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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:05:01 UTC

Update Date

2023-02-21 17:28:18 UTC

HMDB ID

HMDB0040526

Secondary Accession Numbers

HMDB40526

Metabolite Identification

Common Name

3,4,4-Trimethyl-1,2-cyclopentanedione

Description

3,4,4-Trimethyl-1,2-cyclopentanedione 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. 3,4,4-Trimethyl-1,2-cyclopentanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3,4,4-trimethyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,4,4-Trimethyl-1,2-cyclopentanedione.

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-Hydroxy-3,4,4-trimethyl-2-cyclopenten-1-one	HMDB

Chemical Formula

C₈H₁₂O₂

Average Molecular Weight

140.1797

Monoisotopic Molecular Weight

140.083729628

IUPAC Name

2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one

Traditional Name

2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one

CAS Registry Number

86702-81-0

SMILES

CC1=C(O)C(=O)CC1(C)C

InChI Identifier

InChI=1S/C8H12O2/c1-5-7(10)6(9)4-8(5,2)3/h10H,4H2,1-3H3

InChI Key

LTRJTLUJZFBIEN-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040526)

Source

Endogenous

Endogenous (HMDB: HMDB0040526)

Plant

Coffea (HMDB: HMDB0040526)

Exogenous

Food

Food (HMDB: HMDB0040526)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0040526)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0040526)

Role

Biological role

Energy source (HMDB: HMDB0040526)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040526)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	242.39 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1198 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.334 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.2 g/L	ALOGPS
logP	0.77	ALOGPS
logP	1.35	ChemAxon
logS	-0.8	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	0	ChemAxon
Refractivity	40.01 m³·mol⁻¹	ChemAxon
Polarizability	15.17 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]+	135.035	30932474
DeepCCS	[M-H]-	132.106	30932474
DeepCCS	[M-2H]-	168.334	30932474
DeepCCS	[M+Na]+	143.825	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.7	32859911
AllCCS	[M+NH4]+	133.2	32859911
AllCCS	[M+Na]+	134.4	32859911
AllCCS	[M-H]-	128.9	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.51 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5968 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1649.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	362.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	492.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	492.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	831.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	349.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1177.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	299.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4,4-Trimethyl-1,2-cyclopentanedione	CC1=C(O)C(=O)CC1(C)C	1768.8	Standard polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione	CC1=C(O)C(=O)CC1(C)C	1083.2	Standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione	CC1=C(O)C(=O)CC1(C)C	1096.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4,4-Trimethyl-1,2-cyclopentanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CC1(C)C	1283.9	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=CC1(C)C	1291.0	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1(C)C	1392.2	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1(C)C	1401.5	Standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1(C)C	1524.7	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1492.9	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1823.2	Semi standard non polar	33892256
3,4,4-Trimethyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1753.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btc-9200000000-8d54fc10534874218d8e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione GC-MS (1 TMS) - 70eV, Positive	splash10-0592-9600000000-346c9ac818bcabd03ec6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 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 - 3,4,4-Trimethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-0006-0900000000-e2ac0c91dc2f06c3b35e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-014l-9500000000-64d386451e4f7af00570	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-014i-9000000000-2566a0c87a9381e4f7be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-000i-0900000000-c81551f418a6e4693367	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-000i-1900000000-e4b7ade85f6c31e0b611	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-053u-9200000000-6e53611e48885c49a4f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-0006-4900000000-23c216121d2661b16256	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-0a4l-9000000000-0fd635ebe16d6479f032	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-00kf-9000000000-5e4c2e276d021f43aab0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-000i-0900000000-12a5ab1d6612b1268d64	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-000i-3900000000-4367f5af298690fd8745	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,4-Trimethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-006x-9600000000-d884dc8a88672aa56df1	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

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

FDB020293

KNApSAcK ID

Not Available

Chemspider ID

4934163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428785

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1619121

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 3,4,4-Trimethyl-1,2-cyclopentanedione (HMDB0040526)

MOL for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

3D MOL for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

3D SDF for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

3D-SDF for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

PDB for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

3D PDB for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

SMILES for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

INCHI for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

Structure for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

3D Structure for HMDB0040526 (3,4,4-Trimethyl-1,2-cyclopentanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra