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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:39 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034273
Secondary Accession Numbers
  • HMDB34273
Metabolite Identification
Common NameBenzyl thiocyanate
DescriptionBenzyl thiocyanate, also known as solvat 14 or tropeolin, belongs to the class of organic compounds known as benzyl thiocyanates. These are aromatic compounds containing an thiocyanate group that is S-substituted to a benzyl group. Benzyl thiocyanate has been detected, but not quantified in, brassicas and garden cresses (Lepidium sativum). This could make benzyl thiocyanate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Benzyl thiocyanate.
Structure
Data?1563862538
Synonyms
ValueSource
alpha-ThiocyanatotolueneChEBI
Solvat 14ChEBI
Thiocyanic acid benzyl esterChEBI
Thiocyanic acid, phenylmethyl esterChEBI
TropeolinChEBI
a-ThiocyanatotolueneGenerator
Α-thiocyanatotolueneGenerator
Thiocyanate benzyl esterGenerator
Thiocyanate, phenylmethyl esterGenerator
Benzyl thiocyanic acidGenerator
alpha -ThiocyanatotolueneHMDB
alpha-thiocyanato-TolueneHMDB
Benzyl rhodanideHMDB
Benzyl-thiocyanateHMDB
BenzylrhodonidHMDB
BenzylthiocyanateHMDB, MeSH
Phenylmethyl thiocyanateHMDB
Phenylmethyl thiocyanate, 9ciHMDB
Thiocyanic acid, benzyl esterHMDB
Chemical FormulaC8H7NS
Average Molecular Weight149.213
Monoisotopic Molecular Weight149.029919919
IUPAC Name(benzylsulfanyl)carbonitrile
Traditional Namebenzyl thiocyanate
CAS Registry Number3012-37-1
SMILES
N#CSCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NS/c9-7-10-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeyABNDFSOIUFLJAH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl thiocyanates. These are aromatic compounds containing an thiocyanate group that is S-substituted to a benzyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl thiocyanates
Direct ParentBenzyl thiocyanates
Alternative Parents
Substituents
  • Benzyl thiocyanate
  • Sulfenyl compound
  • Thiocyanate
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 - 42 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1528 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.99Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.68 g/LALOGPS
logP2.18ALOGPS
logP2.51ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.66 m³·mol⁻¹ChemAxon
Polarizability15.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.72431661259
DarkChem[M-H]-126.61631661259
DeepCCS[M+H]+125.32430932474
DeepCCS[M-H]-122.27530932474
DeepCCS[M-2H]-159.1330932474
DeepCCS[M+Na]+134.1730932474
AllCCS[M+H]+128.332859911
AllCCS[M+H-H2O]+123.832859911
AllCCS[M+NH4]+132.532859911
AllCCS[M+Na]+133.732859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-130.432859911
AllCCS[M+HCOO]-132.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzyl thiocyanateN#CSCC1=CC=CC=C12232.1Standard polar33892256
Benzyl thiocyanateN#CSCC1=CC=CC=C11345.5Standard non polar33892256
Benzyl thiocyanateN#CSCC1=CC=CC=C11373.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzyl thiocyanate GC-EI-TOF (Non-derivatized)splash10-0006-9000000000-68f98454bb5712d637cc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl thiocyanate GC-EI-TOF (Non-derivatized)splash10-0006-9000000000-68f98454bb5712d637cc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl thiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-ef35bd6bfa9dc0a361222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl thiocyanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 10V, Positive-QTOFsplash10-0uk9-1900000000-fb499fc651424df158642016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 20V, Positive-QTOFsplash10-0006-9600000000-6f653a1ae3a4b8cdc82b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 40V, Positive-QTOFsplash10-0006-9300000000-828cc6935e8d681302492016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 10V, Negative-QTOFsplash10-052b-6900000000-4da6b1c520d7ae062cfe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 20V, Negative-QTOFsplash10-0a4i-9100000000-374a7bfeeaae03ccc56a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-16384896c6f34035bb742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 10V, Positive-QTOFsplash10-0006-9000000000-47d2029de8830d06652e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 20V, Positive-QTOFsplash10-0006-9400000000-e9634d68b339823f83092021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 40V, Positive-QTOFsplash10-00kf-9100000000-0ffd982ecdde3e549a032021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 10V, Negative-QTOFsplash10-0002-0900000000-3562640e821f8add3ef42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 20V, Negative-QTOFsplash10-00di-0900000000-ca94040d24d277b7848b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl thiocyanate 40V, Negative-QTOFsplash10-004i-9100000000-2fde917c979c43b36e1c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012606
KNApSAcK IDC00054093
Chemspider ID17163
KEGG Compound IDC02660
BioCyc IDCPD-65
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18170
PDB IDNot Available
ChEBI ID16017
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1222631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tellez MR, Khan IA, Kobaisy M, Schrader KK, Dayan FE, Osbrink W: Composition of the essential oil of Lepidium meyenii (Walp). Phytochemistry. 2002 Sep;61(2):149-55. [PubMed:12169308 ]
  2. Batanero B, Barba F, Martin A: Preparation of 2,6-dimethyl-4-arylpyridine- 3,5-dicarbonitrile: a paired electrosynthesis. J Org Chem. 2002 Apr 5;67(7):2369-71. [PubMed:11925258 ]
  3. Iwai N, Ebata T, Nagura H, Kitazume T, Nagai K, Wachi M: Structure-activity relationship of S-benzylisothiourea derivatives to induce spherical cells in Escherichia coli. Biosci Biotechnol Biochem. 2004 Nov;68(11):2265-9. [PubMed:15564663 ]
  4. Zhang Z, Liebeskind LS: Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids. Org Lett. 2006 Sep 14;8(19):4331-3. [PubMed:16956219 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .