CAS 2257-09-2 Phenethyl Isothiocyanate (HCID 16741)

Overview

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.

Names & identifiers

Preferred name: Phenethyl Isothiocyanate
IUPAC: 2-isothiocyanatoethylbenzene
English name: Phenethyl isothiocyanate
Molecular formula: C9H9NS
Molecular weight: 163.24

Names & synonyms

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

Show more names

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

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 3.5
Topological polar surface area: 44.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 144

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Isothiocyanates

DrugsPharmaceuticals -> Listed in ZINC15

FragrancesFragrance Ingredient (Phenethyl isothiocyanate) -> IFRA transparency List

LogP · 2 items

3.470

3.47

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

Density1.087-1.097

Physicochemical properties

Melting point: 143 · 143~145℃
Boiling point: 75 °C0.25 · 75 °C0.25 mm Hg
Density: 1.094 g/mL · 1.094 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.5888(lit.)
FEMA: 4014 · 4014 | PHENETHYL ISOTHIOCYANATE
FLAVIS Number: 12.193 · 12.193 | Phenethyl isothiocyanate
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: 30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml
form: Liquid
color: Clear colorless to yellow
Specific Gravity: 1.09 · 1.09
Odor: 0.01 % · at 0.01 % in propylene glycol. green horseradish gooseberry watercress
Odor Type: sulfurous
biological source: synthetic
Water Solubility: insoluble
Sensitive: Moisture Sensitive
Merck: 14 · 14,7226
JECFA Number: 1563 · 1563
BRN: 2084162 · 2084162
Cosmetics Ingredients Functions: 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 DataBase Reference: 2257 · 2257-09-2(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): PHENETHYL ISOTHIOCYANATE
EWG's Food Scores: 1 · 1
NCI Dictionary of Cancer Terms: phenethyl isothiocyanate
FDA UNII: 6 U7TFK75KV · 6U7TFK75KV
NCI Drug Dictionary: phenethyl isothiocyanate
NIST Chemistry Reference: Benzene, (2-isothiocyanatoethyl)-(2257-09-2)
EPA Substance Registry System: Benzene, (2-isothiocyanatoethyl)- (2257-09-2)
UNSPSC Code: 85151701 · 85151701
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 302 · H302+H312+H332-H315-H317-H319-H334-H335
Precautionary statements: 261 · P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38-42-42/43
Safety Statements: 23 · 23-26-36-36/37
RIDADR: 2206 · UN 2206 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 9115000 · NX9115000
F: 10 · 10-23
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29309090 · 29309090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Toxicity: 50 in · LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 2 items

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 item

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%)

Toxicology

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

Safety data

F: 10-23
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: NX9115000
ridadr: UN 2206 6.1/PG 3
hs_code: 29309090
Toxicity: LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein)
risk_code: 20/21/22-36/37/38-42-42/43
Signal word: Danger
Symbol(GHS): GHS07,GHS08
hazard_code: Xn
safety_code: 23-26-36-36/37
hazard_class: 8
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H302+H312+H332-H315-H317-H319-H334-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements: P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338

Chemistry & industry

Pharmacology

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 items

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

Uses & manufacturing

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

Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

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

Applications · 4 items

DescriptionPhenethyl 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.

UsesPhenethyl isothiocyanate is an NNK-induced lung tumorigenesis inhibitor.

UsesFlavor 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.

General DescriptionPhenethyl 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.

Preparation methods

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

Upstream & downstream products

Downstream products

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

Suppliers100 total

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]

Additional notes

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.