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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:09:58 UTC

Update Date

2023-02-21 17:28:44 UTC

HMDB ID

HMDB0041476

Secondary Accession Numbers

HMDB41476

Metabolite Identification

Common Name

4-(Methylthio)-2-butanol

Description

4-(Methylthio)-2-butanol belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). 4-(Methylthio)-2-butanol has been detected, but not quantified in, alcoholic beverages. This could make 4-(methylthio)-2-butanol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-(Methylthio)-2-butanol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(methylthio)-2-Butanol, 9ci	HMDB
4-(Methylsulphanyl)butan-2-ol	Generator

Chemical Formula

C₅H₁₂OS

Average Molecular Weight

120.213

Monoisotopic Molecular Weight

120.060885696

IUPAC Name

4-(methylsulfanyl)butan-2-ol

Traditional Name

4-(methylsulfanyl)butan-2-ol

CAS Registry Number

13296-23-6

SMILES

CSCCC(C)O

InChI Identifier

InChI=1S/C5H12OS/c1-5(6)3-4-7-2/h5-6H,3-4H2,1-2H3

InChI Key

BQFFCKMCUHRYIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Secondary alcohol
Dialkylthioether
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041476)
Cytoplasm (HMDB: HMDB0041476)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041476)

Source

Exogenous

Exogenous (HMDB: HMDB0041476)

Food

Food (HMDB: HMDB0041476)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041476)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18680 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.5 g/L	ALOGPS
logP	0.94	ALOGPS
logP	0.91	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	15.64	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.52 m³·mol⁻¹	ChemAxon
Polarizability	14.08 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]+	123.915	31661259
DarkChem	[M-H]-	118.961	31661259
DeepCCS	[M+H]+	131.27	30932474
DeepCCS	[M-H]-	129.374	30932474
DeepCCS	[M-2H]-	165.007	30932474
DeepCCS	[M+Na]+	139.51	30932474
AllCCS	[M+H]+	127.8	32859911
AllCCS	[M+H-H2O]+	123.7	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	141.4	32859911
AllCCS	[M+HCOO]-	145.8	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.	2.77 minutes	32390414
Predicted by Siyang on May 30, 2022	11.037 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	42.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1509.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	373.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	109.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	228.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	367.7 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	491.1 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	868.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	316.2 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	990.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	378.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.9 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	57.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(Methylthio)-2-butanol	CSCCC(C)O	1640.7	Standard polar	33892256
4-(Methylthio)-2-butanol	CSCCC(C)O	951.2	Standard non polar	33892256
4-(Methylthio)-2-butanol	CSCCC(C)O	1001.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(Methylthio)-2-butanol,1TMS,isomer #1	CSCCC(C)O[Si](C)(C)C	1101.5	Semi standard non polar	33892256
4-(Methylthio)-2-butanol,1TBDMS,isomer #1	CSCCC(C)O[Si](C)(C)C(C)(C)C	1332.0	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 - 4-(Methylthio)-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9100000000-8fcab4e8a6230fed2ce6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Methylthio)-2-butanol GC-MS (1 TMS) - 70eV, Positive	splash10-00vr-9600000000-c6a93b209ce59105aad5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Methylthio)-2-butanol 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 - 4-(Methylthio)-2-butanol 10V, Positive-QTOF	splash10-0udi-0900000000-fc8c8ad2be7bbf909576	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 20V, Positive-QTOF	splash10-0zfr-6900000000-9335796d3b06e74e9790	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 40V, Positive-QTOF	splash10-0a4i-9000000000-f721f4a42fe8a09794fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 10V, Negative-QTOF	splash10-014j-9800000000-246817429aa0bb4ddc9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 20V, Negative-QTOF	splash10-0002-9200000000-7db2a1a4b02012af72f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 40V, Negative-QTOF	splash10-0002-9000000000-34ef0753c9d8573c3036	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 10V, Negative-QTOF	splash10-014j-6900000000-987ad8022b02efcc5ec5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 10V, Positive-QTOF	splash10-0w29-8900000000-a3c7b7b06390df8f436c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 20V, Positive-QTOF	splash10-0bvi-9000000000-fdb72e46d7676d5663bd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylthio)-2-butanol 40V, Positive-QTOF	splash10-08fs-9000000000-0baf498e550bd925bf26	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB021437

KNApSAcK ID

Not Available

Chemspider ID

15996125

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12659797

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892781

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 4-(Methylthio)-2-butanol (HMDB0041476)

MOL for HMDB0041476 (4-(Methylthio)-2-butanol)

3D MOL for HMDB0041476 (4-(Methylthio)-2-butanol)

3D SDF for HMDB0041476 (4-(Methylthio)-2-butanol)

3D-SDF for HMDB0041476 (4-(Methylthio)-2-butanol)

PDB for HMDB0041476 (4-(Methylthio)-2-butanol)

3D PDB for HMDB0041476 (4-(Methylthio)-2-butanol)

SMILES for HMDB0041476 (4-(Methylthio)-2-butanol)

INCHI for HMDB0041476 (4-(Methylthio)-2-butanol)

Structure for HMDB0041476 (4-(Methylthio)-2-butanol)

3D Structure for HMDB0041476 (4-(Methylthio)-2-butanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra