Phenethyl Isothiocyanate (HCID 16741)

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Phenethyl Isothiocyanate
IUPAC: 2-isothiocyanatoethylbenzene
Lokaler Name: Phenethylisothiocyanat
Englischer Name: Phenethyl isothiocyanate
Summenformel: C9H9NS
Molmasse: 163.24

Namen und Synonyme

Phenethyl isothiocyanate2-Phenylethyl isothiocyanate2257-09-2Phenylethyl isothiocyanate(2-Isothiocyanatoethyl)benzene2-isothiocyanatoethylbenzeneBenzene, (2-isothiocyanatoethyl)-PEITCPhenylaethylsenfoelPHENETHYLISOTHIOCYANATEbeta-Phenylethyl isothiocyanateISOTHIOCYANIC ACID, PHENETHYL ESTER

Weitere Namen anzeigen

(?)-EquolAKOS B0163231-(2-ISOTHIOCY7-DihydroxyisoflavanphenylethylmustardoilPhenethyl mustard oil

DTXSID50211206U7TFK75KVCHEBI:351346NSC-87868beta-Phenethyl isothiocyanateDTXCID901120FEMA NO. 4014NSC87868

Datenbank-Bezeichner

CAS: 2257-09-2
PubChem CID: 16741
DTXSID: DTXSID5021120
ChEMBL: CHEMBL151649
ChEBI: CHEBI:351346
UNII: 6U7TFK75KV
EC Number: 218-855-5
Nikkaji: J41.504I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,5
Polarare Oberfläche (TPSA): 44,5 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 3
Schwere Atome: 11
Formalladung: 0
Komplexität: 144

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Isothiocyanates

DrugsPharmaceuticals -> Listed in ZINC15

FragrancesFragrance Ingredient (Phenethyl isothiocyanate) -> IFRA transparency List

LogP · 2 Einträge

3.470

3.47

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.087-1.097

Physikochemische Eigenschaften

Schmelzpunkt: 143 · 143~145℃
Siedepunkt: 75 °C0.25 · 75 °C0.25 mm Hg
Dichte: 1.094 g/mL · 1.094 g/mL at 25 °C(lit.)
Brechungsindex: 20 · n20/D 1.5888(lit.)
FEMA: 4014 · 4014 | PHENETHYL ISOTHIOCYANATE
Flammpunkt: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
Löslichkeit: 30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml
Aggregatzustand: Liquid
Farbe: Clear colorless to yellow
Wichte: 1.09 · 1.09
Geruch (Odor): 0.01 % · at 0.01 % in propylene glycol. green horseradish gooseberry watercress
Geruchsart: sulfurous
Biologische Quelle: synthetic
Wasserlöslichkeit: insoluble
Merck: 14 · 14,7226
JECFA Number: 1563 · 1563
BRN: 2084162 · 2084162
Kosmetik-Inhaltsstoffe Funktionen: PERFUMING
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
CAS Datenbank: 2257 · 2257-09-2(CAS DataBase Reference)
NIST chemische Informationen: Benzene, (2-isothiocyanatoethyl)-(2257-09-2)
EPA chemische Informationen: Benzene, (2-isothiocyanatoethyl)- (2257-09-2)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 · 1 Eintrag

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%)

Toxikologische Informationen

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Sicherheitsdaten

F: 10-23
wgk: 3
tsca: TSCA listed
ridadr: UN 2206 6.1/PG 3
hs_code: 29309090
RTECS-Nr.: NX9115000
risk_code: 20/21/22-36/37/38-42-42/43
Toxizität: LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein)
hazard_code: Xn
safety_code: 23-26-36-36/37
hazard_class: 8
packing_group: III
Speicherklasse: 10 - Combustible liquids
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3

Chemie und Industrie

Pharmakologische Informationen

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 · 3 Einträge

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

Verwendung und Herstellung

UsesPresent in cruciferous vegetables; Used as a flavor (hot/burning taste in horseradish); [Merck Index] Used as a flavoring agent; [FDA]

Use Classification · 3 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationBenzene, (2-isothiocyanatoethyl)-: ACTIVE

Anwendungen · 2 Einträge

BeschreibungPhenethyl 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.

VerwendenFlavor 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.

Darstellung

synthetischePrepared by hydrolysis of gluconasturtiin, an abundant natural product present in cruciferous vegetables.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE N6-{[(2-Phenylethyl)amino]carbonothioyl}lysine (PEITC-Lys)

Anbieter50 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

苏州道澜生物医药科技有限公司15952404857 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: 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.