Benzyl isothiocyanate - ≥98%(GC) , CAS No.622-78-6

CAS: 622-78-6 Cat. No.: B140288 Molecular Weight: 149.21 Beilstein Registry Number: 386135 EC Number: 210-753-9

GRADE & PURITY ≥98%(GC)

Synonyms

Isothiocyanic Acid Benzyl Ester

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Benzyl isothiocyanate is a naturally-occurring constituent of cruciferous vegetables. It has antibacterial properties and its metabolism in man has been investigated. It inhibits chemically induced cancer in animal models
Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.

Specifications

Synonyms

Isothiocyanic Acid Benzyl Ester

Specifications & Purity

≥98%(GC)

Biochemical and Physiological Mechanisms

Antiproliferative, apoptotic agent. Inhibits NF-κB binding to DNA. Suppresses lipid accumulation and macrophage infiltration in tumor tissues. Shows antioxidant and antitumor effects in vivo. Orally active.

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(GC)

Names and Identifiers

• Canonical Smiles: C1=CC=C(C=C1)CN=C=S
• IUPAC Name: isothiocyanatomethylbenzene
• InChIKey: MDKCFLQDBWCQCV-UHFFFAOYSA-N
• INCHI: 1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
• Isomeric SMILES: C1=CC=C(C=C1)CN=C=S
• WGK Germany: 3
• RTECS: NX8250000
• Molecular Weight: 149.21
• Beilstein: 386135
• Reaxy-Rn: 386135
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=386135&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Isothiocyanates Propargyl-type 1,3-dipolar organic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Monocyclic benzene moiety - Isothiocyanate - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (2 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MIF Tchem Macrophage migration inhibitory factor (3 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSTM1 Tbio Glutathione S-transferase Mu 1 (61 Activities)

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MIF Tchem Macrophage migration inhibitory factor (979 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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CTSB Tchem Cathepsin B (3822 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

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GSTK1 Tchem Glutathione S-transferase kappa 1 (56 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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Caco-2 (12174 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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LoVo (4724 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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T98G (1524 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Cyp2b1 Cytochrome P450 2B1 (145 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Mus musculus (284745 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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4T1 (1737 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

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Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

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Sclerotinia sclerotiorum (877 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Meloidogyne javanica (98 Activities)

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groL GroEL/GroES (1042 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Hydrolyzes in water.
• Sensitivity: Light & Moisture Sensitive.
• Refractive Index: 1.6020-1.6050
• Flash Point(°F): >230 °F
• Flash Point(°C): >110 °C
• Boil Point(°C): 242-243 °C
• Molecular Weight: 149.210 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 149.03 Da
• Monoisotopic Mass: 149.03 Da
• Topological Polar Surface Area: 44.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 132.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Ma Yinzheng, Wen Yingying, Chen Jinping, Zhang Yunxia, Zhang Haiying, Sui Jinlei, Yi Guohui, He Xiaowen.  (2021)  Rapid and sensitive analysis of benzyl isothiocyanate in peel, pulp, and seeds of Carica papaya Linn. by headspace gas chromatography-mass spectrometry.  SN Applied Sciences,  3  (3): (1-9).  [PMID:] [10.1007/s42452-021-04356-3]

2. Xia Li, Maowei Ni, Xiaoling Xu, Wei Chen.  (2020)  Characterisation of naturally occurring isothiocyanates as glutathione reductase inhibitors.  JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY,      [PMID:32951477] [10.1080/14756366.2020.1822828]

3. Zitong Ge, Xiaxin Du, Jianan Liu, Junya Zhu, Hongshun Hao, Jingran Bi, Hongman Hou, Gongliang Zhang.  (2024)  Benzyl isothiocyanate suppresses biofilms and virulence factors as a quorum sensing inhibitor in Pseudomonas fluorescens.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2024.116387]