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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:37:33 UTC

Update Date

2023-02-21 17:23:41 UTC

HMDB ID

HMDB0033851

Secondary Accession Numbers

HMDB33851

Metabolite Identification

Common Name

4,4-Dimethoxy-2-butanone

Description

4,4-Dimethoxy-2-butanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 4,4-Dimethoxy-2-butanone is an alcoholic, bitter, and ethereal tasting compound. Based on a literature review very few articles have been published on 4,4-Dimethoxy-2-butanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,1-Dimethoxy-3-butanone	HMDB
3-Ketobutyraldehyde dimethyl acetal	HMDB
3-Ketobutyraldehyde dimethylacetal	HMDB
3-Oxobutanal dimethyl acetal	HMDB
3-Oxobutanal, dimethyl acetal	HMDB
3-Oxobutyraldehyde 1-(dimethylacetal)	HMDB
3-Oxobutyraldehyde dimethyl acetal	HMDB
3-Oxobutyraldehyde dimethylacetal	HMDB
4,4-Dimethoxy-2-butanone, 9ci	HMDB
4,4-Dimethoxybutan-2-one	HMDB
4,4-Dimethoxybutanone	HMDB
Acetoacetaldehyde 1-(dimethyl acetal)	HMDB
Acetoacetaldehyde dimethyl acetal	HMDB
Acetoacetaldehyde, 1-(dimethyl acetal)	HMDB
Acetoacetaldehyde, 1-(dimethyl acetal) (6ci,7ci,8ci)	HMDB
Acetylacetaldehyddimethylacetal	HMDB
Acetylacetaldehyde dimethyl acetal	HMDB
Acetylacetaldehyde dimethylacetal	HMDB
beta -Oxobutyraldehyde dimethyl acetal	HMDB
beta-Oxobutyraldehyde dimethyl acetal	HMDB
BUTANAL,2-oxo,dimethyl acetal	HMDB
FEMA 3381	HMDB
Formylacetone dimethyl acetal	HMDB

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

4,4-dimethoxybutan-2-one

Traditional Name

2-butanone, 4,4-dimethoxy-

CAS Registry Number

5436-21-5

SMILES

COC(CC(C)=O)OC

InChI Identifier

InChI=1S/C6H12O3/c1-5(7)4-6(8-2)9-3/h6H,4H2,1-3H3

InChI Key

PJCCSZUMZMCWSX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Acetal
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0033851)

Exogenous

Food

Food (HMDB: HMDB0033851)

Exogenous (HMDB: HMDB0033851)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0033851)

Role

Biological role

Energy source (HMDB: HMDB0033851)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033851)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033851)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-83.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	178.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	-0.067 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	99.5 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.45	ChemAxon
logS	-0.12	ALOGPS
pKa (Strongest Acidic)	17.4	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.13 m³·mol⁻¹	ChemAxon
Polarizability	13.79 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]+	130.754	31661259
DarkChem	[M-H]-	125.81	31661259
DeepCCS	[M+H]+	122.787	30932474
DeepCCS	[M-H]-	119.622	30932474
DeepCCS	[M-2H]-	156.039	30932474
DeepCCS	[M+Na]+	131.344	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	132.5	32859911
AllCCS	[M+HCOO]-	135.7	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.	3.28 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8572 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1666.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	372.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.8 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	391.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	902.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	328.6 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	942.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.9 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	31.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,4-Dimethoxy-2-butanone	COC(CC(C)=O)OC	1717.0	Standard polar	33892256
4,4-Dimethoxy-2-butanone	COC(CC(C)=O)OC	878.4	Standard non polar	33892256
4,4-Dimethoxy-2-butanone	COC(CC(C)=O)OC	871.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,4-Dimethoxy-2-butanone,1TMS,isomer #1	COC(C=C(C)O[Si](C)(C)C)OC	1086.2	Semi standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TMS,isomer #1	COC(C=C(C)O[Si](C)(C)C)OC	977.4	Standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TMS,isomer #2	C=C(CC(OC)OC)O[Si](C)(C)C	1050.9	Semi standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TMS,isomer #2	C=C(CC(OC)OC)O[Si](C)(C)C	1031.6	Standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TBDMS,isomer #1	COC(C=C(C)O[Si](C)(C)C(C)(C)C)OC	1314.5	Semi standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TBDMS,isomer #1	COC(C=C(C)O[Si](C)(C)C(C)(C)C)OC	1200.5	Standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TBDMS,isomer #2	C=C(CC(OC)OC)O[Si](C)(C)C(C)(C)C	1265.2	Semi standard non polar	33892256
4,4-Dimethoxy-2-butanone,1TBDMS,isomer #2	C=C(CC(OC)OC)O[Si](C)(C)C(C)(C)C	1256.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4,4-Dimethoxy-2-butanone EI-B (Non-derivatized)	splash10-002f-9000000000-248141bca8e1165eafd7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4,4-Dimethoxy-2-butanone EI-B (Non-derivatized)	splash10-002f-9000000000-248141bca8e1165eafd7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4-Dimethoxy-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-03d32fe8b0479dd437bc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4-Dimethoxy-2-butanone 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 - 4,4-Dimethoxy-2-butanone 10V, Positive-QTOF	splash10-00lr-1900000000-a25ce560c731f065f4aa	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 20V, Positive-QTOF	splash10-0159-3900000000-c86186a65402372b8b0c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 40V, Positive-QTOF	splash10-00ku-9200000000-d61fd218fef43c121083	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 10V, Negative-QTOF	splash10-001i-1900000000-fff5a4751f6278585002	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 20V, Negative-QTOF	splash10-001i-6900000000-d69bc18fd61f22744bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 40V, Negative-QTOF	splash10-067r-9100000000-3b533425df88ee07e18f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 10V, Negative-QTOF	splash10-0a59-9300000000-39bf7fffdf2a02a56f77	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 20V, Negative-QTOF	splash10-052f-9000000000-f85c692b08566fecece7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 40V, Negative-QTOF	splash10-0a4i-9000000000-4e3dec55aee2ca5f97bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 10V, Positive-QTOF	splash10-0kal-9300000000-0e0795f2c6a5c02a493e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 20V, Positive-QTOF	splash10-000f-9000000000-bb205cf54bf3b17d6042	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4-Dimethoxy-2-butanone 40V, Positive-QTOF	splash10-0006-9000000000-f66065e0608b5b4ecedc	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB012031

KNApSAcK ID

Not Available

Chemspider ID

198921

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

228548

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036051

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 4,4-Dimethoxy-2-butanone (HMDB0033851)

MOL for HMDB0033851 (4,4-Dimethoxy-2-butanone)

3D MOL for HMDB0033851 (4,4-Dimethoxy-2-butanone)

3D SDF for HMDB0033851 (4,4-Dimethoxy-2-butanone)

3D-SDF for HMDB0033851 (4,4-Dimethoxy-2-butanone)

PDB for HMDB0033851 (4,4-Dimethoxy-2-butanone)

3D PDB for HMDB0033851 (4,4-Dimethoxy-2-butanone)

SMILES for HMDB0033851 (4,4-Dimethoxy-2-butanone)

INCHI for HMDB0033851 (4,4-Dimethoxy-2-butanone)

Structure for HMDB0033851 (4,4-Dimethoxy-2-butanone)

3D Structure for HMDB0033851 (4,4-Dimethoxy-2-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra