100 and 200 micromol/rat) were selected on the basis of our previous carcinogenicity bioassays with CD rats. The rats were decapitated 32 weeks after the last carcinogen dose. Both incidence and multiplicity of mammary adenocarcinomas were significantly elevated in the high dose (36%, 0.57, P < 0.01) group but at the low dose these outcomes (16%, 0.23, P < 0.1) were not significantly different from those of control rats (3%, 0.03). The MF in normal, non-involved and tumor tissues from the mammary glands of 6-NC-treated rats were comparable. At the high and low doses, respectively (4.8 +/- 2.0, 3.2 +/- 2.1) the MF of 6-NC-treated rats, were significantly higher (P < 0.05) than that observed in control rats (1.2 +/- 0.6). Control mutants consisted primarily of GC --> AT transitions, whereas 6-NC-induced mutants were comprised of several major classes of mutations with GC --> TA, GC --> CG, AT --> GC and AT --> TA as the most prevalent. Further studies indicated that the structures of 6-NC-DNA adducts in the mammary tissue are consistent with the mutational specificities. This is the first report that defines the relationship between carcinogenesis and mutagenesis, as well as between structures of 6-NC-DNA adducts and mutation characteristics in the target organ in vivo.

The environmental pollutant 6-nitrochrysene (6-NC) is a potent carcinogen in several animal models including the rat mammary gland. 6-NC can be activated to intermediates that can damage DNA by simple nitroreduction, ring oxidation, or a combination of ring oxidation and nitroreduction. Only the first pathway (nitroreduction) has been clearly established, and DNA adducts derived from this pathway have been fully characterized in in vitro systems. We also showed previously that the second pathway, ring oxidation leading to the formation of the bay region diol epoxide of 6-NC, is not responsible for the formation of the major DNA adduct in the mammary gland of rats treated with 6-NC. Therefore, ... the validity of the third pathway that involves the combination of both ring oxidation and nitroreduction of 6-NC to form trans-1,2-dihydroxy-1,2-dihydro-6-hydroxylaminochrysene (1,2-DHD-6-NHOH-C) /was explored/ ... 1,2-DHD-6-NHOH-C, N-(deoxyguanosin-8-yl)-6-aminochrysene, and N-(deoxyguanosin-8-yl)-1,2-dihydroxy-1,2-dihydro-6-aminochrysene /were synthesized/. Incubation of 1,2-DHD-6-NHOH-C with calf thymus DNA resulted in the formation of three adducts. Upon LC/MS combined with 1H NMR analyses, the first eluting adduct was identified as 5-(deoxyguanosin-N2-yl)-1,2-dihydroxy-1,2-dihydro-6-aminochrysene [5-(dG-N2-yl)-1,2-DHD-6-AC], the second eluting adduct was identified as N-(deoxyguanosin-8-yl)-1,2-dihydroxy-1,2-dihydro-6-aminochrysene, and the last was identified as N-(deoxyinosin-8-yl)-1,2-dihydroxy-1,2-dihydro-6-aminochrysene ... Among those adducts identified in vitro, only 5-(dG-N2-yl)-1,2-DHD-6-AC is the major DNA lesion detected in the mammary glands of rats treated with 6-NC.

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
EC Number
626-732-6
Nikkaji
J92.343E

물리화학적 성질

녹는점
220 °C · 220 °C (dec.)(lit.)
끓는 점
416.31 °C · 416.31°C (rough estimate)
밀도
1.2123 · 1.2123 (rough estimate)
굴절률
1.48 · 1.4800 (estimate)
저장 조건
2 · 2-8°C
용해도
클로로포름 (약간 용해됨), 에틸아세테이트 (약간 용해됨,초음파처리)
색상
연한 노란색에서 밝은 노란색까지
BRN
2134652 · 2134652
Henry's Law Constant
6.6 · 6.6×102 mol/(m3Pa) at 25℃, HSDB (2015)
EPA
6 · 6-Nitrochrysene (7496-02-8)

화학적 성질

brown powder

WHO; Environmental Health Criteria 229: Selected Nitro- and Nitro-Oxy-Polycyclic Aromatic Hydrocarbons (2003). EHC are designed for scientists and administrators responsible for the establishment of safety standards and regulations and provide basic scientific risk evaluations of a wide range of chemicals and groups of chemicals.[Available from, as of November 18, 2009: http://www.inchem.org/pages/ehc.html]

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 6-Nitrochrysene (7496-02-8) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of September 24, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s121nitr.pdf]

Reactivity Profile6-NITROCHRYSENE reacts with tin and hydrochloric acid in glacial acetic acid. It also reacts with bromine and fuming nitric acid. (NTP, 1992)
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and Categories · 4건

Acute Tox. 4 (76.5%)

Germ cell mutagenicity - Category 2

Carcinogenicity - Category 1B

Carcinogens

Shipment Methods and Regulations · 2건

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/

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/

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1건

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.

Storage Conditions · 1건

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/

Cleanup Methods · 1건

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/

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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.

Disposal Methods · 5건

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/

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": 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": ... 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/

For more Disposal Methods (Complete) data for 6-Nitrochrysene (6 total), please visit the HSDB record page.

Preventive Measures · 5건

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/

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": 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": 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/

For more Preventive Measures (Complete) data for 6-Nitrochrysene (9 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 2건

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/

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+5(SRC), determined from a structure estimation method(2), indicates that 6-nitrochrysene is expected to be immobile in soil(SRC). Volatilization of 6-nitrochrysene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 6-Nitrochrysene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.6X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). A 2.0% mineralization after 2 weeks of incubation with a sediment Mycobacterium sp. inoculum acclimated to pyrene(5) indicates that this compound may not be expected to biodegrade rapidly in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+5(SRC), determined from a structure estimation method(2), indicates that 6-nitrochrysene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.5X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1,500(SRC), from an estimated log Kow of 5.3(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). A 2.0% mineralization after 2 weeks of incubation with a sediment Mycobacterium sp. inoculum acclimated to pyrene(8) indicates that this compound may not be expected to biodegrade rapidly in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 6-nitrochrysene, which has an estimated vapor pressure of 7.6X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 6-nitrochrysene may be removed from the air by wet or dry deposition(SRC). 6-Nitrochrysene does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsIARC Carcinogen - Class 2: International Agency for Research on Cancer classifies chemicals as probable (2a), or possible (2b) human carcinogens.
Effluent Concentrations6-Nitrochrysene was detected in 6 out of 6 airborne samples in air and diesel particulate collected from Baltimore, Maryland at concentrations ranging from 2.0-2368 ng/g(1).
Medical Surveillance · 1건

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 6-nitrochyrsene can be estimated to be 2.9X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 6-nitrochrysene is expected to be immobile in soil.

Atmospheric Concentrations · 1건

URBAN/SUBURBAN: 6-Nitrochrysene was detected in 2 out of 4 airborne samples in the vapor plus particulate phase collected from Houston, Texas between August 26, 1990 - September 5, 1990 (summer) and between September 30, 1990 - November 18, 1990 (fall) at concentrations ranging from 1.5-5.2 pg/cu m(1). 6-Nitrochrysene was detected in an unknown amount of airborne samples in the atmosphere of Baltimore, Maryland in January 2001 at concentrations ranging from 0.27-0.64 pg/cu m and in July 2001 at concentrations ranging from 0.05-0.13 pg/cu m(2). 6-Nitrochrysene was also detected in an unknown amount of airborne samples in the atmosphere of Fort Meade, Maryland in January 2001 at concentrations ranging from 0.20-0.73 pg/cu m and in July 2001 at concentrations ranging from 0.10-0.70 pg/cu m(2).

Human Toxicity Excerpts · 2건

/ALTERNATIVE and IN VITRO TESTS/ ... Using human breast adenocarcinoma MCF-7 cells and immortalized human mammary epithelial MCF-10A cells, ... the effects of 6-nitrochrysene (6-NC) on the expression of p53 protein and its direct downstream target cyclin-dependent kinase inhibitor p21(Cip1) as well as on the cell cycle progression /were determined/. Western blot analysis demonstrated that treatments of MCF-7 and MCF-10A cells with 6-NC for 12, 24 or 48 hr did not increase the level of total p53 protein; however, an increase of p21(Cip1) protein and a commitment increase of G(1) phase were observed in MCF-10A cells but not in MCF-7 cells. Further studies using 1,2-dihydroxy-1,2-dihydro-6-hydroxylaminochrysene (1,2-DHD-6-NHOH-C), the putative ultimate genotoxic metabolite of 6-NC, were conducted and showed a significant induction of p53 (p < 0.05) in MCF-7 cells; however, this effect was not evident in MCF-10A cells, indicating the varied DNA damage responses between the two cell lines. By contrast to numerous DNA damaging agents such as BaP which is known to stimulate p53 expression, the lack of p53 response by 6-NC imply the lack of protective functions mediated by p53 (e.g. DNA repair machinery) after exposure to 6-NC and this may, in part, account for its remarkable carcinogenicity in the mammary tissue.

/OTHER TOXICITY INFORMATION/ ... Treatment of HepG2 cells with 6-nitrochrysene (6-NC) increased the activities of microsomal benzo[a]pyrene hydroxylase, 7-ethoxycoumarin and 7-ethoxyresorufin O-deethylases, cytosolic glutathione S-transferase and N-acetyltransferase, and S9 metabolic activation of 6-NC in the Ames mutagenicity test. Immunoblot and RNA blot analyses revealed that 6-NC induced CYP1A1 protein and mRNA levels in the hepatoma cells. Nuclear transcription assay demonstrated that 6-NC increased the transcription rate of CYP1A1 gene in HepG2 cells. Treatment of human lung carcinoma NCI-H322 cells with 6-NC increased benzo[a]pyrene hydroxylase activity and CYP1A1 protein and mRNA levels. These results demonstrate that 6-NC is an inducer of human CYP1A1 and the induction occurs at a transcriptional level in HepG2 cells ...

Artificial Pollution Sources6-Nitrochrysene's presence in the atmosphere due to reactions of parent polyaromatic hydrocarbons released in various manufacturing processes(1) will result in its direct release to the environment(SRC).
Environmental BiodegradationPURE CULTURE: 6-Nitrochrysene mineralized 2.0% after 2 weeks of incubation with a sediment Mycobacterium sp. inoculum acclimated to pyrene(1).
Carcinogen Classification · 6건

6-Nitrochrysene

Group 2A: Probably carcinogenic to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2014

2012

NB Overall evaluation upgraded to Group 2A with supporting evidence from other relevant data

Environmental Bioconcentration · 1건

An estimated BCF of 1,500 was calculated in fish for 6-nitrochrysene(SRC), using an estimated log Kow of 5.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for 6-nitrochrysene is estimated as 1.5X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 6-nitrochrysene is expected to be essentially nonvolatile from water surfaces(2). 6-Nitrochrysene's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). 6-Nitrochrysene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.6X10-9 mm Hg(SRC), determined from a fragment constant method(3).

안전 데이터

wgk
3
rtecs
GC1930000
risk_code
45-46-20/21/22
hazard_code
T
safety_code
53-22-36/37/39-45
유해 물질 데이터
7496-02-8(Hazardous Substances Data)
중점관리물질 필터링
별표2-141
Metabolism/Metabolites · 6건

... Both the in vitro metabolism of (3H)6-Nitrochrysene (NC) by 9000 g supernatants (S9) prepared from the livers of preweanling mice and the in vivo metabolism of (3H)NC in these animals. The in vitro covalent binding of primary metabolites of NC to DNA after further reductive and/or oxidative metabolism was then examined in an attempt to define the metabolic activation pathway responsible for the formation of carcinogen--DNA adducts in NC-treated preweanling mice. NC-1,2-dihydrodiol, NC-9,10-dihydrodiol, 6-aminochrysene (AC), and several unidentified compounds were found in ethyl acetate extracts of incubations containing (3H)NC and liver S9 from 1- or 8-day-old BLU:Ha mice. Comparison of the in vivo metabolism of NC in 1-day-old animals and 8-day-old animals which had been treated with NC on day 1 indicated that the formation of AC and the two NC dihydrodiols was greater in the younger animals. Further metabolism of NC-1,2-dihydrodiol by S9 from 8-day-old mice yielded AC-1,2-dihydrodiol as a major product. Incubation of AC-1,2-dihydrodiol, calf thymus DNA and liver microsomes from 3-methylcholanthrene-induced rats yielded a single major adduct that was chromatographically and chemically identical to the major adduct formed in (3H)NC- and (3H)-AC-treated preweanling mice. The results indicated that the major DNA adduct found in vivo is derived from the further metabolism of the proximate carcinogen AC-1,2-dihydrodiol.

... The major metabolic activation pathway of 6-nitrochrysene in newborn mice is initially through the formation of the proximate tumorigen trans-1,2-dihydro-1,2-dihydroxy-6-aminochrysene with subsequent formation of 1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-aminochrysene ... The ability of human hepatic and pulmonary microsomes to metabolize 6-nitrochrysene was investigated. The major metabolites identified in 11 hepatic microsomes were trans-1,2-dihydro-1,2-dihydroxy-6-nitrochrysene, trans-9,10-dihydro-9,10-dihydroxy-6-nitrochrysene, trans-1,2-dihydro-1,2-dihydroxy-6-aminochrysene, 6-aminochrysene, and chrysene-5,6-quinone. Following the incubations of 6-nitrochrysene with 11 different human pulmonary microsomes, qualitatively similar metabolic patterns were obtained, although quantitative differences were evident. These results demonstrated that human liver and lung are capable of metabolizing 6-nitrochrysene to known potent carcinogenic metabolites via ring oxidation and nitroreduction. In an attempt to define the roles of individual human hepatic P450 involved in the metabolism of 6-nitrochrysene, the catalytic activities known to be associated with a specific P450 were analyzed and compared with the levels of each metabolite of 6-nitrochrysene formed with the same microsomes. Rates of phenacetin O-deethylation (P450 1A2) and nifedipine oxidation (P450 3A4) were well correlated with the rates of formation of trans-1,2-dihydro-1,2-dihydroxy-6-nitrochrysene and 6-aminochrysene, respectively. Inhibition studies with specific P450 inhibitors and antibodies further support the view that P450 1A2 and P450 3A4 are the major forms responsible for the formation of trans-1,2-dihydro-1,2-dihydroxy-6-nitrochrysene and 6-aminochrysene, respectively, in human liver. Further metabolism of trans-1,2-dihydro-1,2-dihydroxy-6-nitrochrysene appears to require P450 3A4. In the human lung, P450 1A1 appears to play a major role in the metabolism of 6-nitrochrysene to trans-1,2-dihydro-1,2-dihydroxy-6-nitrochrysene ...

... Three female CD rats were injected ip with [3,4,9,10-3H]6-nitrochrysene (6-NC) [9 umol/rat (346 uCi/rat)], and urine and feces were collected daily for 3 days. In the first 24 hr, radioactivity corresponding to 1.3% of the dose was excreted in the urine, whereas 23.0% was recovered in the feces. After 3 days, the total excretions in urine and feces were 2.8% and 34.9% of the dose, respectively. Radioactivity measured in various organs 3 days after injection of [3,4,9,10-3H]6-NC amounted to 24.8% of the administered dose. Fecal metabolites were identified, based on comparison of their chromatographic characteristics with those of standards, as trans-1,2-dihydro-1,2-dihydroxy-6-NC, chrysene-5,6-quinone, and 6-aminochrysene (6-AC); the structure of the latter was further confirmed by mass spectrometry and UV spectral analysis. Metabolites identified in the urine were 6-AC, trans-1,2-dihydro-1,2-dihydroxy-6-NC, and trans-9,10-dihydro-9,10-dihydroxy-6-NC in free forms and also as glucuronide and/or sulfate conjugates. The (32)P-postlabeling assay was used to determine the metabolic pathways that were leading to DNA adduct formation in the target (colon) and nontarget (liver, lung, and mammary tissues) organs of female CD rats injected with 6-NC under conditions identical to those of the bioassay (total, 14.8 umol/rat; single ip injections on days 1, 8, 15, 22 and 29). Twenty-four hr after the last carcinogen administration, the levels of the adduct derived from trans-1,2-dihydro-1,2-dihydroxy-6-AC were higher than those derived from N-hydroxy-6-AC in all organs examined; however, the highest levels of DNA adducts were found in the lung and not in the target organ, the colon. Although the role of each adduct in colon carcinogenesis needs to be determined, the results favor the ring oxidation and nitroreduction combination pathway as the primary contributor to the activation of 6-NC as a colon carcinogen in the rat.

The environmental pollutant 6-nitrochrysene (6-NC) is a potent mammary carcinogen in the rat. To determine if the results obtained in 6-NC-treated rodents can be applicable to humans, ... its metabolic activation in primary cultures of human breast cells prepared from tissues obtained from reduction mammoplasty from 3 women and in a cultured, immortalized human mammary epithelial cell line (MCF-10A), as well as estrogen-dependent (MCF-7) and estrogen-independent (MDA-MB-435s) human breast cancer cell lines /was examined/. Metabolites identified following 24 hr incubations of (3H)6-NC (2.5, 5.0 and 10 uM) with human breast cells were derived from ring-oxidation (trans-1,2-dihydroxy-1,2-dihydro-6-nitrochrysene [1,2-DHD-6-NC]) and nitro-reduction (6-aminochrysene [6-AC]); chrysene-5,6-quinone (C-5,6-Q) was also detected. Levels of metabolites (pmol/mg protein) varied greatly depending on the concentration of 6-NC and the individual breast tissue used; 1,2-DHD-6-NC, ranged from not detected to 15.6 +/- 1.0; 6-AC, from 11.5 +/- 4.0 to 155 +/- 10.2; C-5,6-Q, from 18.3 +/- 10.8 to 196.7 +/- 15.4. Qualitatively similar metabolic profiles were obtained upon incubation of [(3)H]6-NC with MCF-10A, MCF-7 and MDA-MB-435s. ... 1,2-dihydroxy-6-aminochrysene (1,2-DH-6-AC ranged from not detected to 50.4 +/- 9.8). Some of the metabolites identified in our study are known to be proximate carcinogenic forms of 6-NC in rodents. MCF-7 was the most efficient cell line in catalyzing 6-NC to genotoxic metabolites, and ... the major DNA adduct is chromatographically identical to that found in the mammary gland of rats treated by gavage with 6-NC and that obtained from the incubation of [(3)H]1,2-DHD-6-NC with MCF7 cells or from nitro-reduction of 1,2-DHD-6-NC in the presence of 2'-deoxyguanosine 5'-monophosphate in vitro. This is the first report to demonstrate the ability of human breast cells, MCF-10A, and breast cancer cell lines to activate 6-NC to metabolites that can damage DNA.

For more Metabolism/Metabolites (Complete) data for 6-Nitrochrysene (8 total), please visit the HSDB record page.

6-nitrochrysene has known human metabolites that include N-hydroxy-6-AC and 1,2-DHD-6-NC.

Absorption, Distribution and ExcretionIn rats injected with [3,4,9,10-3H]6-nitrochrysene i.p., after 24 hr, only 1.3% of the dose was excreted in the urine and 23% in the feces.

용도 및 제조

Uses · 2건

Used as the internal standard in the analysis of nitroarenes; [HSDB] Produced directly or indirectly from incomplete combustion; NitroPAHs are formed from PAHs through nitration during combustion (i.e. diesel exhaust) or in the atmosphere; [INCHEM EHC]

Internal standard in the chemical analysis of nitroarenes. It is available for research purposes at greater than or equal to 98% purity and is also available at a certified purity of 98.9% as a reference material.

Methods of Manufacturing... Heating chrysene with aqueous nitric acid in acetic acid ... also ... by briefly heating chrysene with nitric acid and concentrated sulfuric acid in acetic acid at 40 °C
응용 분야 · 2건

용도There is no evidence that 6-nitrochrysene has been used commercially for any purpose. 6-Nitrochrysene is used as an internal standard in the chemical analysis of nitroarenes (IARC 1989). It is available for research purposes at a purity of at least 98% and as a reference material at a certified purity of 98.9%.

일반 설명Chrome-red thick prismatic crystals or orange-yellow needles (recrystallized from pyridine or xylene).

공급사14 곳

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