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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:53 UTC

Update Date

2023-02-21 17:23:07 UTC

HMDB ID

HMDB0033129

Secondary Accession Numbers

HMDB33129

Metabolite Identification

Common Name

3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Description

3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one is an odorless tasting compound. Based on a literature review very few articles have been published on 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    4    6                                                       
CONECT    4    1    3   12                                                  
CONECT    5    2    7    9                                                  
CONECT    6    3    7   10                                                  
CONECT    7    5    6    8                                                  
CONECT    8    7   11   12                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dehydracetic acid	HMDB
Dehydroacetic acid	HMDB
Methylacetopyronone	HMDB
DHAS	MeSH, HMDB
Dehydroacetic acid, potassium ion (1-)	MeSH, HMDB
Dehydroacetic acid, sodium ion (1-)	MeSH, HMDB
Dehydroacetic acid, zinc ion (1-)	MeSH, HMDB
Dehydroacetic acid ion (1-)	MeSH, HMDB
DHA-S	MeSH, HMDB
Dehydroacetic acid, sodium monohydrate ion (1-)	MeSH, HMDB
Dihydroxyacetone sulfate	MeSH, HMDB
Sodium dehydroacetate	MeSH, HMDB
Dehydroacetate	Generator

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Traditional Name

3-acetyl-4-hydroxy-6-methylpyran-2-one

CAS Registry Number

771-03-9

SMILES

CC(=O)C1=C(O)C=C(C)OC1=O

InChI Identifier

InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,10H,1-2H3

InChI Key

PKLPQOJFHFGVBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyranone
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033129)
Cytoplasm (HMDB: HMDB0033129)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033129)

Source

Exogenous

Food

Food (HMDB: HMDB0033129)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033129)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	109 °C	Not Available
Boiling Point	352.00 to 353.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	817800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.221 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.12 g/L	ALOGPS
logP	0.08	ALOGPS
logP	0.47	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	6.49	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.43 m³·mol⁻¹	ChemAxon
Polarizability	15.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.767	31661259
DarkChem	[M-H]-	135.931	31661259
DeepCCS	[M+H]+	132.849	30932474
DeepCCS	[M-H]-	129.02	30932474
DeepCCS	[M-2H]-	166.733	30932474
DeepCCS	[M+Na]+	142.272	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	138.2	32859911
AllCCS	[M+Na]+	139.4	32859911
AllCCS	[M-H]-	132.1	32859911
AllCCS	[M+Na-2H]-	133.1	32859911
AllCCS	[M+HCOO]-	134.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one	CC(=O)C1=C(O)C=C(C)OC1=O	1920.8	Standard polar	33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one	CC(=O)C1=C(O)C=C(C)OC1=O	1568.2	Standard non polar	33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one	CC(=O)C1=C(O)C=C(C)OC1=O	1329.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,1TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C(C)OC1=O	1588.0	Semi standard non polar	33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,1TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C)OC1=O	1840.5	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 - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v03-5900000000-88feceb65a900415a7fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-9750000000-35bd9230699a5ce09dbc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 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-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-014i-0900000000-fe08202ce08585250c13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-014i-0900000000-bd5f45f8f94e766bd9d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-0pc9-4900000000-414640773faaabce2565	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-014i-0900000000-0087476b0935000afd8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-004i-2900000000-5c44a21e733f2784dd8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-001i-9500000000-dbca1de8be7e3b295f4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-014i-0900000000-647525daac9281f7e601	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-016r-2900000000-af544e3828cc82d85391	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-0006-9000000000-0b60e0eff1ec85de185c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-014i-0900000000-930f9ca2cc854ecca14e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-016r-1900000000-02682960868c1120ad26	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-05mx-9000000000-06c4c7a773034883d277	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+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

FDB011130

KNApSAcK ID

Not Available

Chemspider ID

10486535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54678494

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1529191

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-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (HMDB0033129)

MOL for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

3D MOL for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

3D SDF for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

3D-SDF for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

PDB for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

3D PDB for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

SMILES for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

INCHI for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

Structure for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

3D Structure for HMDB0033129 (3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra