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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:27:40 UTC

Update Date

2023-02-21 17:26:23 UTC

HMDB ID

HMDB0038179

Secondary Accession Numbers

HMDB38179

Metabolite Identification

Common Name

3-(2-Hydroxy-4-methylphenyl)-2-butanone

Description

3-(2-Hydroxy-4-methylphenyl)-2-butanone belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a small amount of articles have been published on 3-(2-Hydroxy-4-methylphenyl)-2-butanone.

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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    7   11                                                       
CONECT    7    1    4    6                                                  
CONECT    8    2    9   10                                                  
CONECT    9    3    8   12                                                  
CONECT   10    5    8   11                                                  
CONECT   11    6   10   13                                                  
CONECT   12    9                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0038179
HETATM    1  C1  UNL     1      -2.380  -1.285  -0.983  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.435   0.121  -0.568  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.115   0.883  -1.251  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.714   0.682   0.633  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.076   2.156   0.661  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.285   0.458   0.426  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.469   1.547  -0.030  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.826   1.442  -0.280  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.470   0.240  -0.080  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.927   0.140  -0.353  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.744  -0.837   0.368  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.385  -0.716   0.614  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.316  -1.809   1.065  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.396  -1.577  -1.418  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.113  -1.459  -1.829  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.690  -2.022  -0.224  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.129   0.219   1.527  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.446   2.719   1.380  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.111   2.207   1.069  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.120   2.600  -0.342  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.018   2.510  -0.203  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.421   2.272  -0.632  1.00  0.00           H  
HETATM   23  H10 UNL     1       4.119   0.827  -1.218  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.174  -0.914  -0.630  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.510   0.495   0.519  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.199  -1.798   0.540  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.064  -2.717   1.239  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5    6   17
CONECT    5   18   19   20
CONECT    6    7    7   12
CONECT    7    8   21
CONECT    8    9    9   22
CONECT    9   10   11
CONECT   10   23   24   25
CONECT   11   12   12   26
CONECT   12   13
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

3-(2-hydroxy-4-methylphenyl)butan-2-one

Traditional Name

3-(2-hydroxy-4-methylphenyl)butan-2-one

CAS Registry Number

83810-64-4

SMILES

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

InChI Identifier

InChI=1S/C11H14O2/c1-7-4-5-10(11(13)6-7)8(2)9(3)12/h4-6,8,13H,1-3H3

InChI Key

YWKYLGVKGIAHDU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Phenylpropane
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
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

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038179)

Source

Endogenous

Endogenous (HMDB: HMDB0038179)

Plant

Plant (HMDB: HMDB0038179)

Animal

Animal (HMDB: HMDB0038179)

Exogenous

Food

Food (HMDB: HMDB0038179)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038179)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038179)

Cellular process

Cell signaling (HMDB: HMDB0038179)

Biochemical process

Lipid transport (HMDB: HMDB0038179)

Role

Biological role

Energy storage (HMDB: HMDB0038179)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038179)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67 - 68 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4547 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	0.38 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.69	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.51 m³·mol⁻¹	ChemAxon
Polarizability	19.9 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	142.74	31661259
DarkChem	[M-H]-	138.208	31661259
DeepCCS	[M+H]+	144.223	30932474
DeepCCS	[M-H]-	141.86	30932474
DeepCCS	[M-2H]-	176.74	30932474
DeepCCS	[M+Na]+	151.341	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	140.7	32859911
AllCCS	[M+Na-2H]-	141.6	32859911
AllCCS	[M+HCOO]-	142.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(2-Hydroxy-4-methylphenyl)-2-butanone	CC(C(C)=O)C1=C(O)C=C(C)C=C1	2575.0	Standard polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone	CC(C(C)=O)C1=C(O)C=C(C)C=C1	1443.6	Standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone	CC(C(C)=O)C1=C(O)C=C(C)C=C1	1547.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TMS,isomer #1	CC(=O)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C	1526.4	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TMS,isomer #2	CC(O[Si](C)(C)C)=C(C)C1=CC=C(C)C=C1O	1630.1	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TMS,isomer #3	C=C(O[Si](C)(C)C)C(C)C1=CC=C(C)C=C1O	1540.2	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)C1=CC=C(C)C=C1O[Si](C)(C)C	1698.6	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)C1=CC=C(C)C=C1O[Si](C)(C)C	1711.7	Standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C	1583.9	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C	1652.6	Standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TBDMS,isomer #1	CC(=O)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C(C)(C)C	1762.7	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C(C)C1=CC=C(C)C=C1O	1892.3	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC=C(C)C=C1O	1793.8	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)C1=CC=C(C)C=C1O[Si](C)(C)C(C)(C)C	2187.7	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)C1=CC=C(C)C=C1O[Si](C)(C)C(C)(C)C	2180.8	Standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C(C)(C)C	2063.7	Semi standard non polar	33892256
3-(2-Hydroxy-4-methylphenyl)-2-butanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC=C(C)C=C1O[Si](C)(C)C(C)(C)C	2090.2	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-(2-Hydroxy-4-methylphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-7900000000-9e60f938d9473ca8fffd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-4290000000-2d95b8d73c21c97e6502	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-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 - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 10V, Positive-QTOF	splash10-004i-0900000000-82bd1df9efcb3d717fe6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 20V, Positive-QTOF	splash10-004i-4900000000-447f794fe28f1d277d48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 40V, Positive-QTOF	splash10-0wmi-7900000000-c8455e95edffd4d7d0ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 10V, Negative-QTOF	splash10-004i-0900000000-079baa3e33789ef2a7a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 20V, Negative-QTOF	splash10-056r-1900000000-f2e18e22985a2f90c3e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 40V, Negative-QTOF	splash10-0aou-7900000000-5660d42b480917102634	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 10V, Positive-QTOF	splash10-052r-2900000000-c0f75de45763cb75deab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 20V, Positive-QTOF	splash10-0006-9400000000-d353f0e507aee67a016e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 40V, Positive-QTOF	splash10-0006-9200000000-de70464249a0a237955a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 10V, Negative-QTOF	splash10-004i-0900000000-1ccd690a61b3f7466655	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 20V, Negative-QTOF	splash10-0a4i-4900000000-5c4b030f3937cdbb5f8a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-4-methylphenyl)-2-butanone 40V, Negative-QTOF	splash10-066u-8900000000-be71e952c505c742dbaf	2021-09-23	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

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

FDB017418

KNApSAcK ID

Not Available

Chemspider ID

15063426

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20472052

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1619881

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-(2-Hydroxy-4-methylphenyl)-2-butanone (HMDB0038179)

MOL for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

3D MOL for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

3D SDF for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

3D-SDF for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

PDB for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

3D PDB for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

SMILES for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

INCHI for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

Structure for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

3D Structure for HMDB0038179 (3-(2-Hydroxy-4-methylphenyl)-2-butanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra