기본 정보
- 표준 SMILES
Oc1ccc2ccccc2c1N=Nc1ccccc1- InChIKey
MRQIXHXHHPWVIL-UHFFFAOYSA-N- 분자식
- C16H12N2O
- 평균 분자량
- 248.28 g/mol
- 단동위원소 질량
- 248.094963
개요
C.I. Solvent Yellow 14 can cause cancer according to The National Toxicology Program.
이름 및 식별자
- 우선 이름
- 1-(Phenylazo)-2-naphthol
- IUPAC
- 1-phenyldiazenylnaphthalen-2-ol
- 현지명
- 용제 황색 14
- 영어명
- Sudan I
- 분자식
- C16H12N2O
- 분자량
- 248.28
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- 4.1
- 극성 표면적
- 45 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 312
실험 및 물리화학적 성질
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]
물리화학적 성질
- 녹는점
- 131 · 131-133 °C
- 끓는 점
- 391.35 °C · 391.35°C (rough estimate)
- 밀도
- 1.1077 · 1.1077 (rough estimate)
- 증기압
- 0 Pa · 0Pa at 25℃
- 굴절률
- 1.58 · 1.5800 (estimate)
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- DMSO(약간 용해됨), 에틸아세테이트(약간 용해됨)
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 13.5 · 13.50±0.40(Predicted)
- 색상
- 주황색에서 빨간색 또는 갈색까지
- 수소이온지수(pH)
- 10.2 · 10.2 (26°C)
- 수용성
- 0.5 g/L · 0.5g/L(30℃)
- 안정성
- 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 청소용품화장품음식 및 음료개인 위생 관리
- 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
- NIST
- 2 · 2-Naphthalenol, 1-(phenylazo)-(842-07-9)
- EPA
- 14 · C.I. Solvent Yellow 14 (842-07-9)
화학적 성질
orange-red powder
안전 및 규제
GHS 분류
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)
유해성 정보
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
안전 및 보호
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)
독성 정보
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.
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- QL4900000
- 독성
- mmo-sat 300 ng/plate SCIEAS 236,933,87
- HS 번호
- 32129000
- risk_code
- 68-53-43-40-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 61-46-36/37-22-36-26
- 기존화학 물질
- KE-08651
- Hazard Classifications
- Aquatic Chronic 4Carc. 2Muta. 2Skin Sens. 1
- 스토리지 클래스
- 11 - Combustible Solids
- 유해 물질 데이터
- 842-07-9(Hazardous Substances Data)
화학 및 산업
약리 정보
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.
용도 및 제조
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.
응용 분야
일반 설명Dark reddish-yellow leaflets or orange powder. Slight odor.
제조 방법
Aniline diazo, and Naphthalen-2-olcoupling.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
관련 반응
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