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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:43:37 UTC

Update Date

2022-03-07 02:56:29 UTC

HMDB ID

HMDB0040185

Secondary Accession Numbers

HMDB40185

Metabolite Identification

Common Name

3-Mercapto-2-butanol

Description

3-Mercapto-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). 3-Mercapto-2-butanol is a sulfurous tasting compound. Based on a literature review very few articles have been published on 3-Mercapto-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
2-Hydroxy-3-butanethiol	HMDB
2-mercapto-3-Butanol	HMDB
3-Hydroxy-2-butanethiol	HMDB
3-mercapto-2-Butanol, mixture OF isomers	HMDB
FEMA 3502	HMDB
3-Sulphanylbutan-2-ol	Generator

Chemical Formula

C₄H₁₀OS

Average Molecular Weight

106.187

Monoisotopic Molecular Weight

106.045235632

IUPAC Name

3-sulfanylbutan-2-ol

Traditional Name

3-sulfanylbutan-2-ol

CAS Registry Number

54812-86-1

SMILES

CC(O)C(C)S

InChI Identifier

InChI=1S/C4H10OS/c1-3(5)4(2)6/h3-6H,1-2H3

InChI Key

MJQWABQELVFQJL-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
Alkylthiol
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Sulfurous

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040185)
Cytoplasm (HMDB: HMDB0040185)

Source

Exogenous

Exogenous (HMDB: HMDB0040185)

Food

Food (HMDB: HMDB0040185)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040185)

Biological role

Nutrient (HMDB: HMDB0040185)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	162.00 to 163.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	31950 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.477 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.7 g/L	ALOGPS
logP	1.06	ALOGPS
logP	0.69	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	29.55 m³·mol⁻¹	ChemAxon
Polarizability	11.79 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]+	119.894	31661259
DarkChem	[M-H]-	115.692	31661259
DeepCCS	[M+H]+	126.193	30932474
DeepCCS	[M-H]-	124.107	30932474
DeepCCS	[M-2H]-	159.678	30932474
DeepCCS	[M+Na]+	134.411	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	123.2	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	135.1	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	145.1	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.	1.51 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4661 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	54.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1497.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	380.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	224.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.3 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	447.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	186.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	727.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	290.4 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	974.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.1 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	91.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-2-butanol	CC(O)C(C)S	1549.9	Standard polar	33892256
3-Mercapto-2-butanol	CC(O)C(C)S	860.0	Standard non polar	33892256
3-Mercapto-2-butanol	CC(O)C(C)S	867.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-2-butanol,1TMS,isomer #1	CC(S)C(C)O[Si](C)(C)C	985.6	Semi standard non polar	33892256
3-Mercapto-2-butanol,1TMS,isomer #2	CC(O)C(C)S[Si](C)(C)C	1054.0	Semi standard non polar	33892256
3-Mercapto-2-butanol,2TMS,isomer #1	CC(O[Si](C)(C)C)C(C)S[Si](C)(C)C	1200.1	Semi standard non polar	33892256
3-Mercapto-2-butanol,2TMS,isomer #1	CC(O[Si](C)(C)C)C(C)S[Si](C)(C)C	1174.3	Standard non polar	33892256
3-Mercapto-2-butanol,1TBDMS,isomer #1	CC(S)C(C)O[Si](C)(C)C(C)(C)C	1202.8	Semi standard non polar	33892256
3-Mercapto-2-butanol,1TBDMS,isomer #2	CC(O)C(C)S[Si](C)(C)C(C)(C)C	1290.8	Semi standard non polar	33892256
3-Mercapto-2-butanol,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(C)S[Si](C)(C)C(C)(C)C	1627.0	Semi standard non polar	33892256
3-Mercapto-2-butanol,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(C)S[Si](C)(C)C(C)(C)C	1635.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-9000000000-bee6da51dbbd05e2d142	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-2-butanol GC-MS (1 TMS) - 70eV, Positive	splash10-02p0-9600000000-aad246f5bd7e3b74d750	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-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 - 3-Mercapto-2-butanol 10V, Positive-QTOF	splash10-0a4r-9300000000-d6d1a2e047ac0c7e9093	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 20V, Positive-QTOF	splash10-0a4r-9500000000-b653d02b3bb37d9f7800	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 40V, Positive-QTOF	splash10-0a4i-9000000000-bedf748fd3a5509d4ad2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 10V, Negative-QTOF	splash10-0a4i-4900000000-e8652442a2e299a33560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 20V, Negative-QTOF	splash10-0abi-9400000000-68db8fd806d304be9219	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 40V, Negative-QTOF	splash10-00ei-9000000000-75fb51b0f7ea388a66c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 10V, Negative-QTOF	splash10-0a4i-0900000000-eb55bbeec12d01961039	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 20V, Negative-QTOF	splash10-001i-9100000000-70a166fe676538c8fa27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 40V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 10V, Positive-QTOF	splash10-052r-9000000000-1517693ee69807dbba10	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 20V, Positive-QTOF	splash10-0a4j-9000000000-7aee06e0c188462a7523	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-butanol 40V, Positive-QTOF	splash10-08fr-9000000000-804ed92b9f121a90f888	2021-09-22	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

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

FDB019897

KNApSAcK ID

Not Available

Chemspider ID

55924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62087

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1191151

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 3-Mercapto-2-butanol (HMDB0040185)

MOL for HMDB0040185 (3-Mercapto-2-butanol)

3D MOL for HMDB0040185 (3-Mercapto-2-butanol)

3D SDF for HMDB0040185 (3-Mercapto-2-butanol)

3D-SDF for HMDB0040185 (3-Mercapto-2-butanol)

PDB for HMDB0040185 (3-Mercapto-2-butanol)

3D PDB for HMDB0040185 (3-Mercapto-2-butanol)

SMILES for HMDB0040185 (3-Mercapto-2-butanol)

INCHI for HMDB0040185 (3-Mercapto-2-butanol)

Structure for HMDB0040185 (3-Mercapto-2-butanol)

3D Structure for HMDB0040185 (3-Mercapto-2-butanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra