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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:56:33 UTC

Update Date

2023-02-21 17:28:36 UTC

HMDB ID

HMDB0041270

Secondary Accession Numbers

HMDB41270

Metabolite Identification

Common Name

2',4'-Dihydroxy-6'-methoxyacetophenone

Description

2',4'-Dihydroxy-6'-methoxyacetophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2',4'-Dihydroxy-6'-methoxyacetophenone has been detected, but not quantified in, herbs and spices. This could make 2',4'-dihydroxy-6'-methoxyacetophenone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2',4'-Dihydroxy-6'-methoxyacetophenone.

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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   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       0.000   1.540   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    1    9   10                                                  
CONECT    6    3    4   11                                                  
CONECT    7    3    9   12                                                  
CONECT    8    4    9   13                                                  
CONECT    9    5    7    8                                                  
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

1-(2,4-dihydroxy-6-methoxyphenyl)ethan-1-one

Traditional Name

1-(2,4-dihydroxy-6-methoxyphenyl)ethanone

CAS Registry Number

3602-54-8

SMILES

COC1=CC(O)=CC(O)=C1C(C)=O

InChI Identifier

InChI=1S/C9H10O4/c1-5(10)9-7(12)3-6(11)4-8(9)13-2/h3-4,11-12H,1-2H3

InChI Key

IETZAWFZIAOWQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyphenol
Acetophenone
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Resorcinol
Aryl alkyl ketone
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ether
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041270)
Cytoplasm (HMDB: HMDB0041270)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041270)

Source

Exogenous

Food

Food (HMDB: HMDB0041270)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041270)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041270)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 - 199 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9301 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.92 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.42	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	17.71 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]+	142.4	31661259
DarkChem	[M-H]-	139.052	31661259
DeepCCS	[M+H]+	141.918	30932474
DeepCCS	[M-H]-	139.214	30932474
DeepCCS	[M-2H]-	175.088	30932474
DeepCCS	[M+Na]+	150.626	30932474
AllCCS	[M+H]+	138.7	32859911
AllCCS	[M+H-H2O]+	134.4	32859911
AllCCS	[M+NH4]+	142.7	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	138.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',4'-Dihydroxy-6'-methoxyacetophenone	COC1=CC(O)=CC(O)=C1C(C)=O	2515.6	Standard polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone	COC1=CC(O)=CC(O)=C1C(C)=O	1610.8	Standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone	COC1=CC(O)=CC(O)=C1C(C)=O	1791.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',4'-Dihydroxy-6'-methoxyacetophenone,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(O)=C1C(C)=O	1667.6	Semi standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone,1TMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C)=C1C(C)=O	1674.2	Semi standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(C)=O	1750.6	Semi standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(C)=O	1938.3	Semi standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone,1TBDMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(C)=O	1945.2	Semi standard non polar	33892256
2',4'-Dihydroxy-6'-methoxyacetophenone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(C)=O	2228.3	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 - 2',4'-Dihydroxy-6'-methoxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2900000000-32a00c3d6fa73f62099c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-03di-8498000000-2b672c02bfe539209975	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 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 - 2',4'-Dihydroxy-6'-methoxyacetophenone 10V, Positive-QTOF	splash10-001i-0900000000-23b2ef224ff433e50a49	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 20V, Positive-QTOF	splash10-001i-0900000000-747de91ee80c580a780c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 40V, Positive-QTOF	splash10-014s-8900000000-b97e7ecac513ff388678	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 10V, Negative-QTOF	splash10-001i-0900000000-e0e679fe475c7a57dd27	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 20V, Negative-QTOF	splash10-0019-0900000000-7c9a9858ca440374d266	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 40V, Negative-QTOF	splash10-0a5m-9800000000-55e4fcf2af8e7bb8bee0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 10V, Positive-QTOF	splash10-001i-0900000000-f1422d8a8771acc70b85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 20V, Positive-QTOF	splash10-00lr-1900000000-04f0989ed56329ba93f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 40V, Positive-QTOF	splash10-0frx-9100000000-0f6a8fcebf33356c9a98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 10V, Negative-QTOF	splash10-001i-0900000000-f920cbe124bfe3593c3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 20V, Negative-QTOF	splash10-001r-0900000000-d6c83c4dbdd644e6149c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxy-6'-methoxyacetophenone 40V, Negative-QTOF	splash10-05mo-9200000000-e01d17976c0cec3a9e19	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

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

FDB021182

KNApSAcK ID

Not Available

Chemspider ID

9140356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10965145

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1890981

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 2',4'-Dihydroxy-6'-methoxyacetophenone (HMDB0041270)

MOL for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

3D MOL for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

3D SDF for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

3D-SDF for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

PDB for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

3D PDB for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

SMILES for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

INCHI for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

Structure for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

3D Structure for HMDB0041270 (2',4'-Dihydroxy-6'-methoxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra