Showing Compound 4-Mercapto-4-methyl-2-pentanone (FDB008119)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:56 UTC

Update date

2020-02-24 19:10:49 UTC

Primary ID

FDB008119

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Mercapto-4-methyl-2-pentanone

Description

4-Mercapto-4-methyl-2-pentanone, also known as 4-sulfanyl-4-methylpentan-2-one or 4-methyl-4-sulfanyl-2-pentanone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 4-mercapto-4-methyl-2-pentanone is considered to be an oxygenated hydrocarbon. 4-Mercapto-4-methyl-2-pentanone is a blackcurrant, box tree, and cat-urine tasting compound. 4-Mercapto-4-methyl-2-pentanone has been detected, but not quantified in, alcoholic beverages and grape wine. This could make 4-mercapto-4-methyl-2-pentanone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Mercapto-4-methyl-2-pentanone.

CAS Number

19872-52-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-Pentanone, 4-mercapto-4-methyl-	biospider
4-Mercapto-4-methyl-2-pentanone	ChEBI
4-mercapto-4-Methyl-pentan-2-one	HMDB
4-Mercapto-4-methyl-pentan-2-one	biospider
4-mercapto-4-Methylpentan-2-one	HMDB
4-Mercapto-4-methylpentan-2-one	biospider
4-Methyl-4-mercapto-2-pentanone	ChEBI
4-methyl-4-mercapto-2-pentanone	biospider
4-Methyl-4-mercapto-pentan-2-one	HMDB
4-Methyl-4-mercaptopentan-2-one	ChEBI

Showing 1 to 10 of 16 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.78 m³·mol⁻¹	ChemAxon
Polarizability	14.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12OS

IUPAC name

4-methyl-4-sulfanylpentan-2-one

InChI Identifier

InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

InChI Key

QRNZMFDCKKEPSX-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)CC(C)(C)S

Average Molecular Weight

132.224

Monoisotopic Molecular Weight

132.060885696

Classification

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Alkylthiol
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alkanethiol (CHEBI:77856 )
methyl ketone (CHEBI:77856 )
Oxygenated hydrocarbons (LMFA12000335 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp0.12 55-58°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 54.50%; H 9.15%; O 12.10%; S 24.25%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-Mercapto-4-methyl-2-pentanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002f-9100000000-8e9ff8d3dd57a941e176	Spectrum
Predicted GC-MS	4-Mercapto-4-methyl-2-pentanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-3900000000-f7c166c594ab2f5bd9e6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-7900000000-415b660e2464f89dc70e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-cf87bb56a906d8284051	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001j-7900000000-67facb7cefc788001bd4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-9600000000-5a2f4ae474d4a47b0beb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-7653612fbae5886b1570	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9100000000-5b554632046f18361f55	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-9000000000-e5eeba93e8d05760b98b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004m-9000000000-3a7dea1da5a4cd927037	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-9000000000-99d12173b922c0f09a40	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-53764c8f862c3e9527d9	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

79650

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

88290

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31519

CRC / DFC (Dictionary of Food Compounds) ID

DCH44-R:DCH44-R

EAFUS ID

2186

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

19872-52-7

GoodScent ID

rw1038251

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
blackcurrant	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
box tree	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
boxtree	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
cat-urine	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
meaty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sulfurous	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.