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Showing NP-Card for terpineols (NP0237132)

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Record Information
Version2.0
Created at2022-09-06 20:11:24 UTC
Updated at2022-09-06 20:11:25 UTC
NP-MRD IDNP0237132
Secondary Accession NumbersNone
Natural Product Identification
Common Nameterpineols
DescriptionBeta-Terpineol, also known as p-menth-8-en-1-ol or β-terpineol, 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. Beta-Terpineol is an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-Terpineol is an earthy, must, and pungent tasting compound. Outside of the human body, beta-Terpineol is found, on average, in the highest concentration within a few different foods, such as common thymes, limes, and mandarin orange (clementine, tangerine) and in a lower concentration in pot marjorams. Beta-Terpineol has also been detected, but not quantified in, several different foods, such as cardamoms, nutmegs, cloves, herbs and spices, and dills. terpineols is found in Abies sibirica, Agathosma betulina, Artemisia arborescens, Artemisia herba-alba, Asarum megacalyx, Asarum simile, Aspalathus linearis, Atalantia buxifolia, Cannabis sativa, Cistus creticus, Citrus aurantiifolia, Citrus iyo, Citrus limon, Citrus sinensis, Cryptomeria japonica, Ephedra sinica, Helichrysum italicum, Lavandula stoechas, Liquidambar styraciflua, Pistacia integerrima, Santolina chamaecyparissus, Satureja cuneifolia, Thymus fedtschenkoi, Thymus revolutus, Thymus vulgaris, Vitex agnus-castus and Zingiber mioga. terpineols was first documented in 2006 (PMID: 16714091). This could make beta-terpineol a potential biomarker for the consumption of these foods (PMID: 18640203) (PMID: 23678820).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0237132 (terpineols)


  Mrv0541 02241218402D          

 11 11  0  0  0  0            999 V2000
   -4.5670   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -3.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -3.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -3.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795   -0.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545   -0.0810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
Download

3D MOL for NP0237132 (terpineols)

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.0050   -0.9552    0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    0.1793    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079    1.4352   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8540    0.2343    0.3828 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1978    0.7881   -0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814    0.7088   -0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -0.3873   -0.1531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1470    0.1683    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.3070   -1.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431   -1.2005    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -1.1532    0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759   -1.8820    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -0.9685   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    2.3092    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517    1.5640   -1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736    1.4103    0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    0.8967    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364    0.2599   -1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    1.8488   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    1.7145   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    0.6845   -1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8658   -0.6267    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    0.8659   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967    0.7408    1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717   -0.8111   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112   -2.2856    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -0.8732    1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -1.6189    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639   -1.7393   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  1  0
 11  4  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0237132 (terpineols)


  Mrv0541 02241218402D          

 11 11  0  0  0  0            999 V2000
   -4.5670   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -3.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -3.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814   -3.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795   -0.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545   -0.0810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237132

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h9,11H,1,4-7H2,2-3H3

> <INCHI_KEY>
RUJPNZNXGCHGID-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.80209736960398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.2322311779999997

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.002116372471004

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0482742986811822

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.389399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-terpineol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0237132 (terpineols)

Download
PDB for NP0237132 (terpineols)
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      -8.525  -1.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.859  -2.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.859  -3.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.525  -4.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.191  -3.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.191  -2.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.525  -6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.191  -6.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.859  -6.875   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.295  -0.151   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.755  -0.151   0.000  0.00  0.00           O+0
CONECT    1    2    6   10   11                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0237132 (terpineols)
Download
SMILES for NP0237132 (terpineols)
CC(=C)C1CCC(C)(O)CC1
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INCHI for NP0237132 (terpineols)
InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h9,11H,1,4-7H2,2-3H3
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Synonyms
ValueSource
1-Methyl-4-(1-methylethenyl)cyclohexanolChEBI
1-Methyl-4-(1-methylvinyl)cyclohexan-1-olChEBI
1-Methyl-4-isopropenylcyclohexan-1-olChEBI
4-Isopropenyl-1-methyl-1-cyclohexanolChEBI
p-Menth-8-en-1-olChEBI
b-TerpineolGenerator
Β-terpineolGenerator
1-Methyl-4-(1-methylethenyl)-cyclohexanolHMDB
4-Isopropenyl-1-methylcyclohexanolHMDB
beta -TerpineolHMDB
FEMA 3564HMDB
beta-TerpinolMeSH
1-Methyl-4-(1-methylethenyl)cyclohexanalMeSH
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol
Traditional Nameβ-terpineol
CAS Registry NumberNot Available
SMILES
CC(=C)C1CCC(C)(O)CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h9,11H,1,4-7H2,2-3H3
InChI KeyRUJPNZNXGCHGID-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies sibiricaLOTUS Database
Agathosma betulinaLOTUS Database
Artemisia arborescensLOTUS Database
Artemisia herba-albaLOTUS Database
Asarum megacalyxLOTUS Database
Asarum simileLOTUS Database
Aspalathus linearisLOTUS Database
Atalantia buxifoliaLOTUS Database
Cannabis sativaLOTUS Database
Cistus creticusLOTUS Database
Citrus aurantiifoliaLOTUS Database
Citrus iyoLOTUS Database
Citrus limonLOTUS Database
Citrus sinensisLOTUS Database
Cryptomeria japonicaLOTUS Database
Ephedra sinicaLOTUS Database
Helichrysum italicumLOTUS Database
Lavandula stoechasLOTUS Database
Liquidambar styracifluaLOTUS Database
Pistacia integerrimaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Satureja cuneifoliaLOTUS Database
Thymus fedtschenkoiLOTUS Database
Thymus revolutusLOTUS Database
Thymus vulgarisLOTUS Database
Vitex agnus-castusLOTUS Database
Zingiber miogaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMenthane monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
    • 

  • Monocyclic monoterpenoid
    • 

  • Cyclohexanol
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.73ALOGPS
logP2.23ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)19ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.39 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036996  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015970  
KNApSAcK IDC00048331  
Chemspider ID8418  
KEGG Compound IDC17517  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerpineol  
METLIN IDNot Available
PubChem Compound8748  
PDB IDNot Available
ChEBI ID132899  
Good Scents IDNot Available
References
General References
  1. George V, Mathew J, Sabulal B, Dan M, Shiburaj S: Chemical composition and antimicrobial activity of essential oil from the rhizomes of Amomum cannicarpum. Fitoterapia. 2006 Jul;77(5):392-4. doi: 10.1016/j.fitote.2006.04.003. Epub 2006  May 22. [PubMed:16714091  ] 
  2. Bhatia SP, McGinty D, Letizia CS, Api AM: Fragrance material review on p-menth-8-en-1-ol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S206-8. doi: 10.1016/j.fct.2008.06.070.  Epub 2008 Jul 2. [PubMed:18640203  ] 
  3. Troncoso C, Perez C, Hernandez V, Sanchez-Olate M, Rios D, San Martin A, Becerra J: Induction of defensive response in Eucalyptus globulus plants and its persistence in vegetative propagation. Nat Prod Commun. 2013 Mar;8(3):397-400. [PubMed:23678820  ] 
  4. LOTUS database [Link]