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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:09:03 UTC

Update Date

2023-02-21 17:28:23 UTC

HMDB ID

HMDB0040590

Secondary Accession Numbers

HMDB40590

Metabolite Identification

Common Name

Benzyl methyl disulfide

Description

Benzyl methyl disulfide 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. Benzyl methyl disulfide is a cabbage, green, and metallic tasting compound. Benzyl methyl disulfide has been detected, but not quantified in, a few different foods, such as cocoa and cocoa products, cocoa beans (Theobroma cacao), and nuts. This could make benzyl methyl disulfide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl methyl disulfide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzyl methyl disulphide	Generator
Benzyldithiomethane	HMDB
Disulfide, benzyl methyl	HMDB
Disulfide, methyl phenylmethyl	HMDB
FEMA 3504	HMDB
Methyl benzyl disulfide	HMDB
Methyl phenylmethyl disulfide	HMDB
Methyl phenylmethyl disulfide, 9ci	HMDB
Nonsymmetrical disulfide analog	HMDB
[(Methyldisulfanyl)methyl]benzene	HMDB
[(Methyldisulphanyl)methyl]benzene	Generator

Chemical Formula

C₈H₁₀S₂

Average Molecular Weight

170.295

Monoisotopic Molecular Weight

170.0223917

IUPAC Name

[(methyldisulfanyl)methyl]benzene

Traditional Name

disulfide, methyl phenylmethyl

CAS Registry Number

699-10-5

SMILES

CSSCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H10S2/c1-9-10-7-8-5-3-2-4-6-8/h2-6H,7H2,1H3

InChI Key

NWYGPVZOBBHKLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Dialkyldisulfide
Organic disulfide
Sulfenyl compound
Hydrocarbon derivative
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0040590)
Cell membrane (HMDB: HMDB0040590)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040590)

Source

Exogenous

Exogenous (HMDB: HMDB0040590)

Food

Food (HMDB: HMDB0040590)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0040590)
Theobroma cacao (HMDB: HMDB0040590)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040590)

Biological role

Nutrient (HMDB: HMDB0040590)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61.00 to 62.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	195.00 to 197.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	53.61 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.633 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.096 g/L	ALOGPS
logP	2.83	ALOGPS
logP	3.05	ChemAxon
logS	-3.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.73 m³·mol⁻¹	ChemAxon
Polarizability	18.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.162	31661259
DarkChem	[M-H]-	132.038	31661259
DeepCCS	[M+H]+	129.055	30932474
DeepCCS	[M-H]-	125.981	30932474
DeepCCS	[M-2H]-	162.955	30932474
DeepCCS	[M+Na]+	137.857	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	127.5	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.1	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.01 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4844 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2000.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	491.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	310.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	567.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	586.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	126.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1173.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1239.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	482.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	396.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	60.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzyl methyl disulfide	CSSCC1=CC=CC=C1	2135.4	Standard polar	33892256
Benzyl methyl disulfide	CSSCC1=CC=CC=C1	1368.8	Standard non polar	33892256
Benzyl methyl disulfide	CSSCC1=CC=CC=C1	1424.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl methyl disulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-c1cb11117a79d640d45a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl methyl disulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 10V, Positive-QTOF	splash10-00di-3900000000-c44cabb1ee0883d23c0f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 20V, Positive-QTOF	splash10-00dl-7900000000-6d14c91312878f161afd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 40V, Positive-QTOF	splash10-0006-9000000000-12d2672101f44fa56af4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 10V, Negative-QTOF	splash10-016r-6900000000-707ae5307f60ce98e1ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 20V, Negative-QTOF	splash10-00dm-9600000000-f1fd6845062cc25fb800	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 40V, Negative-QTOF	splash10-00di-9700000000-a5156683fbba1a04486f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 10V, Positive-QTOF	splash10-0006-9000000000-47d2029de8830d06652e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 20V, Positive-QTOF	splash10-006x-9500000000-4e1174a62dfe08cd0387	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 40V, Positive-QTOF	splash10-0006-9000000000-017e4830edf72dfd1d5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 10V, Negative-QTOF	splash10-00xs-4900000000-f1cfc925ab5940b2f2c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 20V, Negative-QTOF	splash10-0002-9000000000-74bb5066a347a9572547	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl methyl disulfide 40V, Negative-QTOF	splash10-004i-9200000000-09e9bb32e1c8379b9786	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020373

KNApSAcK ID

Not Available

Chemspider ID

12254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12779

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benzyl methyl disulfide (HMDB0040590)

MOL for HMDB0040590 (Benzyl methyl disulfide)

3D MOL for HMDB0040590 (Benzyl methyl disulfide)

3D SDF for HMDB0040590 (Benzyl methyl disulfide)

3D-SDF for HMDB0040590 (Benzyl methyl disulfide)

PDB for HMDB0040590 (Benzyl methyl disulfide)

3D PDB for HMDB0040590 (Benzyl methyl disulfide)

SMILES for HMDB0040590 (Benzyl methyl disulfide)

INCHI for HMDB0040590 (Benzyl methyl disulfide)

Structure for HMDB0040590 (Benzyl methyl disulfide)

3D Structure for HMDB0040590 (Benzyl methyl disulfide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra