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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:45 UTC

Update Date

2023-02-21 17:20:42 UTC

HMDB ID

HMDB0031511

Secondary Accession Numbers

HMDB31511

Metabolite Identification

Common Name

Diacetone alcohol

Description

Diacetone alcohol belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Thus, diacetone alcohol is considered to be an oxygenated hydrocarbon. Diacetone alcohol is found, on average, in the highest concentration within milk (cow). Diacetone alcohol has also been detected, but not quantified in, several different foods, such as fruits, mung beans (Vigna radiata), papayas (Carica papaya), and soy beans (Glycine max). This could make diacetone alcohol a potential biomarker for the consumption of these foods. Diacetone alcohol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Diacetone alcohol.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-2-pentanol-4-one	ChEBI
4-Hydroxy-2-keto-4-methylpentane	ChEBI
4-Hydroxy-4-methyl-2-pentanone	ChEBI
4-Hydroxy-4-methylpentan-2-one	ChEBI
Acetonyldimethylcarbinol	ChEBI
Diacetonalkohol	ChEBI
Diacetone-alcool	ChEBI
Diacetonyl alcohol	ChEBI
Dimethyl acetonyl carbinol	ChEBI
(CH3)2C(OH)CH2C(O)CH3	HMDB
2-Hydroxy-2-methyl-4-pentanone	HMDB
2-Methyl-3-pentanol-4-one	HMDB
4-Hydroxy-4-methyl pentan-2-one	HMDB
4-Hydroxy-4-methyl-pentan-2-ON	HMDB
4-Hydroxy-4-methylpentanone	HMDB
4-Hydroxy-4-methylpentanone-2	HMDB
4-Idrossi-4-metil-pentan-2-one	HMDB
4-Methyl-2-pentanon-4-ol	HMDB
4-Methyl-4-hydroxy-2-pentanone	HMDB
Diacetonalcohol	HMDB
Diacetonalcool	HMDB
Diacetone	HMDB
Diacetonealcool	HMDB
Diketone alcohol	HMDB
Hydroxy-4-methyl-2-pentanone	HMDB
Pyranton	HMDB
Pyranton a	HMDB
Pyraton	HMDB
Tyranton	HMDB
Diacetone alcohol	MeSH

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

4-hydroxy-4-methylpentan-2-one

Traditional Name

diacetone alcohol

CAS Registry Number

123-42-2

SMILES

CC(=O)CC(C)(C)O

InChI Identifier

InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

InChI Key

SWXVUIWOUIDPGS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta-hydroxy ketones

Alternative Parents

Substituents

Beta-hydroxy ketone
Tertiary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-hydroxy ketone (CHEBI:55381 )
Oxygenated hydrocarbons (LMFA12000071 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031511)
Cytoplasm (HMDB: HMDB0031511)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031511)

Source

Endogenous

Endogenous (HMDB: HMDB0031511)

Plant

Plant (HMDB: HMDB0031511)

Exogenous

Food

Food (HMDB: HMDB0031511)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Soy

Soy bean (FooDB: FOOD00085)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Tropical fruit

Papaya (FooDB: FOOD00041)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-44 °C	Not Available
Boiling Point	164.00 to 166.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL at 25 °C	Not Available
LogP	0.026 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	145 g/L	ALOGPS
logP	0.04	ALOGPS
logP	0.22	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	-2.7	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	31.65 m³·mol⁻¹	ChemAxon
Polarizability	12.76 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]+	125.479	31661259
DarkChem	[M-H]-	120.092	31661259
DeepCCS	[M+H]+	130.953	30932474
DeepCCS	[M-H]-	128.468	30932474
DeepCCS	[M-2H]-	164.81	30932474
DeepCCS	[M+Na]+	139.931	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	122.4	32859911
AllCCS	[M+NH4]+	130.5	32859911
AllCCS	[M+Na]+	131.7	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	135.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diacetone alcohol	CC(=O)CC(C)(C)O	1322.1	Standard polar	33892256
Diacetone alcohol	CC(=O)CC(C)(C)O	823.4	Standard non polar	33892256
Diacetone alcohol	CC(=O)CC(C)(C)O	857.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diacetone alcohol,1TMS,isomer #1	CC(=O)CC(C)(C)O[Si](C)(C)C	1036.9	Semi standard non polar	33892256
Diacetone alcohol,1TMS,isomer #2	CC(=CC(C)(C)O)O[Si](C)(C)C	1052.9	Semi standard non polar	33892256
Diacetone alcohol,1TMS,isomer #3	C=C(CC(C)(C)O)O[Si](C)(C)C	1045.8	Semi standard non polar	33892256
Diacetone alcohol,2TMS,isomer #1	CC(=CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1188.8	Semi standard non polar	33892256
Diacetone alcohol,2TMS,isomer #1	CC(=CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1146.3	Standard non polar	33892256
Diacetone alcohol,2TMS,isomer #2	C=C(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1197.4	Semi standard non polar	33892256
Diacetone alcohol,2TMS,isomer #2	C=C(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1198.4	Standard non polar	33892256
Diacetone alcohol,1TBDMS,isomer #1	CC(=O)CC(C)(C)O[Si](C)(C)C(C)(C)C	1264.8	Semi standard non polar	33892256
Diacetone alcohol,1TBDMS,isomer #2	CC(=CC(C)(C)O)O[Si](C)(C)C(C)(C)C	1269.9	Semi standard non polar	33892256
Diacetone alcohol,1TBDMS,isomer #3	C=C(CC(C)(C)O)O[Si](C)(C)C(C)(C)C	1253.9	Semi standard non polar	33892256
Diacetone alcohol,2TBDMS,isomer #1	CC(=CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1626.1	Semi standard non polar	33892256
Diacetone alcohol,2TBDMS,isomer #1	CC(=CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1617.8	Standard non polar	33892256
Diacetone alcohol,2TBDMS,isomer #2	C=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1632.7	Semi standard non polar	33892256
Diacetone alcohol,2TBDMS,isomer #2	C=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1642.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diacetone alcohol EI-B (Non-derivatized)	splash10-052f-9000000000-8448b11a23b1992dae6d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diacetone alcohol EI-B (Non-derivatized)	splash10-052f-9000000000-8448b11a23b1992dae6d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetone alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-d76ed4086dd090eb3564	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetone alcohol GC-MS (1 TMS) - 70eV, Positive	splash10-008c-9800000000-7f63674d7679f4e1ffdf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetone alcohol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetone alcohol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-3c88eab79df5c6518f02	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QTOF 35V, positive-QTOF	splash10-0002-9000000000-572e128698f79d45b0ee	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QFT , negative-QTOF	splash10-014i-1900000000-ee905ffae28bda8d8940	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diacetone alcohol 35V, Positive-QTOF	splash10-0002-9000000000-ce506b6d6b03fb57f31b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Positive-QTOF	splash10-0002-9200000000-28461077d208c6f1dcdc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Positive-QTOF	splash10-000t-9100000000-7a7d9778efaa6f572988	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Positive-QTOF	splash10-001i-9000000000-73e251e1e66b5c21ea3e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Negative-QTOF	splash10-014i-4900000000-5c12de142cf98d10473d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Negative-QTOF	splash10-014j-9800000000-99f2184179878c0cef4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Negative-QTOF	splash10-0002-9000000000-357cee4d7e761ae81403	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Negative-QTOF	splash10-014j-5900000000-d8f659fff4ba77520c79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Negative-QTOF	splash10-0a4j-9000000000-54862b15a43515a383ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Negative-QTOF	splash10-0a4i-9000000000-8218e01622fc7846c262	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Positive-QTOF	splash10-0535-9000000000-b03f6065de8ca3b84c54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Positive-QTOF	splash10-0a5c-9000000000-44d30b07046cd79b826f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Positive-QTOF	splash10-0006-9000000000-de6bdbea5fe400146c1f	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

FDB008104

KNApSAcK ID

C00052715

Chemspider ID

13838151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diacetone_alcohol

METLIN ID

Not Available

PubChem Compound

31256

PDB ID

Not Available

ChEBI ID

55381

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1203631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Diacetone alcohol (HMDB0031511)

MOL for HMDB0031511 (Diacetone alcohol)

3D MOL for HMDB0031511 (Diacetone alcohol)

3D SDF for HMDB0031511 (Diacetone alcohol)

3D-SDF for HMDB0031511 (Diacetone alcohol)

PDB for HMDB0031511 (Diacetone alcohol)

3D PDB for HMDB0031511 (Diacetone alcohol)

SMILES for HMDB0031511 (Diacetone alcohol)

INCHI for HMDB0031511 (Diacetone alcohol)

Structure for HMDB0031511 (Diacetone alcohol)

3D Structure for HMDB0031511 (Diacetone alcohol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra