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パーマネントオレンジ

Fast Orange

HCID 18981
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
3468-63-1
標準SMILES
O=[N+]([O-])c1ccc(N=Nc2c(O)ccc3ccccc23)c([N+](=O)[O-])c1
InChIKey
HBHZKFOUIUMKHV-UHFFFAOYSA-N
分子式
C16H10N4O5
平均分子量
338.27 g/mol
単同位体質量
338.06511943

概要

D&C Orange No. 17 can cause cancer according to The Food and Drug Administration (FDA).

名称と識別子

優先名称
Fast Orange
IUPAC
1-[(2,4-dinitrophenyl)diazenyl]naphthalen-2-ol
現地名
パーマネントオレンジ
英語名
Pigment Orange 5
分子式
C16H10N4O5
分子量
338.27

名称と別名

3468-63-1Permatone OrangeHansa Orange RNLight Orange RSilopol Orange RCarnelio Red 2GChromatex Orange RGraphtol Red 2GLVersal Orange RNLLake Red 2GLIsol Fast Red 2GCalcotone Orange 2R
名称をさらに表示
パーマネントオレンジ1-[(2,4-ジニトロフェニル)アゾ]-2-ナフタレノールピグメントオレンジ5DandCオレンジ171-[(2,4-ジニトロフェニル)アゾ]ナフタレン-2-オール1-(2,4-ジニトロフェニルアゾ)-2-ナフトールパーマネントオレンジトナーだいだい色203号ブリリアントタンゲリン13030ジニトロアニリンオレンジジニトロアニリンレッドC.I.ピグメントオレンジ5ピグメント オレンジ-5橙2031-[2-(2,4-ジニトロフェニル)ジアゼン-1-イル]ナフタレン-2-オールピグメントオレンジ5標準品橙色203号DAIDAI203c.i. 12075lakered2glD&CORANGE1711048orangefastonared2glightorangerorangeno.203carneliored2g

物性

構造計算による物性

XLogP
4.3
極性表面積
137 Ų
水素結合供与体数
1
水素結合受容体数
7
回転可能結合数
2
重原子数
25
形式電荷
0
複雑度
532

実験および物理化学的性質

CosmeticsCosmetics ingredient -> Colorant
Density1.52 No temp
Color/Form · 3 件

Reddish shade of orange

Strong bright orange

Orange powder ... paste

DecompositionWhen heated to decomposition it emits toxic fumes of NOx.
Melting Point · 2 件

302 °C

302 °C

Physical DescriptionDry Powder; Liquid; Dry Powder; CBI

物理化学的性質

融点
306 °C · 306°C(lit.)
沸点
474.44 °C · 474.44°C (rough estimate)
比重(密度)
1.3138 · 1.3138 (rough estimate)
屈折率
1.63 · 1.6300 (estimate)
貯蔵温度
-20 °C · Amber Vial, -20°C Freezer
溶解性
クロロホルム(微量)、テトラヒドロフラン(微量、加熱)
外見
個体
酸解離定数(Pka)
13.45 · 13.45±0.50(Predicted)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 42.4% (369 of 871) of reports.

Warning

H319 (51.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 871 reports by companies from 9 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 5 件

Chemical: 2-Naphthalenol, 1-[(2,4-dinitrophenyl)azo]-

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence

2-Naphthalenol, 1-[2-(2,4-dinitrophenyl)diazenyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenol, 1-[2-(2,4-dinitrophenyl)diazenyl]- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 1-[(2,4-dinitrophenyl)azo]-2-naphthol (EC: 222-429-4)

2-Naphthalenol, 1-(2,4-dinitrophenyl)azo-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Miscellaneous azodyes: Human health tier II assessment
Hazard Classes and CategoriesEye Irrit. 2 (51.7%)

安全と保護具

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

化学と産業

用途と製造

Uses · 3 件

... finds principle application in air-drying systems, including a variety of printing inks

Pigment in paints

Used on a moderately large scale in the printing ink industry

U.S. Production · 3 件

2023: 100,000 - <250,000 lb

2-Naphthalenol, 1-[(2,4-dinitrophenyl)azo]- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Available from the Database Query page at: http://www.epa.gov/hpv/pubs/general/opptsrch.htm on 2-Naphthalenol, 1-

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7384]

Consumer UsesPigment
Industry UsesPigment
Household ProductsCosmetics product ingredient: D&C Orange No. 17
General Manufacturing Information · 3 件

Construction

2-Naphthalenol, 1-[2-(2,4-dinitrophenyl)diazenyl]-: ACTIVE

... relatively low hiding power and good lightfastness in full shades, but poor tint lightfastnesds. It shows poor bleed but acceptable base resistance

応用分野

一般的な説明Pigment orange 5 is an azo pigment, which can be produced industrially by a diazotization and coupling sequence in which diazotized dinitroaniline is coupled into β-naphthol.

上流・下流製品情報

上流原料

発煙硫酸

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
hansaorangern
Syton Fast Red 2GHelio Fast Orange RNLutetia Fast Orange RBrilliant tangerine 13030Irgalite Fast Red 2GLNippon Orange X-881Segnale Light Orange RNGDainichi Permanent Red GG

データベース識別子

CAS
3468-63-1
PubChem CID
18981
DTXSID
DTXSID6029258
ChEMBL
CHEMBL1982121
UNII
E27LT0986O
EC Number
222-429-4
Nikkaji
J34.111H、J958.162F
色
オレンジからダークレッド
BRN
964718 · 964718
Henry's Law Constant
1.1 · 1.1×109 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
洗浄剤化粧品食品および飲料パーソナルケア
化粧品成分の機能
着色剤
InChI
1S/C16H10N4O5/c21-15-8-5-10-3-1-2-4-12(10)16(15)18-17-13-7-6-11(19(22)23)9-14(13)20(24)25/h1-9,21H/b18-17+
InChIKey
HBHZKFOUIUMKHV-ISLYRVAYSA-N
SMILES
Oc1ccc2ccccc2c1\N=N\c3ccc(cc3[N+]([O-])=O)[N+]([O-])=O
LogP
3.61 · 3.610 (est)
CAS データベース
3468 · 3468-63-1(CAS DataBase Reference)
EPAの化学物質情報
5 · C.I. Pigment Orange 5 (3468-63-1)
Protective Action Criteria (PAC) · 3 件

30 [mg/m3]

330 [mg/m3]

2000 [mg/m3]

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Orange 5 is expected to be immobile in soil(SRC). Volatilization of C.I. Pigment Orange 5 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.1X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(3). C.I. Pigment Orange 5 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.3X10-12 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Orange 5 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 9.1X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 10(SRC), from an estimated log Kow of 5.7(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), C.I. Pigment Orange 5, which has an estimated vapor pressure of 9.3X10-12 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 C.I. Pigment Orange 5 may be removed from the air by wet or dry deposition(SRC). C.I. Pigment Orangee 5 contains functional groups that are typically chromophores which absorb at wavelengths >290 nm(3); therefore C.I. Pigment Orange 5 may be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of C.I. Pigment Orange 5 can be estimated to be 1.3X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that C.I. Pigment Orange 5 is expected to be immobile in soil.

Human Toxicity Excerpts · 1 件

/HUMAN EXPOSURE STUDIES/ Eight patients suffering from pigmented contact dermatitis caused by the commercial Brilliant Lake Red R were patch tested with purified Sudan I and its several chemical analogs. Positive reactions were observed to Sudan I, Orange SS, Brilliant Lake Red R, Vacanceine Red, Yellow OB and Sudan II. Negative patch tests were obtained with Toluidine Red, Permanent Orange /Pigment Orange 5/, Lithol Red and Sudan III. The commercial Brilliant Lake Red R, which is said to be the most important causative agent of pigmented contact dermatitis, contained Sudan I as a major impurity. The patients reacting to Brilliant Lake Red R always gave a positive reaction to Sudan I, but those reacting to Sudan I did not always give a positive reaction to Brilliant Lake Red R. ...

Artificial Pollution SourcesC.I. Pigment Orange 5's production and use in paints(1) and printing inks(2) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF of 10 was calculated for C.I. Pigment Orange 5(SRC), using an estimated log Kow of 5.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for C.I. Pigment Orange 5 is estimated as 9.1X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that C.I. Pigment Orange 5 is expected to be essentially nonvolatile from water surfaces(2). The Henry's Law constant of C.I. Pigment Orange 5 indicates that volatilization from moist soil surfaces is not expected(SRC). C.I. Pigment Orange 5 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.3X10-12 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 件

/GENOTOXICITY/ The induction of DNA damage by commonly used printing ink pigment, CI pigment orange 5 (CI 12075) ... was investigated in freshly isolated rat hepatocytes with the comet assay. ... The /pigment is/ virtually insoluble in aqueous solutions, and /has/ not been tested extensively for toxicological effects. CI pigment orange 5 increased the levels of DNA damage at 5 ug/mL (P < 0.02) ... . (P < 0.002). The effect of incubation time (20, 40, and 80 min) of the same concentrations of the pigment was tested. The levels of DNA damage were increased up to 80 min...

/GENOTOXICITY/ This study involved 19 dyes, selected from a list of 34 colorants considered to be representative of those ... used in the trade ... . They were tested for their ability to create revertants in the Ames Salmonella typhimurium/mammalian microsome reversion test system. Two variations of the standard Ames test were also used: the colorants were mixed with the warm top agar before spreading on the minimal plates, and the colorants were added to mouse liver homogenate, generating solution, and bacteria and shaken at 37 °C for 30 min before plating. All colorants were dissolved in dimethyl sulfoxide and all were tested in the presence and absence of liver microsomes. Two colorants, para red (color index (CI) number 12070) and dinitroaniline orange (CI 12075), were weakly mutagenic. Para red requires the presence of liver homogenate to produce mutagenicity. Dinitroaniline orange is a direct mutagen. Both colorants revert only the frameshift strains that were tested (TA1538 and TA98).

/GENOTOXICITY/ ... As a sequel to an earlier study of food colorants and related compounds, the Salmonella/mammalian microsome assay was used to test a number of colorants commonly used in drugs and cosmetics. These agents were mostly lakes, which are dye-alumina complexes, or insoluble salts from which the dyes were solubilized prior to mutagenicity testing. Agents causing mutations in Salmonella typhimurium were D & C Red No. 19, D & C Red No. 36 and D & C Orange No. 17. Rat liver microsomes were used.

/GENOTOXICITY/ Dyes (37) including 3 anthraquinone, 22 azo; 5 xanthene, 5 fluorandiol and 2 thioindigo dyes were tested for mutagenic potential with the Salmonella/mammalian-microsome test. Two frame-shift histidine mutants (TA1537 and TA98) and 2 base-pair substituted histidine mutants (TA1535 and TA100) of S. typhimurium were employed. Both the spot test and the plate-incorporation assay indicated that 1 azo dye, D&C Orange No. 17, was mutagenic with 3 of the bacterial test strains. The mutagenic response of D&C Orange No. 17 was depressed by the addition of the microsomal fraction from rat livers. Of the chemicals used to synthesize D&C Orange No. 17, beta-naphthol was not mutagenic but 2,4-dinitroaniline was mutagenic to the same Salmonella strains as D&C Orange No. 17. Dimethyl sulfoxide extracts of lipsticks of similar formula but with and without D&C Orange No. 17 were tested in the plate incorporation assay. Only those containing D&C Orange No. 17 were mutagenic and the dye was mutagenic at concentrations consumed in normal (human) daily use.

Environmental Abiotic Degradation · 1 件

C.I. Pigment Orange 5 is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). C.I. Pigment Orange 5 contains functional groups which are typically chromophores and absorb at wavelengths >290 nm(1); therefore C.I. Pigment Orange 5 may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 件

Occupational exposure to C.I. Pigment Orange 5 may occur through inhalation of dust and dermal contact with this compound at workplaces where C.I. Pigment Orange 5 is produced or used. Use data indicate that the general population may be exposed to C.I. Pigment Orange 5 via dermal contact with consumer products containing this compound. (SRC)

Environmental Fate/Exposure Summary · 1 件

C.I. Pigment Orange 5's production and use in paints and printing inks may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 9.3X10-12 mm Hg at 25 °C indicatesC.I. Pigment Orange 5 will exist solely in the particulate phase in the atmosphere. Particulate-phase C.I. Pigment Orange 5 will be removed from the atmosphere by wet or dry deposition. C.I. Pigment Orange 5 contains functional groups that are typically chromophores which absorb at wavelengths >290 nm; therefore C.I. Pigment Orange 5 may be susceptible to direct photolysis by sunlight. If released to soil, C.I. Pigment Orange 5 is expected to be immobile based upon an estimated Koc of 1.3X10+5. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 9.1X10-15 atm-cu m/mole. C.I. Pigment Orange 5 is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, C.I. Pigment Orange 5 is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 10 suggests bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to C.I. Pigment Orange 5 may occur through inhalation of dust and dermal contact with this compound at workplaces where C.I. Pigment Orange 5 is produced or used. Use data indicate that the general population may be exposed to C.I. Pigment Orange 5 via dermal contact with consumer products containing this compound. (SRC)

Antidote and Emergency Treatment · 3 件

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ 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/

/SRP:/ 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/

安全データ

wgk
3
tsca
TSCA listed
rtecs
QL3854000
ridadr
1325
hs_code
32041700
risk_code
10-68-40-36
化審法
(5)-3192
消防法
危-5-II
hazard_code
Xn,Xi
safety_code
16-36/37-26
Hazard Classifications
Carc. 2Muta. 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
3468-63-1(Hazardous Substances Data)
2,4-ジニトロアニリン
亜硝酸ナトリウム
塩酸
水酸化ナトリウム
2-ナフトール
硫酸水素

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補足説明

定義本品は、平成15年厚労省令第126号に示されるだいだい色203号である。

/GENOTOXICITY/ Twenty-four lipsticks of various shades and colors were tested for mutagenicity with the histidine-requiring tester strain Salmonella typhimurium TA98. Nine lipsticks were mutagenic without microsomal (S-9) activation. Dose-response effects were observed. Eight colorants listed as ingredients of the mutagenic lipsticks were tested with and without S-9. Drug and Cosmetic (D&C) Orange No. 17, a monoazo dye with 2 nitro groups, was highly mutagenic in the absence of S-9. The mutagenic effect was decreased or lost in the presence of S-9 prepared from livers of male noninbred Sprague-Dawley rats given a single injection of Aroclor 1254. Eight lipsticks matched for ingredients other than dyes were tested. Two containing D&C Orange No. 17 were directly mutagenic. The mutagenic effect was decreased by the presence of S-9. Only D&C Orange No. 17 was sufficiently mutagenic without microsomal activation to account for the mutagenicity observed in these lipsticks. Lipsticks containing D&C Orange No. 17 and those labeled with the words may contain D&C Orange No. 17 should be suspected of being mutagenic for S. typhimurium TA98. This dye and 2,4-dinitroaniline, which may also be present, are potential health hazards (for humans).