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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:52:10 UTC

Update Date

2023-02-21 17:28:10 UTC

HMDB ID

HMDB0040338

Secondary Accession Numbers

HMDB40338

Metabolite Identification

Common Name

3,5,5-Trimethyl-3-cyclohexen-1-one

Description

3,5,5-Trimethyl-3-cyclohexen-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-3-cyclohexen-1-one has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and saffrons (Crocus sativus). This could make 3,5,5-trimethyl-3-cyclohexen-1-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5,5-Trimethyl-3-cyclohexen-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
.beta-isophorone	HMDB
3,5,5-Trimethyl-3-cyclohexene-1-one	HMDB
3,5,5-Trimethylcyclohex-3-enone	HMDB
b-Isophorone	HMDB
b-Phorone	HMDB
beta -Isophorone	HMDB
beta -Phorone	HMDB
beta-Isophorone	HMDB
beta-Phorone	HMDB
Crocusatin e	HMDB

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

3,5,5-trimethylcyclohex-3-en-1-one

Traditional Name

3,5,5-trimethylcyclohex-3-en-1-one

CAS Registry Number

471-01-2

SMILES

CC1=CC(C)(C)CC(=O)C1

InChI Identifier

InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3

InChI Key

LKOKKQDYMZUSCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
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: HMDB0040338)

Source

Endogenous

Endogenous (HMDB: HMDB0040338)

Plant

Plant (HMDB: HMDB0040338)

Exogenous

Food

Food (HMDB: HMDB0040338)

Herb and spice

Spice

Saffron (FooDB: FOOD00063)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0040338)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0040338)

Role

Biological role

Energy source (HMDB: HMDB0040338)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040338)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	189.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	873.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.180 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.57 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.96	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	16.62	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.67 m³·mol⁻¹	ChemAxon
Polarizability	16.27 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
DarkChem	[M+H]+	131.145	31661259
DarkChem	[M-H]-	126.852	31661259
DeepCCS	[M+H]+	135.69	30932474
DeepCCS	[M-H]-	132.121	30932474
DeepCCS	[M-2H]-	169.4	30932474
DeepCCS	[M+Na]+	144.884	30932474
AllCCS	[M+H]+	126.7	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.2	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	134.1	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.	3.92 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9812 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1897.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	429.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	256.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	388.9 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	513.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1009.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.7 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	917.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.0 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	22.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-3-cyclohexen-1-one	CC1=CC(C)(C)CC(=O)C1	1392.9	Standard polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one	CC1=CC(C)(C)CC(=O)C1	994.7	Standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one	CC1=CC(C)(C)CC(=O)C1	1064.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(C)(C)CC(O[Si](C)(C)C)=C1	1268.6	Semi standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(C)(C)CC(O[Si](C)(C)C)=C1	1241.6	Standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #2	CC1=CC(C)(C)C=C(O[Si](C)(C)C)C1	1203.8	Semi standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #2	CC1=CC(C)(C)C=C(O[Si](C)(C)C)C1	1174.7	Standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(C)(C)CC(O[Si](C)(C)C(C)(C)C)=C1	1470.4	Semi standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(C)(C)CC(O[Si](C)(C)C(C)(C)C)=C1	1480.6	Standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #2	CC1=CC(C)(C)C=C(O[Si](C)(C)C(C)(C)C)C1	1424.1	Semi standard non polar	33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #2	CC1=CC(C)(C)C=C(O[Si](C)(C)C(C)(C)C)C1	1407.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-9200000000-44cce750b46a7c0248bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-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 - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Positive-QTOF	splash10-000i-0900000000-ae6ee4405608e5f7a0c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Positive-QTOF	splash10-000i-5900000000-7e83a4ecb52be1c7aca0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Positive-QTOF	splash10-052k-9000000000-c4a885c2890f13a74403	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Negative-QTOF	splash10-000i-0900000000-12e4fd56237f81a516de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Negative-QTOF	splash10-000i-0900000000-57e3939106050a782b1a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Negative-QTOF	splash10-000f-9600000000-89b45e9ad286053f2766	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Negative-QTOF	splash10-000i-1900000000-968397034843fdc6f07d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Negative-QTOF	splash10-00dl-8900000000-c704e2adee956737100d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Positive-QTOF	splash10-0080-9700000000-8542f13911062f7bc78f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Positive-QTOF	splash10-0a6r-9100000000-7c34a35ebd7a83d066ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Positive-QTOF	splash10-057u-9000000000-5a30ebfc7a84d63439d2	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB020063

KNApSAcK ID

C00032863

Chemspider ID

9704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10108

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1506341

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 3,5,5-Trimethyl-3-cyclohexen-1-one (HMDB0040338)

MOL for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

3D MOL for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

3D SDF for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

3D-SDF for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

PDB for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

3D PDB for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

SMILES for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

INCHI for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

Structure for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

3D Structure for HMDB0040338 (3,5,5-Trimethyl-3-cyclohexen-1-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra