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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:42 UTC

Update Date

2023-02-21 17:21:09 UTC

HMDB ID

HMDB0031660

Secondary Accession Numbers

HMDB31660

Metabolite Identification

Common Name

Dibutyl sulfide

Description

Dibutyl sulfide belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups. Dibutyl sulfide is a geranium, grassy, and green tasting compound. Dibutyl sulfide has been detected, but not quantified in, several different foods, such as brassicas, cabbages (Brassica oleracea var. capitata), common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make dibutyl sulfide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dibutyl sulfide.

Structure

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

COMPND    HMDB0031660
HETATM    1  C1  UNL     1      -4.369   0.566   0.098  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.881   0.555   0.025  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.345  -0.125   1.293  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.810  -0.135   1.214  1.00  0.00           C  
HETATM    5  S1  UNL     1      -0.425  -1.078  -0.284  1.00  0.00           S  
HETATM    6  C5  UNL     1       1.346  -1.178  -0.595  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.775   0.260  -0.920  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.254   0.330  -1.201  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.048  -0.127  -0.012  1.00  0.00           C  
HETATM   10  H1  UNL     1      -4.824   1.404  -0.434  1.00  0.00           H  
HETATM   11  H2  UNL     1      -4.731  -0.402  -0.347  1.00  0.00           H  
HETATM   12  H3  UNL     1      -4.656   0.646   1.177  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.484   0.047  -0.894  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.454   1.598  -0.034  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.703   0.451   2.145  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.744  -1.153   1.272  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.450  -0.610   2.140  1.00  0.00           H  
HETATM   18  H9  UNL     1      -0.469   0.913   1.143  1.00  0.00           H  
HETATM   19  H10 UNL     1       1.908  -1.597   0.259  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.481  -1.780  -1.510  1.00  0.00           H  
HETATM   21  H12 UNL     1       1.188   0.553  -1.813  1.00  0.00           H  
HETATM   22  H13 UNL     1       1.484   0.860  -0.041  1.00  0.00           H  
HETATM   23  H14 UNL     1       3.493  -0.313  -2.086  1.00  0.00           H  
HETATM   24  H15 UNL     1       3.530   1.369  -1.460  1.00  0.00           H  
HETATM   25  H16 UNL     1       5.135   0.017  -0.188  1.00  0.00           H  
HETATM   26  H17 UNL     1       3.795   0.427   0.910  1.00  0.00           H  
HETATM   27  H18 UNL     1       3.907  -1.229   0.142  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dibutyl sulphide	Generator
1,1'-Thiobis(butane)	HMDB
1,1'-Thiobis-butane	HMDB
1,1'-Thiobisbutane	HMDB
1,1'-Thiobisbutane, 9ci	HMDB
1,1'-Thiodibutane	HMDB
1-(Butylsulfanyl)butane	HMDB
1-Butylsulfanyl-butane	HMDB
5-Thianonane	HMDB
Butyl monosulfide	HMDB
Butyl sulfide	HMDB
Butylthiobutane	HMDB
Di-N-butyl sulfide	HMDB
Di-N-butylsulfide	HMDB
Dibutyl thioether	HMDB
FEMA 2215	HMDB
Hydranal(R)-coulomat CG	HMDB
N-Butyl sulfide	HMDB
N-Butyl-sulfide	HMDB
N-Dibutyl sulfide	HMDB
Thianonane-5	HMDB
Thiononane-5	HMDB
1-(Butylsulphanyl)butane	Generator
Dibutyl sulfide	MeSH

Chemical Formula

C₈H₁₈S

Average Molecular Weight

146.294

Monoisotopic Molecular Weight

146.112921266

IUPAC Name

1-(butylsulfanyl)butane

Traditional Name

di-n-butyl sulfide

CAS Registry Number

544-40-1

SMILES

CCCCSCCCC

InChI Identifier

InChI=1S/C8H18S/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3

InChI Key

HTIRHQRTDBPHNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Dialkylthioethers

Direct Parent

Dialkylthioethers

Alternative Parents

Substituents

Dialkylthioether
Sulfenyl compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031660)
Cell membrane (HMDB: HMDB0031660)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031660)

Source

Endogenous

Endogenous (HMDB: HMDB0031660)

Plant

Plant (HMDB: HMDB0031660)

Exogenous

Food

Food (HMDB: HMDB0031660)

Vegetable

Mushroom

Cabbage

Cabbage (FooDB: FOOD00851)

Brassica

Brassicas (FooDB: FOOD00857)

Exogenous (HMDB: HMDB0031660)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031660)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-80 °C	Not Available
Boiling Point	182.00 to 189.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	39.35 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.034 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.25	ALOGPS
logP	3.66	ChemAxon
logS	-3.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	46.74 m³·mol⁻¹	ChemAxon
Polarizability	19.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	131.982	31661259
DarkChem	[M-H]-	128.771	31661259
DeepCCS	[M+H]+	139.534	30932474
DeepCCS	[M-H]-	137.36	30932474
DeepCCS	[M-2H]-	173.075	30932474
DeepCCS	[M+Na]+	148.079	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	142.2	32859911
AllCCS	[M+Na-2H]-	145.2	32859911
AllCCS	[M+HCOO]-	148.6	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.	6.56 minutes	32390414
Predicted by Siyang on May 30, 2022	18.6194 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2224.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	678.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	244.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	467.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	798.9 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	775.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	240.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1615.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	535.2 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	1492.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	581.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	558.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	569.3 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	17.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibutyl sulfide	CCCCSCCCC	1285.9	Standard polar	33892256
Dibutyl sulfide	CCCCSCCCC	1061.1	Standard non polar	33892256
Dibutyl sulfide	CCCCSCCCC	1079.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dibutyl sulfide EI-B (Non-derivatized)	splash10-0bvi-9000000000-85df5bd2cd49cd3fbdd7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dibutyl sulfide EI-B (Non-derivatized)	splash10-0bvi-9000000000-85df5bd2cd49cd3fbdd7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl sulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9200000000-4ac5b8efb0dff3e6596c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl sulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl sulfide 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 - Dibutyl sulfide 10V, Positive-QTOF	splash10-0002-3900000000-2c8f6b13081b48486190	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 20V, Positive-QTOF	splash10-0a4s-9200000000-992d3bbcb3807fae9d8b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 40V, Positive-QTOF	splash10-0a4l-9000000000-bf8f0c73bc0f8f913b08	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 10V, Negative-QTOF	splash10-0002-3900000000-f55ea7534f55c13ec431	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 20V, Negative-QTOF	splash10-000b-9700000000-667e75592754fbefb1ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 40V, Negative-QTOF	splash10-0543-9000000000-41fcdd8cf3f288f4ab04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 10V, Negative-QTOF	splash10-0002-1900000000-113a422f69c8fa709f6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 20V, Negative-QTOF	splash10-000i-9000000000-c9d6ef78b537068250ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 40V, Negative-QTOF	splash10-001i-9000000000-76139c6d1b08ef1aff99	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 10V, Positive-QTOF	splash10-0udi-4900000000-7220d15d3f4b41d6204c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 20V, Positive-QTOF	splash10-0bt9-9000000000-85639f5ad6a219b5c03a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl sulfide 40V, Positive-QTOF	splash10-06r6-9000000000-c128b229b108306252e3	2021-09-25	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

FDB008320

KNApSAcK ID

Not Available

Chemspider ID

10536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11002

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1018851

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 Dibutyl sulfide (HMDB0031660)

MOL for HMDB0031660 (Dibutyl sulfide)

3D MOL for HMDB0031660 (Dibutyl sulfide)

3D SDF for HMDB0031660 (Dibutyl sulfide)

3D-SDF for HMDB0031660 (Dibutyl sulfide)

PDB for HMDB0031660 (Dibutyl sulfide)

3D PDB for HMDB0031660 (Dibutyl sulfide)

SMILES for HMDB0031660 (Dibutyl sulfide)

INCHI for HMDB0031660 (Dibutyl sulfide)

Structure for HMDB0031660 (Dibutyl sulfide)

3D Structure for HMDB0031660 (Dibutyl sulfide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra