NP-MRD: Showing NP-Card for (+)-Menthyl acetate (NP0046820)

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Record Information

Version

2.0

Created at

2022-03-17 20:30:03 UTC

Updated at

2022-03-17 20:30:03 UTC

NP-MRD ID

NP0046820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Menthyl acetate

Description

(±)-Menthyl acetate 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 (±)-Menthyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-Menthyl acetate has been detected, but not quantified in, cornmints. (+)-Menthyl acetate is found in Agathosma betulina, Cryptomeria japonica, Hesperozygis rhododon, Lepechinia chamaedryoides, Matricaria chamomilla, Mentha piperita, Mentha canadensis, Mentha verticillata, Minthostachys mollis, Origanum cordifolium, Platostoma africanum, Polygala senega, Senna alexandrina, Thapsia villosa and Vanilla planifolia. This could make (±)-menthyl acetate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212462D          

 14 14  0  0  0  0            999 V2000
   -3.3463   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6318   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -1.4438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3463   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0607   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0607   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0607   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  3 13  1  6  0  0  0
  4  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m0/s1

> <INCHI_KEY>
XHXUANMFYXWVNG-WCQGTBRESA-N

> <FORMULA>
C12H22O2

> <MOLECULAR_WEIGHT>
198.3019

> <EXACT_MASS>
198.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.74249896331213

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.1053985573333325

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003223453074533

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.5968

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0      -6.246  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.913  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.913  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.246  -3.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.580  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.580  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.246   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.246  -5.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.580  -5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.913  -5.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.912  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.245  -2.695   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.579  -3.465   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.245  -1.155   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12                                                            
CONECT   12   11   13   14                                                  
CONECT   13    3   12                                                       
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(±)-menthyl acetic acid	Generator
(+-)-Menthol acetate	HMDB
(+-)-Menthyl acetate	HMDB
(+/-)-menthyl acetate	HMDB
(DL)-Menthyl acetate	HMDB
DL-p-Menth-3-yl acetate	HMDB
Menthol acetate	HMDB
Menthyl acetate	HMDB
(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid	Generator
(+)-Menthyl acetic acid	Generator

Chemical Formula

C₁₂H₂₂O₂

Average Mass

198.3019 Da

Monoisotopic Mass

198.16198 Da

IUPAC Name

(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl acetate

Traditional Name

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl acetate

CAS Registry Number

89-48-5

SMILES

CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m0/s1

InChI Key

XHXUANMFYXWVNG-WCQGTBRESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agathosma betulina	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Hesperozygis rhododon	LOTUS Database	35616633
Lepechinia chamaedryoides	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Mentha arvensis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha piperita	LOTUS Database	35616633
Mentha sachalinensis	LOTUS Database	35616633
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha verticillata	LOTUS Database	35616633
Minthostachys mollis	LOTUS Database	35616633
Origanum cordifolium	LOTUS Database	35616633
Platostoma africanum	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Thapsia villosa	LOTUS Database	35616633
Vanilla planifolia Jacks.	LOTUS Database	35616633
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.54	ALOGPS
logP	3.11	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.6 m³·mol⁻¹	ChemAxon
Polarizability	23.74 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

HMDB0041264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006041

KNApSAcK ID

Not Available

Chemspider ID

191402

KEGG Compound ID

C09870

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

220674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Menthyl acetate (NP0046820)

MOL for NP0046820 ((+)-Menthyl acetate)

3D MOL for NP0046820 ((+)-Menthyl acetate)

3D SDF for NP0046820 ((+)-Menthyl acetate)

3D-SDF for NP0046820 ((+)-Menthyl acetate)

PDB for NP0046820 ((+)-Menthyl acetate)

3D PDB for NP0046820 ((+)-Menthyl acetate)

SMILES for NP0046820 ((+)-Menthyl acetate)

INCHI for NP0046820 ((+)-Menthyl acetate)

Structure for NP0046820 ((+)-Menthyl acetate)

3D Structure for NP0046820 ((+)-Menthyl acetate)