NP-MRD: Showing NP-Card for (±)-p-Mentha-1,8-dien-10-yl acetate (NP0048671)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:20 UTC

Updated at

2022-03-17 21:00:20 UTC

NP-MRD ID

NP0048671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-p-Mentha-1,8-dien-10-yl acetate

Description

(S)-p-Mentha-1,8-dien-10-yl 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 (S)-p-Mentha-1,8-dien-10-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-p-Mentha-1,8-dien-10-yl acetate is a mild, sweet, and fruity tasting compound. Outside of the human body, (S)-p-Mentha-1,8-dien-10-yl acetate has been detected, but not quantified in, a few different foods, such as citrus, fats and oils, and lemons. (±)-p-Mentha-1,8-dien-10-yl acetate is found in Mentha aquatica. This could make (S)-p-mentha-1,8-dien-10-yl acetate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216502D          

 14 14  0  0  0  0            999 V2000
   -1.7852    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -2.2661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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>
NP0048671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(=C)C1CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-9-4-6-12(7-5-9)10(2)8-14-11(3)13/h4,12H,2,5-8H2,1,3H3

> <INCHI_KEY>
BCTDJPZNMXPMIA-UHFFFAOYSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.2701

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.76082488035839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-yl acetate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
2.3801669053333336

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0050132972227575

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.40650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-yl 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      -3.332   1.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.332   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.998  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.664   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.664   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.998   2.694   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.998   4.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.332  -2.696   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.998  -1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.664  -2.696   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.667  -1.924   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.001  -2.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.332  -1.919   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.003  -4.230   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(S)-p-Mentha-1,8-dien-10-yl acetic acid	Generator
2-(4-Methylcyclohex-3-en-1-yl)prop-2-en-1-yl acetic acid	Generator
(±)-p-mentha-1,8-dien-10-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₈O₂

Average Mass

194.2701 Da

Monoisotopic Mass

194.13068 Da

IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-yl acetate

Traditional Name

2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-yl acetate

CAS Registry Number

15111-97-4

SMILES

CC(=O)OCC(=C)C1CCC(C)=CC1

InChI Identifier

InChI=1S/C12H18O2/c1-9-4-6-12(7-5-9)10(2)8-14-11(3)13/h4,12H,2,5-8H2,1,3H3

InChI Key

BCTDJPZNMXPMIA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha aquatica	LOTUS Database	35616633

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	3.65	ALOGPS
logP	2.38	ChemAxon
logS	-2.8	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	4	ChemAxon
Refractivity	57.41 m³·mol⁻¹	ChemAxon
Polarizability	22.76 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

HMDB0037018

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015996

KNApSAcK ID

Not Available

Chemspider ID

55668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61781

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (±)-p-Mentha-1,8-dien-10-yl acetate (NP0048671)

MOL for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

3D MOL for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

3D SDF for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

3D-SDF for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

PDB for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

3D PDB for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

SMILES for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

INCHI for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

Structure for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)

3D Structure for NP0048671 ((±)-p-Mentha-1,8-dien-10-yl acetate)