ChemFOnt: Showing chemical card for (+/-)-2-Hydroxypiperitone (CFc000282754)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:24 UTC

Chemfont ID

CFc000282754

Molecule Identification

Common Name

(+/-)-2-Hydroxypiperitone

Definition

(+/-)-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 SDF PDB SMILES InChI

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

490-03-9

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 )

Functional 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

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

External Links

HMDB ID

HMDB0303238

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

References

Synthesis Reference

Not Available

Showing chemical card for (+/-)-2-Hydroxypiperitone (CFc000282754)

MOL for CFc000282754 ((+/-)-2-Hydroxypiperitone)

3D MOL for CFc000282754 ((+/-)-2-Hydroxypiperitone)

3D SDF for CFc000282754 ((+/-)-2-Hydroxypiperitone)

3D-SDF for CFc000282754 ((+/-)-2-Hydroxypiperitone)

PDB for CFc000282754 ((+/-)-2-Hydroxypiperitone)

3D PDB for CFc000282754 ((+/-)-2-Hydroxypiperitone)

SMILES for CFc000282754 ((+/-)-2-Hydroxypiperitone)

INCHI for CFc000282754 ((+/-)-2-Hydroxypiperitone)

Structure for CFc000282754 ((+/-)-2-Hydroxypiperitone)

3D Structure for CFc000282754 ((+/-)-2-Hydroxypiperitone)