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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 312
実験および物理化学的性質
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
SOL IN ETHANOL, ACETONE, ETHER & BENZENE; INSOL IN WATER
SOL IN PETROLEUM ETHER, CARBON DISULFIDE, CONCN HYDROCHLORIC ACID
Melting Point
268 to 271 °F (NTP, 1992)
134 °C
Physical Description
C.i. solvent yellow 14 appears as dark reddish-yellow leaflets or orange powder. Slight odor. (NTP, 1992)
Brick-red solid; [HSDB]
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
- 溶解性
- DMSO(微量)、酢酸エチル(微量)
- 外見
- 粉
- 酸解離定数(Pka)
- 13.5 · 13.50±0.40(Predicted)
- 色
- オレンジから赤または茶色
- PH
- 10.2 · 10.2 (26°C)
- 水溶解度
- 0.5 g/L · 0.5g/L(30℃)
- 安定性
- 強力な酸化剤とは相容れない。
- 主な用途
- 洗浄剤化粧品食品および飲料パーソナルケア
- InChI
- 1S/C16H12N2O/c19-15-11-10-12-6-4-5-9-14(12)16(15)18-17-13-7-2-1-3-8-13/h1-11,19H
- InChIKey
- MRQIXHXHHPWVIL-UHFFFAOYSA-N
- SMILES
- Oc1ccc2ccccc2c1N=Nc3ccccc3
- LogP
- 5.51 · 5.51
- CAS データベース
- 842 · 842-07-9(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2-Naphthalenol, 1-(phenylazo)-(842-07-9)
- EPAの化学物質情報
- 14 · C.I. Solvent Yellow 14 (842-07-9)
化学的性質
化学的特性orange-red powder
安全と法規制
GHS分類
GHS Classification
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
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
Reactivity Profile
C.I. SOLVENT YELLOW 14 is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemical is incompatible with strong oxidizing agents and strong acids (NTP, 1992).
Hazard Classes and Categories
Skin Sens. 1 (100%)
Carcinogenicity - category 2
Germ cell mutagenicity - Category 2
Carc. 2
安全と保護具
First Aid
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
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)
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
Ongoing Test Status
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
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
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
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.
National Toxicology Program Studies
A carcinogenesis bioassay of C.I. solvent Yellow 14 (94.1% pure), a widely used monoazo dye, was conducted by feeding diets containing 250 or 500 ppm of C.I. Solvent Yellow 14 to groups of 50 F344 rats of either sex for 103 weeks. Similar groups of 50 B6C3F1 mice received diets containing 500 or 1,000 ppm of C.I. Solvent Yellow 14 for 103 weeks. Groups of 50 untreated rats and mice of either sex served as controls. Throughout the bioassay, mean body weights of dosed rats and mice were slightly lower than those of controls. No compound-related clinical signs or effects on survival were observed. Increases in nonneoplastic lesions included cardiac valve fibrosis for male and female rats, lymphoid hyperplasia of the lung for male rats, and for female rats, bile duct hyperplasia, focal atrophy of the pancreatic acinus, and nephropathy. None of these effects were observed in mice. Under the conditions of this bioassay, C.I. Solvent Yellow 14 was carcinogenic in male and female F344/N rats, as evidenced by increaed incidences of neoplastic nodules of the liver. C.I. Solvent Yellow 14 was not carcinogenic for B6C3F1 mice of either sex.
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
- 化審法
- (4)-985, (5)-3042
- hazard_code
- Xn,Xi
- safety_code
- 61-46-36/37-22-36-26
- Hazard Classifications
- Aquatic Chronic 4Carc. 2Muta. 2Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 842-07-9(Hazardous Substances Data)
化学と産業
薬理情報
Mechanism of Action
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
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
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
(1977) 8.25X10+5 GRAMS (PRINCPL CUSTMS DISTS)
(1979) 1.14X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
(1977) PROBABLY GREATER THAN 1.59X10+7 GRAMS
(1979) 1.59X10+8 GRAMS
Household Products
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:
General Manufacturing Information
2-Naphthalenol, 1-(2-phenyldiazenyl)-: ACTIVE
ACCORDING TO USA INDUST SOURCES, WHEN SUDAN I IS NOT USED IN DRUGS OR COSMETICS, ITS MFR & TESTING DO NOT CONFORM TO RIGID CHEM SPECIFICATIONS, & ITS COMPOSITION MAY VARY IN ORDER TO MEET CUSTOMER SHADE & INTENSITY REQUIREMENTS.
応用分野
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー100 社
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