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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 00:25:24 UTC

Update Date

2021-09-24 00:25:24 UTC

HMDB ID

HMDB0303238

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+/-)-2-Hydroxypiperitone

Description

(+/-)-2-hydroxypiperitone, also known as 2-hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one or barosma camphor, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Thus, (+/-)-2-hydroxypiperitone is considered to be an isoprenoid lipid molecule (+/-)-2-hydroxypiperitone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (+/-)-2-hydroxypiperitone is a blackcurrant, buchu, and leaves tasting compound found in blackcurrant, peppermint, and spearmint, which makes (+/-)-2-hydroxypiperitone a potential biomarker for the consumption of these food products.

Structure

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

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

COMPND    HMDB0303238
HETATM    1  C1  UNL     1       3.601  -0.401   0.061  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.121  -0.313  -0.022  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.529   0.678   0.643  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.282   1.596   1.387  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.073   0.788   0.578  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.482   1.495   1.445  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.608   0.059  -0.497  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.111   0.098  -0.387  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.608  -0.505   0.898  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.653   1.488  -0.566  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.071  -1.331  -0.605  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.404  -1.313  -0.822  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.984  -1.328  -0.397  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.042   0.457  -0.524  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.985  -0.297   1.089  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.634   2.404   0.855  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.351   0.585  -1.458  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.529  -0.520  -1.215  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.232  -0.016   1.796  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.719  -0.376   0.901  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.447  -1.610   0.910  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.859   2.087  -1.089  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.938   1.945   0.409  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.594   1.493  -1.178  1.00  0.00           H  
HETATM   25  H13 UNL     1      -0.376  -1.905   0.293  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.534  -1.791  -1.523  1.00  0.00           H  
HETATM   27  H15 UNL     1       1.823  -2.328  -0.584  1.00  0.00           H  
HETATM   28  H16 UNL     1       1.637  -1.139  -1.898  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   12
CONECT    3    4    5
CONECT    4   16
CONECT    5    6    6    7
CONECT    7    8   11   17
CONECT    8    9   10   18
CONECT    9   19   20   21
CONECT   10   22   23   24
CONECT   11   12   25   26
CONECT   12   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one	ChEBI
2-Hydroxypiperitone	ChEBI
Barosma camphor	ChEBI
Buccocamphor	ChEBI
Buchu camphor	ChEBI

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

2-hydroxy-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one

Traditional Name

diosphenol

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC(C)=C(O)C1=O

InChI Identifier

InChI=1S/C10H16O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h6,8,11H,4-5H2,1-3H3

InChI Key

QSIMLPCPCXVYDD-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
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

enol (CHEBI:4632 )
cyclic monoterpene ketone (CHEBI:4632 )
Menthane monoterpenoids (C09854 )
Cyclic monoterpenes (C09854 )
Menthane monoterpenoids (LMPR0102090061 )

Ontology

Exogenous (HMDB: HMDB0303238)

Food

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)
Spearmint (FooDB: FOOD00112)

Process

Not Available

Role

Biological role

Anti bacterial (HMDB: HMDB0303238)
Anti septic (HMDB: HMDB0303238)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Diuretic (HMDB: HMDB0303238)

Agriculture

Pesticide (HMDB: HMDB0303238)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.34	ALOGPS
logP	2.49	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-3.5	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	49.31 m³·mol⁻¹	ChemAxon
Polarizability	19.24 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
AllCCS	[M+H]+	136.666	32859911
AllCCS	[M+H-H2O]+	132.372	32859911
AllCCS	[M+Na]+	141.82	32859911
AllCCS	[M+NH4]+	140.667	32859911
AllCCS	[M-H]-	140.534	32859911
AllCCS	[M+Na-2H]-	141.854	32859911
AllCCS	[M+HCOO]-	143.379	32859911
DeepCCS	[M+H]+	141.838	30932474
DeepCCS	[M-H]-	138.011	30932474
DeepCCS	[M-2H]-	175.482	30932474
DeepCCS	[M+Na]+	151.093	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-2-Hydroxypiperitone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(C)C)CC1	1581.2	Semi standard non polar	33892256
(+/-)-2-Hydroxypiperitone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(C)C)CC1	1645.9	Standard non polar	33892256
(+/-)-2-Hydroxypiperitone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(C)C)CC1	1601.4	Standard polar	33892256
(+/-)-2-Hydroxypiperitone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	2038.1	Semi standard non polar	33892256
(+/-)-2-Hydroxypiperitone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	2035.7	Standard non polar	33892256
(+/-)-2-Hydroxypiperitone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	1892.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9600000000-70bf25fc900c37d449ab	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 - (+/-)-2-Hydroxypiperitone 10V, Positive-QTOF	splash10-014i-0900000000-1803785e8d1210e797d4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 20V, Positive-QTOF	splash10-0690-9600000000-9f556853f5687a820cc5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 40V, Positive-QTOF	splash10-0a4i-9000000000-55da8d218eb23aa9167e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 10V, Negative-QTOF	splash10-014i-0900000000-160e4f6e35dc7373498d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 20V, Negative-QTOF	splash10-014i-0900000000-2d9d5fb58715b628fb6a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 40V, Negative-QTOF	splash10-0a4j-9600000000-a298434f16f24d551b89	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 10V, Positive-QTOF	splash10-014i-0900000000-a54e4d6642efaad786cd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 20V, Positive-QTOF	splash10-014i-9300000000-b2eb468f0a9851bd5e6d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 40V, Positive-QTOF	splash10-067l-9000000000-8126f24a3677661894ce	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 20V, Negative-QTOF	splash10-014i-0900000000-1dfc89425e0432230af4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-2-Hydroxypiperitone 40V, Negative-QTOF	splash10-01b9-9100000000-252cd44c5e32228779cb	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4632

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021121

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (+/-)-2-Hydroxypiperitone (HMDB0303238)

MOL for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

3D MOL for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

3D SDF for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

3D-SDF for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

PDB for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

3D PDB for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

SMILES for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

INCHI for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

Structure for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

3D Structure for HMDB0303238 ((+/-)-2-Hydroxypiperitone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra