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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:12 UTC

Update Date

2023-02-21 17:18:49 UTC

HMDB ID

HMDB0029569

Secondary Accession Numbers

HMDB29569

Metabolite Identification

Common Name

Dibutyl disulfide

Description

Dibutyl disulfide, also known as 5,6-dithiadecane, belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups. Based on a literature review a small amount of articles have been published on Dibutyl disulfide.

Structure

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

COMPND    HMDB0029569
HETATM    1  C1  UNL     1       4.303  -0.310   0.414  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.014   0.944  -0.367  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.579   1.403  -0.215  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.605   0.353  -0.699  1.00  0.00           C  
HETATM    5  S1  UNL     1      -0.076   0.999  -0.476  1.00  0.00           S  
HETATM    6  S2  UNL     1      -1.412  -0.537  -1.171  1.00  0.00           S  
HETATM    7  C5  UNL     1      -1.834  -1.624   0.185  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.670  -0.908   1.211  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.979  -0.410   0.690  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.867   0.575  -0.447  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.723  -1.122  -0.028  1.00  0.00           H  
HETATM   12  H2  UNL     1       5.386  -0.531   0.265  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.151  -0.184   1.499  1.00  0.00           H  
HETATM   14  H4  UNL     1       4.291   0.764  -1.406  1.00  0.00           H  
HETATM   15  H5  UNL     1       4.649   1.752   0.084  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.447   2.286  -0.870  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.378   1.675   0.830  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.749  -0.618  -0.192  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.755   0.271  -1.808  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.445  -2.467  -0.257  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.959  -2.134   0.636  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.791  -1.562   2.100  1.00  0.00           H  
HETATM   23  H13 UNL     1      -2.104  -0.017   1.597  1.00  0.00           H  
HETATM   24  H14 UNL     1      -4.652  -1.262   0.385  1.00  0.00           H  
HETATM   25  H15 UNL     1      -4.545   0.129   1.492  1.00  0.00           H  
HETATM   26  H16 UNL     1      -4.799   1.219  -0.485  1.00  0.00           H  
HETATM   27  H17 UNL     1      -3.863   0.050  -1.436  1.00  0.00           H  
HETATM   28  H18 UNL     1      -3.031   1.263  -0.367  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6
CONECT    6    7
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dibutyl disulphide	Generator
1-(Butyldisulfanyl)butane	HMDB
5,6-Dithiadecane	HMDB
Butyl disulfide (8ci)	HMDB
N-Butyl disulfide	HMDB
1-(Butyldisulphanyl)butane	HMDB

Chemical Formula

C₈H₁₈S₂

Average Molecular Weight

178.359

Monoisotopic Molecular Weight

178.084991956

IUPAC Name

1-(butyldisulfanyl)butane

Traditional Name

dibutyl disulfide

CAS Registry Number

629-45-8

SMILES

CCCCSSCCCC

InChI Identifier

InChI=1S/C8H18S2/c1-3-5-7-9-10-8-6-4-2/h3-8H2,1-2H3

InChI Key

CUDSBWGCGSUXDB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Organic disulfides

Sub Class

Dialkyldisulfides

Direct Parent

Dialkyldisulfides

Alternative Parents

Substituents

Dialkyldisulfide
Sulfenyl compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Sulfurous

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029569)
Cell membrane (HMDB: HMDB0029569)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029569)

Source

Endogenous

Endogenous (HMDB: HMDB0029569)

Plant

Plant (HMDB: HMDB0029569)

Exogenous

Food

Food (HMDB: HMDB0029569)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0029569)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	229.00 to 233.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4.29 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.207 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	4.71	ALOGPS
logP	3.95	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	7	ChemAxon
Refractivity	54.84 m³·mol⁻¹	ChemAxon
Polarizability	22.31 Å³	ChemAxon
Number of Rings	0	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]+	139.24	31661259
DarkChem	[M-H]-	136.423	31661259
DeepCCS	[M+H]+	141.97	30932474
DeepCCS	[M-H]-	139.639	30932474
DeepCCS	[M-2H]-	175.53	30932474
DeepCCS	[M+Na]+	150.689	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	145.0	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	147.5	32859911
AllCCS	[M+Na-2H]-	150.1	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibutyl disulfide	CCCCSSCCCC	1560.4	Standard polar	33892256
Dibutyl disulfide	CCCCSSCCCC	1302.6	Standard non polar	33892256
Dibutyl disulfide	CCCCSSCCCC	1299.6	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 - Dibutyl disulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9200000000-5e911cd48c68a97114b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl 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 - Dibutyl disulfide 10V, Positive-QTOF	splash10-004i-3900000000-02cebd8d1cba749353bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 20V, Positive-QTOF	splash10-0ab9-9500000000-0da14f5b22a52da6af7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 40V, Positive-QTOF	splash10-052f-9000000000-d3cb488d934df0be6a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 10V, Negative-QTOF	splash10-004i-1900000000-70eab60cc634632a7159	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 20V, Negative-QTOF	splash10-000i-9200000000-69d30a621f2d70cb193f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 40V, Negative-QTOF	splash10-0a4u-9200000000-4637a41171b95ecff533	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 10V, Positive-QTOF	splash10-052r-9100000000-3d93fb52e4f0d81ed783	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 20V, Positive-QTOF	splash10-0a4r-9000000000-848f876822f032bda217	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 40V, Positive-QTOF	splash10-0a4i-9000000000-84f339c68f943bf6cb19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 10V, Negative-QTOF	splash10-000i-9000000000-a5b26651901c6ca34934	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 20V, Negative-QTOF	splash10-000i-9000000000-9ed95ef58c3ccb0ac6f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl disulfide 40V, Negative-QTOF	splash10-01qi-9000000000-c23f4f9ab3b61a3c0b2b	2021-09-24	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB000724

KNApSAcK ID

C00054009

Chemspider ID

11880

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12386

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056681

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 disulfide (HMDB0029569)

MOL for HMDB0029569 (Dibutyl disulfide)

3D MOL for HMDB0029569 (Dibutyl disulfide)

3D SDF for HMDB0029569 (Dibutyl disulfide)

3D-SDF for HMDB0029569 (Dibutyl disulfide)

PDB for HMDB0029569 (Dibutyl disulfide)

3D PDB for HMDB0029569 (Dibutyl disulfide)

SMILES for HMDB0029569 (Dibutyl disulfide)

INCHI for HMDB0029569 (Dibutyl disulfide)

Structure for HMDB0029569 (Dibutyl disulfide)

3D Structure for HMDB0029569 (Dibutyl disulfide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra