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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:15:19 UTC

Update Date

2023-02-21 17:25:32 UTC

HMDB ID

HMDB0037012

Secondary Accession Numbers

HMDB37012

Metabolite Identification

Common Name

2-Hydroxy-p-mentha-1,8-dien-6-one

Description

2-Hydroxy-p-mentha-1,8-dien-6-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. Based on a literature review a small amount of articles have been published on 2-Hydroxy-p-mentha-1,8-dien-6-one.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8    9                                                       
CONECT    5    8   10                                                       
CONECT    6    1    2    8                                                  
CONECT    7    3    9   10                                                  
CONECT    8    4    5    6                                                  
CONECT    9    4    7   11                                                  
CONECT   10    5    7   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one	HMDB
6-Hydroxycarvone	HMDB
P-Menth-8-ene-2,6-dione	HMDB

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

3-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

Traditional Name

3-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

CAS Registry Number

51200-86-3

SMILES

CC(=C)C1CC(O)=C(C)C(=O)C1

InChI Identifier

InChI=1S/C10H14O2/c1-6(2)8-4-9(11)7(3)10(12)5-8/h8,11H,1,4-5H2,2-3H3

InChI Key

XPEAPCMHDFIXFL-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
Cyclohexenone
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: HMDB0037012)

Source

Endogenous

Endogenous (HMDB: HMDB0037012)

Plant

Plant (HMDB: HMDB0037012)

Animal

Animal (HMDB: HMDB0037012)

Exogenous

Food

Food (HMDB: HMDB0037012)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037012)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037012)

Cellular process

Cell signaling (HMDB: HMDB0037012)

Biochemical process

Lipid transport (HMDB: HMDB0037012)

Role

Biological role

Energy storage (HMDB: HMDB0037012)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037012)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	267.00 to 268.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	879.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.563 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.57 g/L	ALOGPS
logP	0.88	ALOGPS
logP	1.73	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-5.5	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	49.22 m³·mol⁻¹	ChemAxon
Polarizability	18.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	140.428	30932474
DeepCCS	[M-H]-	137.783	30932474
DeepCCS	[M-2H]-	174.053	30932474
DeepCCS	[M+Na]+	149.591	30932474
AllCCS	[M+H]+	135.9	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.1	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-p-mentha-1,8-dien-6-one	CC(=C)C1CC(O)=C(C)C(=O)C1	2148.0	Standard polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one	CC(=C)C1CC(O)=C(C)C(=O)C1	1302.1	Standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one	CC(=C)C1CC(O)=C(C)C(=O)C1	1349.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-p-mentha-1,8-dien-6-one,1TMS,isomer #1	C=C(C)C1CC(=O)C(C)=C(O[Si](C)(C)C)C1	1474.8	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C(C)=C(O)C1	1514.2	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C1	1567.7	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C1	1573.3	Standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,1TBDMS,isomer #1	C=C(C)C1CC(=O)C(C)=C(O[Si](C)(C)C(C)(C)C)C1	1724.8	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O)C1	1746.0	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C1	2041.0	Semi standard non polar	33892256
2-Hydroxy-p-mentha-1,8-dien-6-one,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C1	1969.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ox-9300000000-cff4a10a0845a0203906	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one GC-MS (1 TMS) - 70eV, Positive	splash10-00g3-9420000000-55b48a2a4beb4be03e7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-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 - 2-Hydroxy-p-mentha-1,8-dien-6-one 10V, Positive-QTOF	splash10-014i-0900000000-ff205246d8ca3740b014	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 20V, Positive-QTOF	splash10-014i-3900000000-1aae2fbb275af56d5d26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 40V, Positive-QTOF	splash10-0159-9000000000-a2be88ac6872e59d2690	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 10V, Negative-QTOF	splash10-014i-0900000000-2731114572ecff8697f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 20V, Negative-QTOF	splash10-014i-2900000000-fa9a0a108b9af14b772e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 40V, Negative-QTOF	splash10-015c-9300000000-46e0fcc817bf5503d1c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 10V, Positive-QTOF	splash10-016r-1900000000-d412b5d94db1438f385d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 20V, Positive-QTOF	splash10-017l-9500000000-33b7d9c53506ef59566e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 40V, Positive-QTOF	splash10-00kf-9000000000-0469fce624a6b391b90b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 20V, Negative-QTOF	splash10-014j-0900000000-ee150fe3507bd331335a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-p-mentha-1,8-dien-6-one 40V, Negative-QTOF	splash10-014i-9400000000-9a8bbca744087a33ede9	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

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

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

FDB015990

KNApSAcK ID

Not Available

Chemspider ID

337461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

380816

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1596981

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 ]
(). 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 2-Hydroxy-p-mentha-1,8-dien-6-one (HMDB0037012)

MOL for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

3D MOL for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

3D SDF for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

3D-SDF for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

PDB for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

3D PDB for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

SMILES for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

INCHI for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

Structure for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

3D Structure for HMDB0037012 (2-Hydroxy-p-mentha-1,8-dien-6-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra