기본 정보
- 표준 SMILES
S=C=NCCc1ccccc1- InChIKey
IZJDOKYDEWTZSO-UHFFFAOYSA-N- 분자식
- C9H9NS
- 평균 분자량
- 163.24 g/mol
- 단동위원소 질량
- 163.04557029
개요
Phenethyl isothiocyanate is an isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties. It has a role as a metabolite, an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor and an antineoplastic agent.
이름 및 식별자
- 우선 이름
- Phenethyl Isothiocyanate
- IUPAC
- 2-isothiocyanatoethylbenzene
- 영어명
- Phenethyl isothiocyanate
- 분자식
- C9H9NS
- 분자량
- 163.24
이름 및 동의어
Phenethyl isothiocyanate2-Phenylethyl isothiocyanate2257-09-2Phenylethyl isothiocyanate(2-Isothiocyanatoethyl)benzene2-isothiocyanatoethylbenzeneBenzene, (2-isothiocyanatoethyl)-PEITCPhenylaethylsenfoelPHENETHYLISOTHIOCYANATEbeta-Phenylethyl isothiocyanateISOTHIOCYANIC ACID, PHENETHYL ESTER
이름 더 보기
(?)-EquolAKOS B0163231-(2-ISOTHIOCY7-DihydroxyisoflavanphenylethylmustardoilPhenethyl mustard oil
DTXSID50211206U7TFK75KVCHEBI:351346NSC-87868beta-Phenethyl isothiocyanateDTXCID901120FEMA NO. 4014NSC87868
데이터베이스 식별자
- CAS
2257-09-2- PubChem CID
- 16741
- DTXSID
DTXSID5021120- ChEMBL
CHEMBL151649- ChEBI
CHEBI:351346- UNII
- 6U7TFK75KV
- EC Number
- 218-855-5
- Nikkaji
- J41.504I
물성
구조 계산 물성
- XLogP
- 3.5
- 극성 표면적
- 44.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 11
- 형식 전하
- 0
- 복잡도
- 144
실험 및 물리화학적 성질
Chemical ClassesNitrogen Compounds -> Isothiocyanates
DrugsPharmaceuticals -> Listed in ZINC15
FragrancesFragrance Ingredient (Phenethyl isothiocyanate) -> IFRA transparency List
LogP
3.470
3.47
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.087-1.097
Flavoring AgentsEU Flavoring substances
Solubility
110 mg/L @ 20 °C (exp)
Insoluble in water; Soluble in triacetin and heptane
Soluble (in ethanol)
Boiling Point
139.00 to 140.00 °C. @ 11.00 mm Hg
139-140 °C
Vapor Pressure0.01 [mmHg]
Refractive Index1.586-1.590
Physical Description
Colorless to pale yellow liquid; [Merck Index] Clear colorless liquid; [Sigma-Aldrich MSDS]
Nearly Colourless liquid; Strong green irritating aroma
물리화학적 성질
- 녹는점
- 143 · 143~145℃
- 끓는 점
- 75 °C0.25 · 75 °C0.25 mm Hg
- 밀도
- 1.094 g/mL · 1.094 g/mL at 25 °C(lit.)
- 굴절률
- 20 · n20/D 1.5888(lit.)
- FEMA
- 4014 · 4014 | PHENETHYL ISOTHIOCYANATE
- 인화점
- 230 °F · >230 °F
- 저장 조건
- 2 · 2-8°C
- 용해도
- 30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml
- 물리적 상태
- 액체
- 색상
- 무색~황색으로 투명함
- Specific Gravity
- 1.09 · 1.09
- 냄새
- 0.01 % · 프로필렌 글리콜 중 0.01%. 녹색 양 고추 냉이 구스베리 물냉이
- 냄새 유형
- 유황의
- 생물학적 소스
- synthetic
- 수용성
- 불용성
- Merck
- 14 · 14,7226
- JECFA Number
- 1563 · 1563
- BRN
- 2084162 · 2084162
- 화장품 원료 기능
- 향수
- InChI
- 1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
- InChIKey
- IZJDOKYDEWTZSO-UHFFFAOYSA-N
- SMILES
- S=C=NCCc1ccccc1
- LogP
- 3.47 · 3.47
- NIST
- Benzene, (2-isothiocyanatoethyl)-(2257-09-2)
- EPA
- Benzene, (2-isothiocyanatoethyl)- (2257-09-2)
화학적 성질
Phenethyl isothiocyanate has a strong green irritating odor.
안전 및 규제
GHS 분류
GHS Classification
Warning
H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1643 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory Information
Chemical: Benzene, (2-isothiocyanatoethyl)-
Benzene, (2-isothiocyanatoethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Chemicals with limited data availability that are used in fragrances: Human health tier II assessment
Hazards Summary
Causes inflammation or scarring of the bladder in acute oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; May cause skin and respiratory sensitization; Harmful by ingestion, inhalation, and skin absorption; [Sigma-Aldrich MSDS] See Methyl isothiocyanate and Phenyl isothiocyanate.
Hazard Classes and CategoriesAcute Tox. 4 (> 99.9%)
독성 정보
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NX9115000
- ridadr
- UN 2206 6.1/PG 3
- 독성
- LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein)
- HS 번호
- 29309090
- risk_code
- 20/21/22-36/37/38-42-42/43
- hazard_code
- Xn
- safety_code
- 23-26-36-36/37
- 포장분류
- III
- 위험 등급
- 8
- F 고인화성물질
- 10-23
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- 스토리지 클래스
- 10 - Combustible liquids
화학 및 산업
약리 정보
Metabolism/MetabolitesPhenethyl isothiocyanate has known human metabolites that include (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(2-phenylethylcarbamothioylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid.
MeSH Pharmacological Classification
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Cellular LocationsMembrane
용도 및 제조
UsesPresent in cruciferous vegetables; Used as a flavor (hot/burning taste in horseradish); [Merck Index] Used as a flavoring agent; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationBenzene, (2-isothiocyanatoethyl)-: ACTIVE
응용 분야
개요Phenethyl isothiocyanate is a naturally occurring isothiocyanate in cruciferous vegetables. Phenethyl isothiocyanate is a chemopreventive agent. It inhibits cancer cell growth by arresting the cell cycle and inducing apoptosis in various human cancer cell models.
용도Flavor ingredient; provides the hot or burning sensation in horseradish. Phenethyl isothiocyanate (PEITC)，one of the major compounds from dietary cruciferousvegetables，has been found to have antitumor properties and therefore could generate special interest for the development of chemopreventive andor chemotherapeutic agent for human cancers.
일반 설명Phenethyl isothiocyanate, an organic isothiocyanate, is a cruciferous vegetable ingredient present as a glucosinolate in cabbage, turnips, radishes, etc. It is a well-known chemopreventive agent reported to be effective against cancers affecting the lung, breast, pancreas, prostate and so on.
제조 방법
Prepared by hydrolysis of gluconasturtiin, an abundant natural product present in cruciferous vegetables.
상·하류 제품 정보
하류 제품
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추가 설명
정의ChEBI: An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.
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