Showing Compound (+/-)-2-Hydroxypiperitone (FDB009611)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:43 UTC

Update date

2019-11-26 03:03:29 UTC

Primary ID

FDB009611

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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.

CAS Number

490-03-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one	ChEBI
2-Hydroxypiperitone	ChEBI
Barosma camphor	ChEBI
Buccocamphor	ChEBI
Buchu camphor	ChEBI
2-Cyclohexen-1-one, 2-hydroxy-3-methyl-6-(1-methylethyl)-	biospider
2-hydroxy-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one	biospider
2-Hydroxy-6-(isopropyl)-3-methylcyclohex-2-en-1-one	biospider
Diosphenol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	4.71 g/L	ALOGPS
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

Chemical Formula

C10H16O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

Classification

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

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	83 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004l-9600000000-70bf25fc900c37d449ab	2015-03-01	View Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-1803785e8d1210e797d4	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0690-9600000000-9f556853f5687a820cc5	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-55da8d218eb23aa9167e	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-160e4f6e35dc7373498d	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-2d9d5fb58715b628fb6a	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4j-9600000000-a298434f16f24d551b89	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-a54e4d6642efaad786cd	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9300000000-b2eb468f0a9851bd5e6d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067l-9000000000-8126f24a3677661894ce	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-cb7592114e600c180aec	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-1dfc89425e0432230af4	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-9100000000-252cd44c5e32228779cb	2021-10-21	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

1780

Dr. Duke ID

DIOSPHENOL

BIGG ID

Not Available

KNApSAcK ID

C00003042

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1021121

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
minty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buchu	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leaves	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
blackcurrant	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.