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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:08:55 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036079

Secondary Accession Numbers

HMDB36079

Metabolite Identification

Common Name

Dihydrocarvone

Description

Dihydrocarvone, also known as menth-8-en-2-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Dihydrocarvone is an essentially neutral compound. It has a warm herbal, minty taste with a spicy¬†minty¬†woody¬†camphoreous flavour ( Ref:DOI ). Dihydrocarvone is found in highest concentrations in spearmints, caraway, and wild celeries and was detected celery stalks, dills, pepper (spice), and peppermints. This could make dihydrocarvone a potential biomarker for the consumption of these foods. Dihydrocarvone is also found in cannabis plants (PMID:6991645 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0036079
HETATM    1  C1  UNL     1       2.273   1.619   1.145  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.884   0.366   1.115  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.552  -0.575   2.056  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.834  -0.055   0.184  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.379  -0.642   0.895  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.254  -1.233  -0.221  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.860  -0.072  -0.966  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.844  -0.527  -2.010  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.753   0.723  -1.554  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.740   1.044  -2.720  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.350   1.112  -0.637  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.051   1.891   1.847  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.834   2.351   0.493  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.692  -1.580   1.615  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.857  -0.670   2.935  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.482  -0.139   2.449  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.193  -0.868  -0.497  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.109  -1.415   1.626  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.959   0.195   1.306  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.567  -1.768  -0.906  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.013  -1.920   0.201  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.411   0.567  -0.232  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.670   0.118  -2.915  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.897  -0.324  -1.714  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.694  -1.565  -2.339  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.220   1.484  -1.219  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.072   1.884   0.051  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   10   10   11
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-5-(1-methylethenyl)cyclohexanone	ChEBI
2-Methyl-5-isopropenylcyclohexanone	ChEBI
5-Isopropenyl-2-methylcyclohexanone	ChEBI
8-p-Menthen-2-one	ChEBI
Menth-8-en-2-one	ChEBI
p-Menth-8(9)-en-2-one	ChEBI
3-Isopropenyl-6-methylcyclohexanone	MeSH
p-Menth-8-en-2-one	MeSH
a Dihydrocarvone	ChEBI, HMDB
1,6-Dihydrocarvone	HMDB
2-Methyl-5-(1-methylethenyl)-cyclohexanone	HMDB
2-Methyl-5-(1-methylethenyl)cyclohexanone, 9ci	HMDB
2-Methyl-5-(1-methylvinyl)cyclohexan-1-one	HMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohexanone	HMDB
FEMA 3565	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one

Traditional Name

dihydrocarvone

CAS Registry Number

7764-50-3

SMILES

CC1CCC(CC1=O)C(C)=C

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3

InChI Key

AZOCECCLWFDTAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dihydrocarvones (CHEBI:23733 )
an iso dihydrocarvone (CPD-10042 )

Ontology

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036079)

Source

Endogenous

Endogenous (HMDB: HMDB0036079)

Plant

Plant (HMDB: HMDB0036079)

Animal

Animal (HMDB: HMDB0036079)

Exogenous

Food

Food (HMDB: HMDB0036079)

Celery stalks (FooDB: FOOD00215)

Exogenous (HMDB: HMDB0036079)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036079)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036079)

Lipid metabolism pathway (HMDB: HMDB0036079)

Cellular process

Cell signaling (HMDB: HMDB0036079)

Biochemical process

Lipid transport (HMDB: HMDB0036079)

Role

Biological role

Energy source (HMDB: HMDB0036079)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036079)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036079)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	87.00 to 88.00 °C. @ 6.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.02 mg/mL at 15 °C	Not Available
LogP	2.85	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.7	ChemAxon
logS	-2.4	ALOGPS
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	1	ChemAxon
Refractivity	46.3 m³·mol⁻¹	ChemAxon
Polarizability	18.27 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]+	135.669	31661259
DarkChem	[M-H]-	128.893	31661259
DeepCCS	[M+H]+	141.016	30932474
DeepCCS	[M-H]-	137.269	30932474
DeepCCS	[M-2H]-	174.773	30932474
DeepCCS	[M+Na]+	150.232	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.9	32859911
AllCCS	[M+Na]+	138.1	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	140.4	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. Predicted by Afia on May 17, 2022.	5.08 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2115.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	526.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	301.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	554.0 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	677.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1185.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	408.6 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	1300.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	399.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	480.8 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	25.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocarvone	CC1CCC(CC1=O)C(C)=C	1663.1	Standard polar	33892256
Dihydrocarvone	CC1CCC(CC1=O)C(C)=C	1159.5	Standard non polar	33892256
Dihydrocarvone	CC1CCC(CC1=O)C(C)=C	1201.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocarvone,1TMS,isomer #1	C=C(C)C1CCC(C)=C(O[Si](C)(C)C)C1	1364.8	Semi standard non polar	33892256
Dihydrocarvone,1TMS,isomer #1	C=C(C)C1CCC(C)=C(O[Si](C)(C)C)C1	1350.5	Standard non polar	33892256
Dihydrocarvone,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C(C)CC1	1308.8	Semi standard non polar	33892256
Dihydrocarvone,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C(C)CC1	1320.4	Standard non polar	33892256
Dihydrocarvone,1TBDMS,isomer #1	C=C(C)C1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1	1599.6	Semi standard non polar	33892256
Dihydrocarvone,1TBDMS,isomer #1	C=C(C)C1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1	1530.5	Standard non polar	33892256
Dihydrocarvone,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)CC1	1550.8	Semi standard non polar	33892256
Dihydrocarvone,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)CC1	1489.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00m3-9100000000-fa9716dc62a7dad68748	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0159-9200000000-204b096f608a1da059c5	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Positive-QTOF	splash10-0udi-1900000000-11c8140e07776f4ec8a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Positive-QTOF	splash10-0zfr-9700000000-aa93539a6a6d13e993c5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Positive-QTOF	splash10-100r-9000000000-2654db8ab644e2360913	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-869565234ac5daf7c3b2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Negative-QTOF	splash10-0udi-0900000000-66279fba8a75e05ec84b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Negative-QTOF	splash10-0kto-9500000000-19dd52dd1ac87fa23abf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Negative-QTOF	splash10-0udi-1900000000-6d20364e296745592a69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Negative-QTOF	splash10-00kn-6900000000-23186e60d8ffad674527	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Positive-QTOF	splash10-0gws-7900000000-b08efab8959a09a26216	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Positive-QTOF	splash10-000x-9200000000-13ccbe770389182b9c06	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Positive-QTOF	splash10-0006-9000000000-4b6afc70d0efd7f97f15	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24473

PDB ID

Not Available

ChEBI ID

23733

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1031221

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dihydrocarvone (HMDB0036079)

MOL for HMDB0036079 (Dihydrocarvone)

3D MOL for HMDB0036079 (Dihydrocarvone)

3D SDF for HMDB0036079 (Dihydrocarvone)

3D-SDF for HMDB0036079 (Dihydrocarvone)

PDB for HMDB0036079 (Dihydrocarvone)

3D PDB for HMDB0036079 (Dihydrocarvone)

SMILES for HMDB0036079 (Dihydrocarvone)

INCHI for HMDB0036079 (Dihydrocarvone)

Structure for HMDB0036079 (Dihydrocarvone)

3D Structure for HMDB0036079 (Dihydrocarvone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra