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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:52:43 UTC

Update Date

2023-02-21 17:28:11 UTC

HMDB ID

HMDB0040348

Secondary Accession Numbers

HMDB40348

Metabolite Identification

Common Name

1,8-Octanedithiol

Description

1,8-Octanedithiol belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. 1,8-Octanedithiol is an earthy, meaty, and mushroom tasting compound. Based on a literature review a significant number of articles have been published on 1,8-Octanedithiol.

Structure

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

COMPND    HMDB0040348
HETATM    1  S1  UNL     1      -3.970   1.291   1.074  1.00  0.00           S  
HETATM    2  C1  UNL     1      -3.261   0.616  -0.451  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.311  -0.521  -0.115  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.228   0.022   0.755  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.215  -1.012   1.160  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.491  -1.643  -0.000  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.231  -0.607  -0.810  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.273   0.126  -0.011  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.961   1.148  -0.928  1.00  0.00           C  
HETATM   10  S2  UNL     1       4.205   1.996   0.099  1.00  0.00           S  
HETATM   11  H1  UNL     1      -4.963   2.227   0.715  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.680   1.397  -1.000  1.00  0.00           H  
HETATM   13  H3  UNL     1      -4.109   0.260  -1.084  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.967  -0.985  -1.042  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.880  -1.291   0.475  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.715   0.366   1.709  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.761   0.927   0.323  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.755  -1.769   1.766  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.526  -0.555   1.843  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.164  -2.213  -0.662  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.290  -2.306   0.445  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.738  -1.073  -1.669  1.00  0.00           H  
HETATM   23  H13 UNL     1       0.494   0.118  -1.247  1.00  0.00           H  
HETATM   24  H14 UNL     1       3.073  -0.613   0.244  1.00  0.00           H  
HETATM   25  H15 UNL     1       1.883   0.623   0.893  1.00  0.00           H  
HETATM   26  H16 UNL     1       2.168   1.841  -1.265  1.00  0.00           H  
HETATM   27  H17 UNL     1       3.420   0.562  -1.738  1.00  0.00           H  
HETATM   28  H18 UNL     1       5.227   1.066   0.358  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8-Dimercaptooctane	HMDB
1,8-Octamethylenedithiol	HMDB
FEMA 3514	HMDB
NanoThinks(TM) thio8	HMDB
Octamethylene dimercaptan	HMDB
Octane-1,8-dithiol	HMDB
1,8-Octanedithiol	MeSH

Chemical Formula

C₈H₁₈S₂

Average Molecular Weight

178.359

Monoisotopic Molecular Weight

178.084991956

IUPAC Name

octane-1,8-dithiol

Traditional Name

octane-1,8-dithiol

CAS Registry Number

1191-62-4

SMILES

SCCCCCCCCS

InChI Identifier

InChI=1S/C8H18S2/c9-7-5-3-1-2-4-6-8-10/h9-10H,1-8H2

InChI Key

PGTWZHXOSWQKCY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiols

Sub Class

Alkylthiols

Direct Parent

Alkylthiols

Alternative Parents

Hydrocarbon derivatives

Substituents

Alkylthiol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0040348)
Cell membrane (HMDB: HMDB0040348)

Source

Exogenous

Exogenous (HMDB: HMDB0040348)

Food

Food (HMDB: HMDB0040348)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040348)

Biological role

Nutrient (HMDB: HMDB0040348)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	0.9 °C	Not Available
Boiling Point	142.00 °C. @ 30.00 mm Hg	The Good Scents Company Information System
Water Solubility	15.79 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.214 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.63	ALOGPS
logP	3.65	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.52 m³·mol⁻¹	ChemAxon
Polarizability	22.77 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]+	140.036	31661259
DarkChem	[M-H]-	137.403	31661259
DeepCCS	[M+H]+	146.823	30932474
DeepCCS	[M-H]-	144.465	30932474
DeepCCS	[M-2H]-	180.262	30932474
DeepCCS	[M+Na]+	155.52	30932474
AllCCS	[M+H]+	139.3	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	142.7	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	150.2	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	155.6	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.	6.05 minutes	32390414
Predicted by Siyang on May 30, 2022	21.2394 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	61.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3226.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	791.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	284.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	547.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	857.2 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	983.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	882.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1833.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	494.6 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	1709.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	697.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	508.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	849.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	790.2 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	57.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,8-Octanedithiol	SCCCCCCCCS	1890.9	Standard polar	33892256
1,8-Octanedithiol	SCCCCCCCCS	1450.7	Standard non polar	33892256
1,8-Octanedithiol	SCCCCCCCCS	1469.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,8-Octanedithiol,1TMS,isomer #1	C[Si](C)(C)SCCCCCCCCS	1683.8	Semi standard non polar	33892256
1,8-Octanedithiol,1TMS,isomer #1	C[Si](C)(C)SCCCCCCCCS	1676.6	Standard non polar	33892256
1,8-Octanedithiol,2TMS,isomer #1	C[Si](C)(C)SCCCCCCCCS[Si](C)(C)C	1898.9	Semi standard non polar	33892256
1,8-Octanedithiol,2TMS,isomer #1	C[Si](C)(C)SCCCCCCCCS[Si](C)(C)C	1958.6	Standard non polar	33892256
1,8-Octanedithiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SCCCCCCCCS	1933.1	Semi standard non polar	33892256
1,8-Octanedithiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SCCCCCCCCS	1880.0	Standard non polar	33892256
1,8-Octanedithiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SCCCCCCCCS[Si](C)(C)C(C)(C)C	2377.5	Semi standard non polar	33892256
1,8-Octanedithiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SCCCCCCCCS[Si](C)(C)C(C)(C)C	2356.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,8-Octanedithiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbj-9500000000-af78363dfcff0a3799c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,8-Octanedithiol 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 - 1,8-Octanedithiol 10V, Positive-QTOF	splash10-004i-0900000000-c94427f85c17b17ad00a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 20V, Positive-QTOF	splash10-004i-2900000000-27c7841c81b128d4e243	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 40V, Positive-QTOF	splash10-06tf-9100000000-e811ffb3082f6dfc3878	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 10V, Negative-QTOF	splash10-004i-1900000000-80f0f3b132888c64fd72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 20V, Negative-QTOF	splash10-004i-2900000000-0eefeff37be6dbe90780	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 40V, Negative-QTOF	splash10-001i-9000000000-a9941013ea50027341a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 10V, Negative-QTOF	splash10-004i-0900000000-4453af1ef9e4f3b3433c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 20V, Negative-QTOF	splash10-004i-0900000000-91a3611fc7c79ef569ff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 40V, Negative-QTOF	splash10-0059-9700000000-06292075da950073a9e4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 10V, Positive-QTOF	splash10-004j-3900000000-08c4da773672a50eba8f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 20V, Positive-QTOF	splash10-0230-9200000000-a10fcfbc9ddae4d98543	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,8-Octanedithiol 40V, Positive-QTOF	splash10-0007-9000000000-44df27496f7f06f693bd	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+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

FDB020073

KNApSAcK ID

C00056582

Chemspider ID

13838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14493

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036621

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 1,8-Octanedithiol (HMDB0040348)

MOL for HMDB0040348 (1,8-Octanedithiol)

3D MOL for HMDB0040348 (1,8-Octanedithiol)

3D SDF for HMDB0040348 (1,8-Octanedithiol)

3D-SDF for HMDB0040348 (1,8-Octanedithiol)

PDB for HMDB0040348 (1,8-Octanedithiol)

3D PDB for HMDB0040348 (1,8-Octanedithiol)

SMILES for HMDB0040348 (1,8-Octanedithiol)

INCHI for HMDB0040348 (1,8-Octanedithiol)

Structure for HMDB0040348 (1,8-Octanedithiol)

3D Structure for HMDB0040348 (1,8-Octanedithiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra