スダン I

1-(Phenylazo)-2-naphthol

HCID 13297

基本情報

CAS
40339-35-3
標準SMILES
Oc1ccc2ccccc2c1N=Nc1ccccc1
InChIKey
MRQIXHXHHPWVIL-UHFFFAOYSA-N
分子式
C16H12N2O
平均分子量
248.28 g/mol
単同位体質量
248.094963

概要

C.I. Solvent Yellow 14 can cause cancer according to The National Toxicology Program.

名称と識別子

優先名称
1-(Phenylazo)-2-naphthol
IUPAC
1-phenyldiazenylnaphthalen-2-ol
現地名
スダン I
英語名
Sudan I
分子式
C16H12N2O
分子量
248.28

名称と別名

842-07-9C.I. Solvent Yellow 141-(Phenylazo)-2-naphthalenolSudan Orange RAGrasal OrangeCalcogas MOrange PelCeres Orange RSoudan ISudan Orange RPyronalorangeCarminaph
名称をさらに表示
スダン IオイルオレンジEソルベントイエロー14C.I.ソルベントイエロー141-フェニルアゾ-2-ナフトール2-ヒドロキシ-1-(フェニルアゾ)ナフタレン1-(フェニルアゾ)-2-ヒドロキシナフタレン1-(フェニルアゾ)-2-ナフトールスダンイエロー1-(フェニルアゾ)-2-ナフタレノールスダンIオイルオレンジスーダンオレンジRスーダンオレンジRAスカーレットB1-(フェニルアゾ)ナフタレン-2-オールスーダンイエローズダンIスカーレット B(スダンI)スダンエローSUDANSOLVENT YELLOW 14SUDAN YELLOWSolvent Yellow RSOLVENT YELLOW 15Oil-soluble yellow1-PHENYLAZO-2-NAPHTHOLSudan I, 1-Phenylazo-2-naphthol1-(Phenyldiazenyl)naphthalen-2-olSudan J
DunkelgelbFat Orange IFat Orange RSFettorange lgCerotinorange GOrganol OrangeStearix OrangeCalcogas Orange NC

データベース識別子

CAS
40339-35-3、71351-99-0、842-07-9
PubChem CID
13297
DTXSID
DTXSID4021135
ChEMBL
CHEMBL1397023
ChEBI
CHEBI:30958
UNII
48I7IBB68J
EC Number
212-668-2
Nikkaji
J190.838C、J3.321.022A、J3.336G、J3.602.610C

物性

構造計算による物性

XLogP
4.1
極性表面積
45 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
2
重原子数
19

実験および物理化学的性質

Chemical ClassesDyes -> Azo Dyes
CosmeticsCosmetics ingredient -> Colorant
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.86
Density0.18 (NTP, 1992) - Less dense than water; will float
Color/FormBRICK-RED CRYSTALS (LEAFLETS FROM ETHANOL)

物理化学的性質

融点
131 · 131-133 °C
沸点
391.35 °C · 391.35°C (rough estimate)
比重(密度)
1.1077 · 1.1077 (rough estimate)
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
1.58 · 1.5800 (estimate)
貯蔵温度
Sealed in dry,Room Temperature

化学的性質

化学的特性orange-red powder

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: 2-Naphthalenol, 1-(phenylazo)-

Hazard Traits - Carcinogenicity

Regulation (EC) No 178/2002 (amended)

REACH registered substance: 1-phenylazo-2-naphthol (EC: 212-668-2)

C.I. Solvent yellow 14: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Azo Dyes that Cleave to Aromatic Amines of Potential Toxicological Concern: Human health tier II assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Exposure to this compound may result in irritation.
Hazards SummaryMay cause skin sensitization; [eChemPortal: ESIS] May cause irritation; Possible sensitizer; [MSDSonline]
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 件

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 件

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 adsorbent 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.

Personal Protective Equipment (PPE) · 1 件

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)

毒性情報

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Ongoing Test Status · 1 件

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=842-07-9]

Human Toxicity Excerpts · 3 件

SKIN SENSITIVITY OF RED 225 & ITS IMPURITIES DETERMINED BY PATCH TEST. COMMERCIAL PREPN SHOWED POSITIVE REACTIONS IN ALL 6 SUBJECTS. SUDAN I ISOLATED & IDENTIFIED. SUDAN I ALSO SHOWED POSITIVE REACTIONS IN ALL 6 SUBJECTS.

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/

"Kumkums" are colored cosmetics frequently applied to the center of the forehead by Hindu women. Pigmented allergic contact dermatitis to "kumkum" was reported recently. It was associated with Brilliant Lake Red R and Sudan I allergy. These might be the causitive allergens. Three of 7 brands of red "kumkums" analyzed by gas chromatography-mass spectrophotometry were found to contain various concentrations of Sudan I. They ranged from 2.789 mg/g to 8.694 mg/g. Sudan I is probably the cause of pigmented allergic contact dermatitis in red "kumkum".

Carcinogen Classification · 6 件

Sudan I

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 8: (1975) Some Aromatic Azo Compounds

1987

1987

C.I. Solvent Yellow 14

Non-Human Toxicity Excerpts · 5 件

PARAFFIN WAX PELLETS CONTAINING 12.5% ... IMPLANTED INTO URINARY BLADDERS OF FEMALE (C57XIF)F1 MICE; 14/100 SURVIVING 25 OR MORE WK DEVELOPED CARCINOMAS OF BLADDER, & 2 ... SHOWED SQUAMOUS METAPLASIA OF BLADDER. ... BLADDER CARCINOMA IN CONTROLS ... WAS 4/89 ... .

GROUPS OF 47 CBA & 35 STOCK MICE ... 10 WK OLD, RECEIVED DIET ... @ CONCN OF 1000 MG/KG OF DIET FOR 12 MO (TOTAL DOSE, 1400 MG/ANIMAL). ... INCIDENCE OF HEPATOMAS AFTER 120 WK ... WAS LOWER IN TREATED THAN IN UNTREATED ... GROUP OF 20 RATS ... FED ... @ CONCN OF 1000 MG/KG OF DIET FOR LIFESPAN. ... NO TUMORS WERE FOUND.

... 18 MALE & 18 FEMALE STOCK MICE, 2-3 MO OF AGE ... GIVEN 17-20 SC INJECTIONS OF 0.25 ML OF 3% SOLN ... IN ARACHIS OIL @ 3-WK INTERVALS. BETWEEN 305TH & 615TH DAY ... 8/12 MALES HAD DEVELOPED ... 6 HEPATOMAS, 1 ADENOCARCINOMA OF LUNG & 1 SQUAMOUS CARCINOMA @ INJECTION SITE. ... 3 FEMALES DEVELOPED /SIMILAR/ TUMORS ... .

PARAFFIN WAX PELLETS WEIGHING 10-18 MG & CONTAINING 12% SUDAN I WERE IMPLANTED INTO URINARY BLADDERS OF 32 ALBINO MICE FOR 40 WK. 8 ... DEVELOPED CARCINOMAS OF BLADDER, 6 ... HAD BENIGN TUMORS & 5 SHOWED SQUAMOUS METAPLASIA OF BLADDER. IN 56 CONTROLS ... 2 CARCINOMAS, 9 SQUAMOUS METAPLASIA & 3 BENIGN TUMORS ... .

For more Non-Human Toxicity Excerpts (Complete) data for C.I. SOLVENT YELLOW 14 (9 total), please visit the HSDB record page.

Evidence for CarcinogenicityNo data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

安全データ

wgk
2
tsca
TSCA listed
rtecs
QL4900000
毒性
mmo-sat 300 ng/plate SCIEAS 236,933,87
hs_code
32129000
risk_code
68-53-43-40-36/37/38

化学と産業

薬理情報

Mechanism of Action · 1 件

Sudan I activated by pre-incubation with microsomal enzymes of rat livers covalently binds to DNA from calf thymus. Benzenediazonium ion formed from Sudan I by activation with microsomal enzymes is the principal active metabolite, which binds to DNA. Enzymatic hydrolysis of modified 14(C)-labelled DNA, followed by separation of deoxynucleosides on a Sephadex G-10 column revealed that deoxyguanosine is the principal target for the binding of activated Sudan I.

Metabolism/Metabolites · 6 件

ADMIN ORALLY TO RABBITS, THIS DYESTUFF ... UNDERGOES REDUCTIVE SCISSION, BUT IS ALSO METABOLIZED BY HYDROXYLATION OF BENZENE RING.

YIELDS 2,6-DIHYDROXY-1-PHENYLAZONAPHTHALENE, 2-HYDROXY -1-(PARA-HYDROXYPHENYLAZO)NAPHTHALENE, & 1-PHENYLHYDRAZO-2-NAPHTHOL IN RABBITS & RATS. /FROM TABLE/

... ORAL ADMIN IN RABBITS, 1.2% ... UNCHANGED, 1.5% AS 1-PARA-HYDROXYPHENYLAZO-2-NAPHTHOL, 44% AS FREE & CONJUGATED PARA-AMINOPHENOL, 24% AS PARA-AMINOPHENYLGLUCURONIDE, 0.5% AS ORTHO-AMINOPHENOL & 1.1% AS ANILINE; PARA-ACETAMIDOPHENYL GLUCURONIDE, 1-PARA-HYDROXYPHENYLAZO-2-NAPHTHOL GLUCURONIDE & 1-AMINO-2-NAPHTHOL ... .

... GLUCURONIDES OF 4',6-DIHYDROXY-1-PHENYLAZO-2-NAPHTHOL & 4'- & 6-HYDROXY-1-PHENYLAZO-2-NAPHTHOL WERE PRESENT IN ... BILE & URINE OF RABBITS. URINE ALSO CONTAINED 1-AMINO-2-NAPHTHYL HYDROGEN SULFATE, 1-AMINO-2-NAPHTHYL GLUCURONIDE & N-GLUCURONIDES OF 1-PHENYLHYDRAZO-2-NAPHTHOL & OF 4'-HYDROXY-1-PHENYLHYDRAZO-2-NAPHTHOL ... .

For more Metabolism/Metabolites (Complete) data for C.I. SOLVENT YELLOW 14 (6 total), please visit the HSDB record page.

Sudan I has known human metabolites that include 1-Amino-2-naphthol and aniline.

用途と製造

Uses · 3 件

Used as a dye for hydrocarbon solvents, oils, fats, waxes, shoe and floor polishes, gasoline, soap, colored smokes, cellulose ether varnishes, and styrene resins; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

DYE FOR HYDROCARBON SOLVENTS, OILS, FATS, WAXES, SHOE & FLOOR POLISHES, GASOLINE, SOAP, COLORED SMOKES, CELLULOSE ETHER VARNISHES, & STYRENE RESINS

U.S. Imports · 2 件

(1977) 8.25X10+5 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 1.14X10+7 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 2 件

(1977) PROBABLY GREATER THAN 1.59X10+7 GRAMS

(1979) 1.59X10+8 GRAMS

Consumption PatternsESSENTIALLY 100% AS A DYE
Methods of ManufacturingCOUPLING OF DIAZOTIZED ANILINE WITH 2-NAPHTHOL
Household Products · 2 件

Cosmetics product ingredient: CI Solvent Yellow 14

Information on 3 consumer products that contain C.I. Solvent Yellow 14; 1-phenylazo-2-naphthol in the following categories is provided:

応用分野 · 3 件

用途ガソリン、インキ、油脂製品、合成樹脂の着色。

用途ズダンI定量用HPLC標準品。

一般的な説明Dark reddish-yellow leaflets or orange powder. Slight odor.

調製方法

製造方法Aniline diazo, and Naphthalen-2-olcoupling.

純化方法Crystallise the dye from EtOH. It forms Cu and Ni salts. [Beilstein 16 H 162, 16 I 254, 16 II 70, 16 III 129, 16 IV 228.]

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