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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:10:58 UTC

Update Date

2023-02-21 17:28:45 UTC

HMDB ID

HMDB0041492

Secondary Accession Numbers

HMDB41492

Metabolite Identification

Common Name

1,2-Butanedithiol

Description

1,2-Butanedithiol belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. 1,2-Butanedithiol is a meat, roasted, and sulfur tasting compound. Based on a literature review very few articles have been published on 1,2-Butanedithiol.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dimercaptobutane	HMDB
1,2-Dithiolbutane	HMDB
1-Ethyl-1,2-ethanedithiol	HMDB
FEMA 3528	HMDB

Chemical Formula

C₄H₁₀S₂

Average Molecular Weight

122.24

Monoisotopic Molecular Weight

122.02239267

IUPAC Name

butane-1,2-dithiol

Traditional Name

butane-1,2-dithiol

CAS Registry Number

16128-68-0

SMILES

CCC(S)CS

InChI Identifier

InChI=1S/C4H10S2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3

InChI Key

LFTMJBWNOFFSRW-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

Extracellular (HMDB: HMDB0041492)
Cytoplasm (HMDB: HMDB0041492)

Source

Exogenous

Exogenous (HMDB: HMDB0041492)

Food

Food (HMDB: HMDB0041492)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0041492)

Biological role

Nutrient (HMDB: HMDB0041492)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	77.00 °C. @ 28.00 mm Hg	The Good Scents Company Information System
Water Solubility	1524 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.443 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	1.77	ALOGPS
logP	1.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.83 m³·mol⁻¹	ChemAxon
Polarizability	13.9 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]+	124.56	31661259
DarkChem	[M-H]-	118.925	31661259
DeepCCS	[M+H]+	130.92	30932474
DeepCCS	[M-H]-	128.878	30932474
DeepCCS	[M-2H]-	164.423	30932474
DeepCCS	[M+Na]+	139.082	30932474
AllCCS	[M+H]+	128.1	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	132.0	32859911
AllCCS	[M+Na]+	133.1	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	147.0	32859911
AllCCS	[M+HCOO]-	152.2	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.	2.57 minutes	32390414
Predicted by Siyang on May 30, 2022	18.2667 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	137.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2853.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	747.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	268.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	529.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	694.2 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	861.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1311.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1391.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	437.3 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	1612.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	544.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1009.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	707.4 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	239.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Butanedithiol	CCC(S)CS	1381.9	Standard polar	33892256
1,2-Butanedithiol	CCC(S)CS	950.5	Standard non polar	33892256
1,2-Butanedithiol	CCC(S)CS	978.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Butanedithiol,1TMS,isomer #1	CCC(CS)S[Si](C)(C)C	1207.7	Semi standard non polar	33892256
1,2-Butanedithiol,1TMS,isomer #1	CCC(CS)S[Si](C)(C)C	1143.0	Standard non polar	33892256
1,2-Butanedithiol,1TMS,isomer #2	CCC(S)CS[Si](C)(C)C	1247.6	Semi standard non polar	33892256
1,2-Butanedithiol,1TMS,isomer #2	CCC(S)CS[Si](C)(C)C	1147.9	Standard non polar	33892256
1,2-Butanedithiol,2TMS,isomer #1	CCC(CS[Si](C)(C)C)S[Si](C)(C)C	1354.7	Semi standard non polar	33892256
1,2-Butanedithiol,2TMS,isomer #1	CCC(CS[Si](C)(C)C)S[Si](C)(C)C	1369.6	Standard non polar	33892256
1,2-Butanedithiol,1TBDMS,isomer #1	CCC(CS)S[Si](C)(C)C(C)(C)C	1433.9	Semi standard non polar	33892256
1,2-Butanedithiol,1TBDMS,isomer #1	CCC(CS)S[Si](C)(C)C(C)(C)C	1391.7	Standard non polar	33892256
1,2-Butanedithiol,1TBDMS,isomer #2	CCC(S)CS[Si](C)(C)C(C)(C)C	1454.8	Semi standard non polar	33892256
1,2-Butanedithiol,1TBDMS,isomer #2	CCC(S)CS[Si](C)(C)C(C)(C)C	1390.7	Standard non polar	33892256
1,2-Butanedithiol,2TBDMS,isomer #1	CCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1852.4	Semi standard non polar	33892256
1,2-Butanedithiol,2TBDMS,isomer #1	CCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1818.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Butanedithiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0553-9000000000-f5cc7deeb59abc3975df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Butanedithiol 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 - 1,2-Butanedithiol 10V, Positive-QTOF	splash10-00dr-8900000000-0f12797b42cf4087e7d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 20V, Positive-QTOF	splash10-00dr-9700000000-2c63392d9080dc4d8f59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 40V, Positive-QTOF	splash10-0a4i-9000000000-07d321f29aa1171a59ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 10V, Negative-QTOF	splash10-00ei-9300000000-9143def3224ea339b11b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 20V, Negative-QTOF	splash10-0080-9200000000-e431cebd947dafbadc41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 40V, Negative-QTOF	splash10-001l-9000000000-71ff6d736dfb5251c69b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 10V, Positive-QTOF	splash10-0079-9300000000-eba7e0bc4365bcfb56ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 20V, Positive-QTOF	splash10-0a4i-9000000000-a2690bb536e5497971e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 40V, Positive-QTOF	splash10-0a4i-9000000000-ff2ad8adca66259789a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 10V, Negative-QTOF	splash10-00di-0900000000-c6c90ee53e3ecbfbad51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 20V, Negative-QTOF	splash10-00xr-9600000000-91603aded7b20cff0a94	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Butanedithiol 40V, Negative-QTOF	splash10-00di-9100000000-431485c89d4e08b111fa	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]-)	2023-02-04	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

Cytoplasm
Extracellular

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

FDB021462

KNApSAcK ID

Not Available

Chemspider ID

55704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61829

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036711

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 1,2-Butanedithiol (HMDB0041492)

MOL for HMDB0041492 (1,2-Butanedithiol)

3D MOL for HMDB0041492 (1,2-Butanedithiol)

3D SDF for HMDB0041492 (1,2-Butanedithiol)

3D-SDF for HMDB0041492 (1,2-Butanedithiol)

PDB for HMDB0041492 (1,2-Butanedithiol)

3D PDB for HMDB0041492 (1,2-Butanedithiol)

SMILES for HMDB0041492 (1,2-Butanedithiol)

INCHI for HMDB0041492 (1,2-Butanedithiol)

Structure for HMDB0041492 (1,2-Butanedithiol)

3D Structure for HMDB0041492 (1,2-Butanedithiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra