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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:47 UTC

Update Date

2023-02-21 17:20:44 UTC

HMDB ID

HMDB0031516

Secondary Accession Numbers

HMDB31516

Metabolite Identification

Common Name

3-Hydroxy-2-pentanone

Description

3-Hydroxy-2-pentanone belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thus, 3-hydroxy-2-pentanone is considered to be an oxygenated hydrocarbon. 3-Hydroxy-2-pentanone is a herbal and truffle tasting compound. 3-Hydroxy-2-pentanone is found, on average, in the highest concentration within beer. 3-Hydroxy-2-pentanone has also been detected, but not quantified in, asparagus (Asparagus officinalis). This could make 3-hydroxy-2-pentanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxy-2-pentanone.

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-oxo-3-Pentanol	HMDB
Acetylethylcarbinol	HMDB, MeSH
FEMA 3550	HMDB
3-Hydroxy-2-pentanone	MeSH

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

3-hydroxypentan-2-one

Traditional Name

3-hydroxypentan-2-one

CAS Registry Number

3142-66-3

SMILES

CCC(O)C(C)=O

InChI Identifier

InChI=1S/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3

InChI Key

HDKKRASBPHFULQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000022 )

Ontology

Not Available

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

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	105.00 to 107.00 °C. @ 50.00 mm Hg	The Good Scents Company Information System
Water Solubility	290700 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.211 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	283 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	0.38	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.91 m³·mol⁻¹	ChemAxon
Polarizability	11.03 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]+	121.037	31661259
DarkChem	[M-H]-	117.216	31661259
DeepCCS	[M+H]+	126.732	30932474
DeepCCS	[M-H]-	124.837	30932474
DeepCCS	[M-2H]-	160.536	30932474
DeepCCS	[M+Na]+	134.99	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	125.7	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-pentanone	CCC(O)C(C)=O	1294.3	Standard polar	33892256
3-Hydroxy-2-pentanone	CCC(O)C(C)=O	774.9	Standard non polar	33892256
3-Hydroxy-2-pentanone	CCC(O)C(C)=O	814.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-pentanone,1TMS,isomer #1	CCC(O[Si](C)(C)C)C(C)=O	965.4	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,1TMS,isomer #2	CCC(O)=C(C)O[Si](C)(C)C	1071.1	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,1TMS,isomer #3	C=C(O[Si](C)(C)C)C(O)CC	963.7	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TMS,isomer #1	CCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1192.8	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TMS,isomer #1	CCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1165.8	Standard non polar	33892256
3-Hydroxy-2-pentanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC)O[Si](C)(C)C	1118.4	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC)O[Si](C)(C)C	1115.1	Standard non polar	33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(C)=O	1190.8	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #2	CCC(O)=C(C)O[Si](C)(C)C(C)(C)C	1300.7	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(O)CC	1179.6	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1631.8	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1586.0	Standard non polar	33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C	1529.6	Semi standard non polar	33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C	1558.5	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-Hydroxy-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-08027296f0a19b418096	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-pentanone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9300000000-9793ae3a0b4ddfd1a1bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-pentanone 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-Hydroxy-2-pentanone 10V, Positive-QTOF	splash10-0udr-8900000000-fc4f2e76ee03f2fc544e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Positive-QTOF	splash10-0f79-9300000000-238db97e31076c69deff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Positive-QTOF	splash10-05mx-9000000000-855a711689fd0df6f943	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Negative-QTOF	splash10-0udi-2900000000-90004bd938f6ba2db603	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Negative-QTOF	splash10-0pb9-9300000000-bbce80bdc4443df17ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Negative-QTOF	splash10-0abc-9000000000-fbdf3bdb47ac16ffd5b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Positive-QTOF	splash10-0006-9000000000-54a3eb88039ed7669fac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Positive-QTOF	splash10-0006-9000000000-9d059a8148178f54694d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Positive-QTOF	splash10-0006-9000000000-3560c1d8216f72208cc8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Negative-QTOF	splash10-0udi-0900000000-4c159e60dacc58e6ba98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Negative-QTOF	splash10-0536-9000000000-cc8ee3e9af5120834aef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Negative-QTOF	splash10-0a4l-9000000000-c5ff37f832fb73100289	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008110

KNApSAcK ID

Not Available

Chemspider ID

56264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62484

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036801

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-Hydroxy-2-pentanone (HMDB0031516)

MOL for HMDB0031516 (3-Hydroxy-2-pentanone)

3D MOL for HMDB0031516 (3-Hydroxy-2-pentanone)

3D SDF for HMDB0031516 (3-Hydroxy-2-pentanone)

3D-SDF for HMDB0031516 (3-Hydroxy-2-pentanone)

PDB for HMDB0031516 (3-Hydroxy-2-pentanone)

3D PDB for HMDB0031516 (3-Hydroxy-2-pentanone)

SMILES for HMDB0031516 (3-Hydroxy-2-pentanone)

INCHI for HMDB0031516 (3-Hydroxy-2-pentanone)

Structure for HMDB0031516 (3-Hydroxy-2-pentanone)

3D Structure for HMDB0031516 (3-Hydroxy-2-pentanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra