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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:53 UTC

Update Date

2023-02-21 17:18:58 UTC

HMDB ID

HMDB0029660

Secondary Accession Numbers

HMDB29660

Metabolite Identification

Common Name

2',6'-Dihydroxyacetophenone

Description

2',6'-Dihydroxyacetophenone 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. Based on a literature review very few articles have been published on 2',6'-Dihydroxyacetophenone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,6-Dihydroxyacetophenone	MeSH
Dihydroxyacetophenone	MeSH
26-Dihydroxy acetophenone	ChEMBL, HMDB
2'6'-Dihydroxyacetophenone	ChEMBL, HMDB
26-Dihydroxyacetophenone	ChEMBL, HMDB
1-(2,6-Dihydroxyphenyl)-ethanone	HMDB
1-(2,6-Dihydroxyphenyl)ethanone	HMDB
1-(2,6-Dihydroxyphenyl)ethanone, 9ci	HMDB
2',6'-Dihydroxy-acetophenone	HMDB
2, 6-Dihydroxyacetophenone	HMDB
2-Acetyl-1,3-benzenediol	HMDB
2-Acetyl-1,3-dihydroxybenzene	HMDB
2-Acetyl-resorcinol	HMDB
2-Acetylresorcinol	HMDB
Acetophenone, 2',6'-dihydroxy- (8ci)	HMDB
Acetyl-2,6-dihydroxybenzene	HMDB
Ethanone, 1-(2,6-dihydroxyphenyl)- (9ci)	HMDB
gamma-Resacetophenone	HMDB
laquo gammaraquo -Resacetophenone	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(2,6-dihydroxyphenyl)ethan-1-one

Traditional Name

1-(2,6-dihydroxyphenyl)ethanone

CAS Registry Number

699-83-2

SMILES

CC(=O)C1=C(O)C=CC=C1O

InChI Identifier

InChI=1S/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3

InChI Key

YPTJKHVBDCRKNF-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
Acetophenone
Aryl alkyl ketone
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029660)
Cytoplasm (HMDB: HMDB0029660)

Source

Endogenous

Endogenous (HMDB: HMDB0029660)

Exogenous

Food

Food (HMDB: HMDB0029660)

Exogenous (HMDB: HMDB0029660)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029660)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 - 156 °C	Not Available
Boiling Point	262.77 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3269 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.922 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.84 g/L	ALOGPS
logP	1.26	ALOGPS
logP	2.22	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.42 m³·mol⁻¹	ChemAxon
Polarizability	14.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	133.298	31661259
DarkChem	[M-H]-	128.223	31661259
DeepCCS	[M+H]+	133.532	30932474
DeepCCS	[M-H]-	131.074	30932474
DeepCCS	[M-2H]-	166.958	30932474
DeepCCS	[M+Na]+	141.931	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.8	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	127.7	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	130.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',6'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC=C1O	1851.4	Standard polar	33892256
2',6'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC=C1O	1326.4	Standard non polar	33892256
2',6'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC=C1O	1260.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',6'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=C(O)C=CC=C1O[Si](C)(C)C	1436.3	Semi standard non polar	33892256
2',6'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=CC=C1O[Si](C)(C)C	1538.9	Semi standard non polar	33892256
2',6'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=C(O)C=CC=C1O[Si](C)(C)C(C)(C)C	1696.4	Semi standard non polar	33892256
2',6'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O[Si](C)(C)C(C)(C)C	2013.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2',6'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-2b6e748d6358fdcf057c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',6'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-2b6e748d6358fdcf057c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',6'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-5900000000-9a72100ff2abdd699021	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',6'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-7390000000-1c230be671a61b10bac6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',6'-Dihydroxyacetophenone 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'-Dihydroxyacetophenone ESI-TOF 20V, Negative-QTOF	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF 30V, Negative-QTOF	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF , Negative-QTOF	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF 10V, Negative-QTOF	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF 20V, Negative-QTOF	splash10-0pbi-0900000000-339591e82b6f9e9fd3af	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF 30V, Negative-QTOF	splash10-0a4r-0900000000-d7933852722676de249b	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF , Negative-QTOF	splash10-0udi-0900000000-afca75e5da74cd4bcb42	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone ESI-TOF 10V, Negative-QTOF	splash10-0udi-0900000000-bbc9d0fbc313d0295c5f	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone LC-ESI-TOF , negative-QTOF	splash10-0pbi-0900000000-339591e82b6f9e9fd3af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone LC-ESI-TOF , negative-QTOF	splash10-0a4r-0900000000-d7933852722676de249b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone LC-ESI-TOF , negative-QTOF	splash10-0udi-0900000000-bbc9d0fbc313d0295c5f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-bbc9d0fbc313d0295c5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 30V, Positive-QTOF	splash10-0a4r-0900000000-d7933852722676de249b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0pbi-0900000000-339591e82b6f9e9fd3af	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-d0bd719bf38331475fb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-779ce2168b7f4c84b4c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-000i-8900000000-7a081ec595bc24a11b28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-75e70d0a6447a92db7a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0pb9-0900000000-5e3331083120f85454e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0a4r-6900000000-ec459163541c38b65c4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-fe0c32c36077cbdf6cbc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0pb9-0900000000-8f236646508bea168933	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-014i-9100000000-c16f0fc4101d3af6c24b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-1900000000-eec78dbc37968f080384	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',6'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-000f-5900000000-22c3bd9a4f5a2991a4fe	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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+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

FDB000834

KNApSAcK ID

Not Available

Chemspider ID

62888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69687

PDB ID

Not Available

ChEBI ID

559127

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1157831

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'-Dihydroxyacetophenone (HMDB0029660)

MOL for HMDB0029660 (2',6'-Dihydroxyacetophenone)

3D MOL for HMDB0029660 (2',6'-Dihydroxyacetophenone)

3D SDF for HMDB0029660 (2',6'-Dihydroxyacetophenone)

3D-SDF for HMDB0029660 (2',6'-Dihydroxyacetophenone)

PDB for HMDB0029660 (2',6'-Dihydroxyacetophenone)

3D PDB for HMDB0029660 (2',6'-Dihydroxyacetophenone)

SMILES for HMDB0029660 (2',6'-Dihydroxyacetophenone)

INCHI for HMDB0029660 (2',6'-Dihydroxyacetophenone)

Structure for HMDB0029660 (2',6'-Dihydroxyacetophenone)

3D Structure for HMDB0029660 (2',6'-Dihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra