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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:14:15 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036176

Secondary Accession Numbers

HMDB36176

Metabolite Identification

Common Name

3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one

Description

3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one is a sweet and maple tasting compound. Based on a literature review very few articles have been published on 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one.

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-Cyclopenten-1-one, 2-hydroxy-3-ethyl-4-methyl	HMDB
3-Ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one	HMDB
3-Ethyl-4-methyl-1,2-cyclopentanedione	HMDB
3-Ethyl-4-methylcyclotene	HMDB
FEMA 3453	HMDB

Chemical Formula

C₈H₁₂O₂

Average Molecular Weight

140.1797

Monoisotopic Molecular Weight

140.083729628

IUPAC Name

3-ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one

Traditional Name

3-ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one

CAS Registry Number

42348-12-9

SMILES

CCC1=C(O)C(=O)CC1C

InChI Identifier

InChI=1S/C8H12O2/c1-3-6-5(2)4-7(9)8(6)10/h5,10H,3-4H2,1-2H3

InChI Key

RSVAFMGHIDKYKB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Enol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cell membrane (HMDB: HMDB0036176)

Cellular substructure

Extracellular (HMDB: HMDB0036176)
Membrane (HMDB: HMDB0036176)

Source

Endogenous

Endogenous (HMDB: HMDB0036176)

Exogenous

Food

Food (HMDB: HMDB0036176)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036176)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036176)

Nutrient

Nutrient (HMDB: HMDB0036176)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036176)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0036176)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	260.00 to 261.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.615 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.9 g/L	ALOGPS
logP	0.78	ALOGPS
logP	1.5	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-3.6	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	1	ChemAxon
Refractivity	40.14 m³·mol⁻¹	ChemAxon
Polarizability	15.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	135.685	30932474
DeepCCS	[M-H]-	133.36	30932474
DeepCCS	[M-2H]-	169.186	30932474
DeepCCS	[M+Na]+	143.969	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	125.9	32859911
AllCCS	[M+NH4]+	134.6	32859911
AllCCS	[M+Na]+	135.8	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one	CCC1=C(O)C(=O)CC1C	1830.8	Standard polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one	CCC1=C(O)C(=O)CC1C	1139.4	Standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one	CCC1=C(O)C(=O)CC1C	1131.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,1TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(=O)CC1C	1304.1	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,1TMS,isomer #2	CCC1=C(O)C(O[Si](C)(C)C)=CC1C	1355.9	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,2TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1C	1460.6	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,2TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1C	1490.0	Standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,1TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1C	1543.4	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,1TBDMS,isomer #2	CCC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CC1C	1566.1	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1C	1919.1	Semi standard non polar	33892256
3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1C	1831.5	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-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0297-9400000000-4b3317986c561390163c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one GC-MS (1 TMS) - 70eV, Positive	splash10-00u2-7900000000-1a0ed0720fcf9e1bb47b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 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-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-0006-1900000000-4cd185bcce827d445255	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-014l-9300000000-a9452a5152386b956d32	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-00kf-9000000000-e9983bcc6d60d3c3198a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-000i-0900000000-b3da58baad7dae732359	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-000i-2900000000-6b9cc522c39855314da5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-05to-9500000000-94fe88579725bf9ebd11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-00dl-0900000000-2c2d4d9ef2fed6fb60b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-00ej-9500000000-716692aea37c28cfa058	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0fr6-9000000000-f582c192be669d55ff2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-000i-0900000000-a5734f49b62679635a5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-000i-3900000000-517b45b941dade6f9499	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-000f-9500000000-a47dc1e466ae0b6e7b76	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB015030

KNApSAcK ID

Not Available

Chemspider ID

460789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

528698

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036261

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 3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one (HMDB0036176)

MOL for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

3D MOL for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

3D SDF for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

3D-SDF for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

PDB for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

3D PDB for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

SMILES for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

INCHI for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

Structure for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

3D Structure for HMDB0036176 (3-Ethyl-2-hydroxy-4-methyl-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra