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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:28:50 UTC

Update Date

2023-02-21 17:23:32 UTC

HMDB ID

HMDB0033723

Secondary Accession Numbers

HMDB33723

Metabolite Identification

Common Name

4-(4-Hydroxyphenyl)-2-butanone

Description

4-(4-Hydroxyphenyl)-2-butanone, also known as (p-hydroxybenzyl)acetone or 4-(3-oxobutyl)phenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-(4-Hydroxyphenyl)-2-butanone is a sweet, berry, and floral tasting compound. 4-(4-Hydroxyphenyl)-2-butanone has been detected, but not quantified in, fruits and red raspberries (Rubus idaeus). This could make 4-(4-hydroxyphenyl)-2-butanone a potential biomarker for the consumption of these foods. 4-(4-Hydroxyphenyl)-2-butanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-(4-Hydroxyphenyl)-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  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   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  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    4    5                                                  
CONECT   10    6    7   12                                                  
CONECT   11    8                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(p-Hydroxybenzyl)acetone	ChEBI
1-(4-Hydroxyphenyl)-3-butanone	ChEBI
1-(p-Hydroxyphenyl)-3-butanone	ChEBI
4-(3-Oxobutyl)phenol	ChEBI
4-(p-Hydroxyphenyl)-2-butanone	ChEBI
4-Hydroxybenzylacetone	ChEBI
p-Hydroxybenzyl acetone	ChEBI
p-Hydroxyphenylbutan-2-one	ChEBI
4-(4-Hydroxyphenyl)butan-2-one	MeSH
Betuligenol	MeSH
Oxyphenalon	MeSH
p-Hydroxybenzylacetone	MeSH
Raspberry ketone	MeSH
FEMA 2588	HMDB
Frambinone	HMDB
P-Hydroxyphenylbutanone	HMDB
Rasberry ketone	HMDB
Rasketone	HMDB
Rheosmin	HMDB
Rheosmine	HMDB
4-(4-Hydroxyphenyl)-2-butanone	ChEBI

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

4-(4-hydroxyphenyl)butan-2-one

Traditional Name

raspberry ketone

CAS Registry Number

5471-51-2

SMILES

CC(=O)CCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3

InChI Key

NJGBTKGETPDVIK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:68656 )
methyl ketone (CHEBI:68656 )
a polyketide (CPD-8647 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033723)
Cytoplasm (HMDB: HMDB0033723)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033723)

Source

Exogenous

Food

Food (HMDB: HMDB0033723)

Fruit

Berry

Red raspberry (FooDB: FOOD00162)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033723)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033723)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	82.5 °C	Not Available
Boiling Point	200.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.309 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.8 g/L	ALOGPS
logP	2.08	ALOGPS
logP	2.08	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.51	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	3	ChemAxon
Refractivity	47.5 m³·mol⁻¹	ChemAxon
Polarizability	18.02 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]+	138.802	31661259
DarkChem	[M-H]-	135.222	31661259
DeepCCS	[M+H]+	135.8	30932474
DeepCCS	[M-H]-	132.836	30932474
DeepCCS	[M-2H]-	169.771	30932474
DeepCCS	[M+Na]+	145.309	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	130.9	32859911
AllCCS	[M+NH4]+	139.4	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(4-Hydroxyphenyl)-2-butanone	CC(=O)CCC1=CC=C(O)C=C1	2703.1	Standard polar	33892256
4-(4-Hydroxyphenyl)-2-butanone	CC(=O)CCC1=CC=C(O)C=C1	1518.2	Standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone	CC(=O)CCC1=CC=C(O)C=C1	1567.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #1	CC(=O)CCC1=CC=C(O[Si](C)(C)C)C=C1	1612.6	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #2	CC(=CCC1=CC=C(O)C=C1)O[Si](C)(C)C	1754.9	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #3	C=C(CCC1=CC=C(O)C=C1)O[Si](C)(C)C	1773.2	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #1	CC(=CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	1795.0	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #1	CC(=CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	1713.6	Standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	1717.6	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	1671.5	Standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #1	CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1863.3	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #2	CC(=CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C	1994.1	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #3	C=C(CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C	1994.4	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #1	CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2277.2	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #1	CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2211.2	Standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2217.0	Semi standard non polar	33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2141.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone EI-B (Non-derivatized)	splash10-0a4i-5900000000-e86a807414e04733339d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone EI-B (Non-derivatized)	splash10-0a4i-5900000000-e86a807414e04733339d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-7900000000-f17914de6993b2049156	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-7920000000-cb2a2ee41573305c6a88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 75V, Positive-QTOF	splash10-00di-5900000000-0a8b7fe2b9f1fb76ce6e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 90V, Positive-QTOF	splash10-00di-9700000000-a9d4506fbf302f416ea2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 15V, Positive-QTOF	splash10-00di-0900000000-1fd0e582b4ef7431f131	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 30V, Positive-QTOF	splash10-00di-0900000000-e2f8dc46c8f71782dd3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 45V, Positive-QTOF	splash10-00di-1900000000-23fa756b8ca68a3f84c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 60V, Positive-QTOF	splash10-00di-2900000000-9db04c385775387df3fa	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-014j-0900000000-74c218754158b5095cc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-05mk-1900000000-574dbe1fc7ce6561ea62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-0zi3-9700000000-7faac7cc428fe0e255a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-03di-0900000000-2a84eaaa97fd7592296a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-03di-2900000000-7a3bca10c8cf4304c6e8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-0a4l-9500000000-e985da2b00cefdf6bc1c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-0a4i-9200000000-a1b1c874ab7b923bb7c3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-0a4i-9400000000-713daf098b2527154db2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-052f-9000000000-d9d01a460fd0c6839ef1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-066s-1900000000-df8baa8c079c2eea5974	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-0a4i-3900000000-aadb08876da6bfd67b20	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-004i-9300000000-041ace743c31c59af451	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

FDB011843

KNApSAcK ID

C00041092

Chemspider ID

20347

KEGG Compound ID

Not Available

BioCyc ID

CPD-8647

BiGG ID

Not Available

Wikipedia Link

Raspberry_ketone

METLIN ID

Not Available

PubChem Compound

21648

PDB ID

Not Available

ChEBI ID

68656

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020771

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-(4-Hydroxyphenyl)-2-butanone → 3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4-(4-Hydroxyphenyl)-2-butanone → [4-(3-oxobutyl)phenyl]oxidanesulfonic acid	details

Showing metabocard for 4-(4-Hydroxyphenyl)-2-butanone (HMDB0033723)

MOL for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

3D MOL for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

3D SDF for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

3D-SDF for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

PDB for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

3D PDB for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

SMILES for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

INCHI for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

Structure for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

3D Structure for HMDB0033723 (4-(4-Hydroxyphenyl)-2-butanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions