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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:46 UTC

Update Date

2023-02-21 17:18:56 UTC

HMDB ID

HMDB0029646

Secondary Accession Numbers

HMDB29646

Metabolite Identification

Common Name

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

Description

2',6'-Dihydroxy-4'-methoxyacetophenone, also known as 4-O-methylphloracetophenone, 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',6'-Dihydroxy-4'-methoxyacetophenone has been detected, but not quantified in, a few different foods, such as european plums (Prunus domestica), fruits, and sweet oranges (Citrus sinensis). This could make 2',6'-dihydroxy-4'-methoxyacetophenone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2',6'-Dihydroxy-4'-methoxyacetophenone.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.668   1.539   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.333   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.333  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.001  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.333  -0.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.333   0.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   1.541   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001   3.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.333   3.851   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.668   1.541   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.333   3.849   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.001  -3.079   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.333  -3.851   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    4   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-O-Methylphloracetophenone	Kegg
1-(2,6-Dihydroxy-4-methoxyphenyl)ethanone	HMDB
2,6-Dihydroxy-4-methoxyacetophenone	HMDB
Acetophenone, 2',6'-dihydroxy-4'-methoxy- (8ci)	HMDB
Ethanone, 1-(2,6-dihydroxy-4-methoxyphenyl)- (9ci)	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

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

Traditional Name

phloretin

CAS Registry Number

7507-89-3

SMILES

COC1=CC(O)=C(C(C)=O)C(O)=C1

InChI Identifier

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

InChI Key

GKSGTWUNURZTKD-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

acetophenones (CHEBI:28758 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029646)
Cytoplasm (HMDB: HMDB0029646)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029646)

Source

Endogenous

Endogenous (HMDB: HMDB0029646)

Plant

Plant (HMDB: HMDB0029646)

Exogenous

Food

Food (HMDB: HMDB0029646)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Drupe

European plum (FooDB: FOOD00147)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029646)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 142 °C	Not Available
Boiling Point	256.00 to 257.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2018 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.681 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	130.532	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001347

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.52 g/L	ALOGPS
logP	1.31	ALOGPS
logP	2.07	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.9	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	17.76 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]+	141.443	31661259
DarkChem	[M-H]-	141.782	31661259
DeepCCS	[M+H]+	139.333	30932474
DeepCCS	[M-H]-	136.795	30932474
DeepCCS	[M-2H]-	172.546	30932474
DeepCCS	[M+Na]+	148.085	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',6'-Dihydroxy-4'-methoxyacetophenone	COC1=CC(O)=C(C(C)=O)C(O)=C1	2507.3	Standard polar	33892256
2',6'-Dihydroxy-4'-methoxyacetophenone	COC1=CC(O)=C(C(C)=O)C(O)=C1	1572.9	Standard non polar	33892256
2',6'-Dihydroxy-4'-methoxyacetophenone	COC1=CC(O)=C(C(C)=O)C(O)=C1	1530.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',6'-Dihydroxy-4'-methoxyacetophenone,1TMS,isomer #1	COC1=CC(O)=C(C(C)=O)C(O[Si](C)(C)C)=C1	1668.3	Semi standard non polar	33892256
2',6'-Dihydroxy-4'-methoxyacetophenone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(C)=O)C(O[Si](C)(C)C)=C1	1747.6	Semi standard non polar	33892256
2',6'-Dihydroxy-4'-methoxyacetophenone,1TBDMS,isomer #1	COC1=CC(O)=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C1	1929.6	Semi standard non polar	33892256
2',6'-Dihydroxy-4'-methoxyacetophenone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C1	2208.4	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',6'-Dihydroxy-4'-methoxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1900000000-93889e5f20bb76b63fe8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-03k9-6769000000-9b0937634e48a577b6cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',6'-Dihydroxy-4'-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-4aaed325e55714a9cdae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-005a87e74e24dbd51f08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone Linear Ion Trap , positive-QTOF	splash10-0w29-0900000000-a1774d93f68427464dea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone Linear Ion Trap , positive-QTOF	splash10-0w29-0900000000-352750643de3c4eb9e08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 40V, Negative-QTOF	splash10-00dr-0900000000-a8047f33bb87d7ecba8b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 20V, Negative-QTOF	splash10-014i-0900000000-e008f31b1fc7daa050fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 10V, Negative-QTOF	splash10-00lr-0900000000-9e25b3f768d109522410	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 10V, Positive-QTOF	splash10-001i-0900000000-1a0ea4c444fec9f7edea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 20V, Positive-QTOF	splash10-001i-0900000000-7f7f0d9823e4effac33a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 40V, Positive-QTOF	splash10-00ku-2900000000-a6cac3d2c99cb5b54a39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 10V, Negative-QTOF	splash10-001i-0900000000-3bd6bf38aadcc609ff91	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 20V, Negative-QTOF	splash10-0019-0900000000-f5a04e4ce8eaf540ed78	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 40V, Negative-QTOF	splash10-052r-4900000000-396008c66101dba6a06a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 10V, Positive-QTOF	splash10-001i-0900000000-3e9846d5002daf16da8b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 20V, Positive-QTOF	splash10-014r-0900000000-a65bba64b1ba4e7dd1b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 40V, Positive-QTOF	splash10-00l6-9600000000-3a77fdcb7abac928ec57	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 10V, Negative-QTOF	splash10-001i-0900000000-49a059652c5c432bc06e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 20V, Negative-QTOF	splash10-001r-0900000000-3b2d046c574739f1801c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxy-4'-methoxyacetophenone 40V, Negative-QTOF	splash10-066r-9000000000-2267757a7334b76b9ccc	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24135

PDB ID

Not Available

ChEBI ID

562351

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1469261

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',6'-Dihydroxy-4'-methoxyacetophenone (HMDB0029646)

MOL for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

3D MOL for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

3D SDF for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

3D-SDF for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

PDB for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

3D PDB for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

SMILES for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

INCHI for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

Structure for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

3D Structure for HMDB0029646 (2',6'-Dihydroxy-4'-methoxyacetophenone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra