AFCDB: 4-(4-Hydroxyphenyl)-2-butanone (FDB011843)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:51 UTC

Update date

2019-11-26 03:05:33 UTC

Primary ID

FDB011843

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. Based on a literature review a significant number of articles have been published on 4-(4-Hydroxyphenyl)-2-butanone.

CAS Number

5471-51-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C10H12O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 73.15%; H 7.37%; O 19.49%	DFC
Melting Point	Mp 82.5°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	4-(4-Hydroxyphenyl)-2-butanone, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-e86a807414e04733339d	Spectrum
GC-MS	4-(4-Hydroxyphenyl)-2-butanone, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-e86a807414e04733339d	Spectrum
Predicted GC-MS	4-(4-Hydroxyphenyl)-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-7900000000-f17914de6993b2049156	Spectrum
Predicted GC-MS	4-(4-Hydroxyphenyl)-2-butanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-7920000000-cb2a2ee41573305c6a88	Spectrum
Predicted GC-MS	4-(4-Hydroxyphenyl)-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-(4-Hydroxyphenyl)-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-5900000000-0a8b7fe2b9f1fb76ce6e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-9700000000-a9d4506fbf302f416ea2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-0900000000-1fd0e582b4ef7431f131	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0900000000-e2f8dc46c8f71782dd3a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-1900000000-23fa756b8ca68a3f84c8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-2900000000-9db04c385775387df3fa	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-74c218754158b5095cc9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-1900000000-574dbe1fc7ce6561ea62	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi3-9700000000-7faac7cc428fe0e255a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-2a84eaaa97fd7592296a	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2900000000-7a3bca10c8cf4304c6e8	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9500000000-e985da2b00cefdf6bc1c	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9200000000-a1b1c874ab7b923bb7c3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9400000000-713daf098b2527154db2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-d9d01a460fd0c6839ef1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066s-1900000000-df8baa8c079c2eea5974	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-aadb08876da6bfd67b20	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9300000000-041ace743c31c59af451	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

20347

ChEMBL ID

CHEMBL105912

KEGG Compound ID

Not Available

Pubchem Compound ID

21648

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33723

CRC / DFC (Dictionary of Food Compounds) ID

GZX39-H:GZX39-H

EAFUS ID

1777

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

5471-51-2

GoodScent ID

rw1020771

SuperScent ID

21648

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
raspberry	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
berry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
jam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ripe	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

4-(4-Hydroxyphenyl)-2-butanone (FDB011843)

Structure for FDB011843 (4-(4-Hydroxyphenyl)-2-butanone)