Dibenzo[b,def]chrysen-7,14-dion

Dibenzo(b,def)chrysene-7,14-dione

HCID 31412CAS 128-66-5

Grundinformationen

Standard-SMILES
O=C1c2ccccc2-c2ccc3c4c(ccc1c24)-c1ccccc1C3=O
InChIKey
ZTWQZJLUUZHJGS-UHFFFAOYSA-N
Summenformel
C24H12O2
Durchschnittliche Molmasse
332,3 g/mol
Monoisotopische Masse
332,08372962

Überblick

C.i. vat yellow 4 is a viscous orange liquid. Used for coloring of cotton, wool and cellulose acetate.

Namen und Bezeichner

Bevorzugter Name
Dibenzo(b,def)chrysene-7,14-dione
IUPAC
hexacyclo[10.10.2.02,7.09,23.013,18.020,24]tetracosa-1(23),2,4,6,9,11,13,15,17,20(24),21-undecaene-8,19-dione
Lokaler Name
Dibenzo[b,def]chrysen-7,14-dion
Englischer Name
Vat Yellow 4
Summenformel
C24H12O2
Molmasse
332.35

Namen und Synonyme

Vat yellow 4C.I. Vat Yellow 4128-66-5YellowTyrion YellowTyrian Yellow I-GOKVat Yellow ZhKhYellow GK baseHelanthrene YellowVat Golden YellowDibenzo[B,def]chrysene-7,14-dioneTinon Golden Yellow GK
Weitere Namen anzeigen
NSC30987C.I.59100NSC 30987NSC-30987C.I.VATYELLOW4Anthravat golden yellowAmanthrene golden yellowVat yellow 4 (C.I. 59100)Arlanthrene golden yellow
Golden Yellow ZhKhTinon Golden YellowC.I. Vat YellowMayvat Golden YellowCaledon Golden YellowCibanone Golden YellowHostavat Golden YellowLeucosol Golden Yellow

Datenbank-Bezeichner

CAS
128-66-5
PubChem CID
31412
DTXSID
DTXSID6021454
ChEBI
CHEBI:82548
UNII
8XO6A4G496
EC Number
204-903-2
Nikkaji
J5.411I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,4
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

Chemical ClassesDyes -> Anthraquinone Dyes
SpringerMaterials PropertiesDiamagnetic susceptibility
Solubilitygreater than or equal to 100 mg/mL at 75 °F (NTP, 1992)
Flash Point · 2 Einträge

greater than 200 °F (NTP, 1992)

Flash Point > 93 °C

Physical Description · 2 Einträge

C.i. vat yellow 4 is a viscous orange liquid. Used for coloring of cotton, wool and cellulose acetate.

Orange liquid; [CAMEO]

Physikochemische Eigenschaften

Schmelzpunkt
385 °C · 385 °C
Siedepunkt
429.48 °C · 429.48°C (rough estimate)
Dichte
1.1459 · 1.1459 (rough estimate)
Brechungsindex
1.4891 · 1.4891 (estimate)
Stabilität
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS Datenbank
128 · 128-66-5

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS ClassificationNot Classified

Gefahrenhinweise

Regulatory InformationChemical: Dibenzo[b,def]chrysene-7,14-dione
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and irritating fumes. (NTP, 1992)
Hazards SummaryAnthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and coma; Deaths have been reported after children ingested Rhamnus berries; [HSDB]
Reactive GroupHydrocarbons, Aromatic
Special Reports · 2 Einträge

REVIEW OF INHALATION (TOTAL-BODY-EXPOSURE) STUDIES OF COLORED CHEM SMOKES. ACUTE TOXICITIES, TIME TO DEATHS, & GROSS SIGNS COMPARED. TOXICOLOGICAL EVALUATION OF DYES IN SMOKE MIXT INCL. ONE OF THE DYES USED IN CHEM SMOKES IS DIBENZO(B,DEF)CHRYSENE-7,14-DIONE.[OWENS EJ, WARD DM; USNTIS AD/A REP ISS NO 003827/3GA 72 PP (1974)]

DHEW/NCI; Bioassay of C.I. Vat Yellow 4 for Possible Carcinogenicity (1979) Technical Rpt Series No. 134 DHEW Pub No. (NIH) 79-1389

Sicherheit und Schutzausrüstung

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

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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.

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=128-66-5]

Human Toxicity Excerpts · 1 Eintrag

Most organic azo dyes are potential skin sensitizers, the most important of which are paraphenylenediamine and its analogs. Water soluble azo dyes are more likely to cause clinical sensitization than insoluble dyes. ... In addition to allergic eczematous contact dermatitis, color developing solutions have caused lichen planus like eruptions. /Organic dyes/

Carcinogen Classification · 6 Einträge

Vat Yellow 4

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 48: (1990) Some Flame Retardants and Textile Chemicals, and Exposures in the Textile Manufacturing Industry

1990

1989

C.I. Vat yellow 4

Non-Human Toxicity Excerpts · 2 Einträge

Vat yellow 4 (C.I. 59100) was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. Vat yellow 4 was tested over a wide range of doses (0, 100, 333, 1000, 3333, and 10,000 ug/plate) in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. Vat yellow 4 was negative in these tests and the highest ineffective dose level tested in any Salmonella tester strain was 10,000 ug/plate.

Despite their widespread use and potential for significant human exposure, genotoxicity data on anthraquinones and other dyes are limited. In this study, 16 anthraquinones and one azo dye (Solvent Red 1) were selected for testing using the thymidine locus and micronucleus (MN) analysis in L5178Y/TK(+ or -)-3.7.2C mouse lymphoma cells. Six of the dyes were from the same lot used in the NTP rodent bioassay. The dyes used were all production lots and thus varied in their purity. Disperse Blue 7, 2-aminoanthraquinone; 1-amino-2-methylanthraquinone, Disperse Blue 3 and Disperse Red 11 were genotoxic (inducing 1814 mutants/10(6) survivors, 369 MN/1000 cells at 13% survival; 397 mutants/10(6) survivors, 196 MN/1000 cells at 21% survival; 178 mutants/10(6) survivors, 119 MN/1000 cells at 51% survival; 264 mutants/10(6) survivors, 109 MN/1000 cells at 15% survival, respectively). Reactive Blue 19 was weakly mutagenic (inducing 144 mutants/10(6) survivors, but only 8 MN/1000 cells at 13% survival). Vat Yellow 4 and Solvent Red 1, with exogenous activation, were also mutagenic (inducing 300 mutants/10(6) survivors, 18 MN/1000 cells at 57% survival, and 100 mutants/10(6) survivors and 16 MN/1000 cells at 22% survival, respectively). With activation 1-nitro-2-methylanthraquinone was judged to give an equivocal mutagenicity response. The maximum test concentration was limited for some compounds by their solubility. Those chemicals that did not induce mutation or cytotoxicity at the limits of solubility were classified separately. Compounds which were not evaluated without exogenous activation because of insolubility but were evaluated with activation include 1-nitro-2-methylanthraquinone, Solvent Red 1 and Vat Yellow 4.

Evidence for Carcinogenicity · 1 Eintrag

Evaluation: There is limited evidence for the carcinogenicity of Vat Yellow 4 in experimental animals. No data were available from studies in humans on the carcinogenicity of Vat Yellow 4. Overall evaluation: Vat Yellow 4 is not classifiable as to its carcinogenicity to humans (Group 3).

Sicherheitsdaten

tsca
TSCA listed
Giftige Stoffe Daten
128-66-5(Hazardous Substances Data)

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

Used as a dye for cotton, silk, wool, and paper; [HSDB]

Pulp and Paper Processing [Category: Industry]

DYE FOR COTTON, SILK, WOOL & PAPER, FOR PRINTING COTTON

U.S. Imports · 2 Einträge

(1977) 3.88X10+6 G (PRINCPL CUSTMS DISTS)

(1979) 3.50X10+6 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 Einträge

(1978) PROBABLY GREATER THAN 2.27X10+6 G

(1979) PROBABLY GREATER THAN 2.27X10+6 G

Consumption PatternsESSENTIALLY 100% AS A DYE
Methods of ManufacturingREACTION OF 3-BENZOYLBENZANTHRONE WITH ALUMINUM CHLORIDE & AN OXIDIZING AGENT; REACTION OF 1,5-DIBENZOYLNAPHTHALENE WITH SODIUM AND ALUMINUM CHLORIDES
General Manufacturing InformationDibenzo[b,def]chrysene-7,14-dione: ACTIVE

Anwendungen

VerwendenVat Yellow 4 is a commercial dye used in textiles. Polyaromatic hydrocarbon with potential carcinogenic activity.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.

Darstellung

synthetische(a) 3-Benzoylbenzanthroneand Aluminium chloride and antioxidant for the closed-loop response; (b) 1,5-Dibenzoyl-2-naphthaenein Aluminium chloride and sodium chloride were under existing closed-loop response.

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