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Showing NP-Card for alpha-Elemol (NP0046888)

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Record Information
Version1.0
Created at2022-03-17 20:31:10 UTC
Updated at2022-03-17 20:31:11 UTC
NP-MRD IDNP0046888
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Elemol
DescriptionAlpha-Elemol, also known as a-elemol, belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. alpha-Elemol is found in Alphinia galanga, Angelica archangelica, Annona reticulata, Artemisia alba, Artemisia annua, Artemisia annua L.cultivar Jwarharti , Artemisia arborescens, Artemisia sericea, Aspergillus candidus, Atractylodes lancea, Baccharis sagittalis, Boswellia papyrifera, Bothriochloa bladhii, Chamaecyparis obtusa, Chimonanthus praecox, Chromolaena odorata, Cinnamomum illicioides, Cinnamomum sieboldii, Cistus albidus, Citrus aurantium, Citrus nobilis, Citrus reticulata , Citrus sinensis, Citrus spp., Cleistopholis patens, Cryptomeria japonica, Cymbopogon citratus, Cymbopogon flexuosus, Cymbopogon nardus, Cymbopogon winterianus, Dictamnus dasycarpus , Entandrophragma cylindricum, Eremophila dalyana, Eremophila flaccida, Eucalyptus gunnii , Eupatorium capillifolium, Fortunella margarita , Gackstroemia magellanica, Guatteriopsis friesiana, Hedychium spicatum, Helichrysum odoratissimum, Helietta apiculata, Heracleum dissectum, Hexalobus monopetalus, Java citronella, Juniperus comitana, Juniperus communis, Juniperus monticola, Juniperus phoenicea , Juniperus taxifolia, Juniperus thurifera, Juniperus thurifera var.africana, Kadsura japonica , Lessingia glandulifera, Lippia rehmannii, Liquidambar styraciflua, Manila elemi, Micromeria biflora, Micromeria sinaica, Monocyclanthus vignei, Murraya exotica , Murraya paniculata , Myrrhis odorata, Ocimum campechianum, Ocimum tenuiflorum , Olearia phlogopappa, Parthenium argentatum, Phebalium squamulosum, Pimpinella anisum, Pinus halepensis , Pinus sibirica, Piper fimbriulatum, Piper guineense, Piper marginatum, Piper ribesioides, Psiadia altissima, Psidium guajava , Psidium guineense, Pulicaria arabica, Ruta angustifolia, Salvia cinnabarina, Salvia sclarea, Santolina chamaecyparissus, Schinus molle, Tanacetum macrophyllum, Uvariopsis tripetala, Valeriana officinalis, Virola surinamensis, Vitex negundo, Xylopia aethiopica, Xylopia aromatica, Xylopia parviflora , Xylopia rubescens, Xylopia sericea and Zanthoxylum simulans. It was first documented in 1986 (PMID: 3765656). Alpha-Elemol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 18640176) (PMID: 20016930) (PMID: 24453926) (PMID: 26035417) (PMID: 26996033) (PMID: 27899302).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046888 (alpha-Elemol)


  Mrv0541 02241221052D          

 16 16  0  0  1  0            999 V2000
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
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3D MOL for NP0046888 (alpha-Elemol)

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3D SDF for NP0046888 (alpha-Elemol)

  Mrv0541 02241221052D          

 16 16  0  0  1  0            999 V2000
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046888

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-7-15(6)9-8-12(14(4,5)16)10-13(15)11(2)3/h7,12-13,16H,1-2,8-10H2,3-6H3/t12-,13+,15-/m1/s1

> <INCHI_KEY>
GFJIQNADMLPFOW-VNHYZAJKSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.407981792743943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]propan-2-ol

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.6914658343333326

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.317389158856518

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9103739819161588

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
70.20779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046888 (alpha-Elemol)
Download
PDB for NP0046888 (alpha-Elemol)
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  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.870   4.937   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15   16                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   12   13                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    9   14                                                       
CONECT   14   13    3                                                       
CONECT   15    2                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0046888 (alpha-Elemol)
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SMILES for NP0046888 (alpha-Elemol)
CC(=C)[C@@H]1C[C@@H](CC[C@@]1(C)C=C)C(C)(C)O
Download
INCHI for NP0046888 (alpha-Elemol)
InChI=1S/C15H26O/c1-7-15(6)9-8-12(14(4,5)16)10-13(15)11(2)3/h7,12-13,16H,1-2,8-10H2,3-6H3/t12-,13+,15-/m1/s1
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View in JSmol
Synonyms
ValueSource
(1R,3S,4S)-4-Ethenyl-alpha,alpha,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolChEBI
(1S,2S,4R)-(-)-alpha,alpha-Dimethyl-1-vinyl-O-menth-8-ene-4-methanolChEBI
1R,1alpha,3alpha,4beta-4-Ethenyl-alpha,alpha,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolChEBI
(1R,3S,4S)-4-Ethenyl-a,a,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolGenerator
(1R,3S,4S)-4-Ethenyl-α,α,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolGenerator
(1S,2S,4R)-(-)-a,a-Dimethyl-1-vinyl-O-menth-8-ene-4-methanolGenerator
(1S,2S,4R)-(-)-Α,α-dimethyl-1-vinyl-O-menth-8-ene-4-methanolGenerator
1R,1a,3a,4b-4-Ethenyl-a,a,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolGenerator
1R,1Α,3α,4β-4-ethenyl-α,α,4-trimethyl-3-(1-methylethenyl)cyclohexanemethanolGenerator
a-ElemolGenerator
Α-elemolGenerator
Elemol, (1R-(1alpha,3beta,4beta))-isomerMeSH
Chemical FormulaC15H26O
Average Mass222.3663 Da
Monoisotopic Mass222.19837 Da
IUPAC Name2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]propan-2-ol
Traditional Name2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]propan-2-ol
CAS Registry Number639-99-6
SMILES
CC(=C)[C@@H]1C[C@@H](CC[C@@]1(C)C=C)C(C)(C)O
InChI Identifier
InChI=1S/C15H26O/c1-7-15(6)9-8-12(14(4,5)16)10-13(15)11(2)3/h7,12-13,16H,1-2,8-10H2,3-6H3/t12-,13+,15-/m1/s1
InChI KeyGFJIQNADMLPFOW-VNHYZAJKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alphinia galanga-
Angelica archangelicaLOTUS Database
Annona reticulataLOTUS Database
Apium graveolensFooDB
Artemisia albaLOTUS Database
Artemisia annuaLOTUS Database
Artemisia annua L.cultivar JwarhartiPlant
Artemisia arborescensLOTUS Database
Artemisia sericeaLOTUS Database
Aspergillus candidusLOTUS Database
Atractylodes lanceaLOTUS Database
Baccharis sagittalisLOTUS Database
Boswellia papyriferaLOTUS Database
Bothriochloa bladhiiLOTUS Database
Chamaecyparis obtusaLOTUS Database
Chimonanthus praecoxLOTUS Database
Chromolaena odorataLOTUS Database
Cinnamomum illicioidesPlant
Cinnamomum sieboldiiLOTUS Database
Cistus albidusLOTUS Database
Citrus aurantiumLOTUS Database
Citrus nobilisLOTUS Database
Citrus reticulataPlant
Citrus sinensisLOTUS Database
Citrus spp.Plant
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cleistopholis patensLOTUS Database
Coriandrum sativum L.FooDB
Cryptomeria japonicaPlant
Cymbopogon citratusLOTUS Database
Cymbopogon flexuosusLOTUS Database
Cymbopogon nardusLOTUS Database
Cymbopogon winterianusLOTUS Database
Dictamnus dasycarpusPlant
Entandrophragma cylindricumLOTUS Database
Eremophila dalyanaLOTUS Database
Eremophila flaccidaLOTUS Database
Eucalyptus gunniiPlant
Eupatorium capillifoliumLOTUS Database
Fortunella margaritaPlant
Gackstroemia magellanica-
Ginkgo bilobaFooDB
Guatteria friesianaPlant
Hedychium spicatumLOTUS Database
Helichrysum odoratissimumLOTUS Database
Helietta apiculataLOTUS Database
Heracleum dissectumLOTUS Database
Hexalobus monopetalusLOTUS Database
Hyssopus officinalis L.FooDB
Java citronella-
Juniperus comitanaLOTUS Database
Juniperus communisLOTUS Database
Juniperus monticolaLOTUS Database
Juniperus phoeniceaPlant
Juniperus taxifoliaLOTUS Database
Juniperus thuriferaLOTUS Database
Juniperus thurifera var.africanaPlant
Kadsura japonicaPlant
Lessingia glanduliferaLOTUS Database
Lippia rehmanniiLOTUS Database
Liquidambar styracifluaLOTUS Database
Manila elemi-
Mentha aquaticaFooDB
Mentha spicataFooDB
Micromeria bifloraLOTUS Database
Micromeria sinaicaLOTUS Database
Monocyclanthus vigneiLOTUS Database
Murraya exoticaPlant
Murraya paniculataPlant
Myrrhis odorataLOTUS Database
Ocimum basilicumFooDB
Ocimum campechianumLOTUS Database
Ocimum tenuiflorumPlant
Olearia phlogopappaLOTUS Database
Origanum onitesFooDB
Origanum vulgareFooDB
Parthenium argentatumLOTUS Database
Phebalium squamulosumLOTUS Database
Pimpinella anisumLOTUS Database
Pinus halepensisPlant
Pinus sibiricaPlant
Piper fimbriulatumPlant
Piper guineenseLOTUS Database
Piper marginatumLOTUS Database
Piper nigrum L.FooDB
Piper ribesioidesLOTUS Database
Psiadia altissimaLOTUS Database
Psidium guajavaPlant
Psidium guineenseLOTUS Database
Pulicaria arabicaLOTUS Database
Ruta angustifoliaLOTUS Database
Salvia cinnabarinaLOTUS Database
Salvia rosmarinusFooDB
Salvia sclareaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Schinus molleLOTUS Database
Tanacetum macrophyllumPlant
Uvariopsis tripetalaLOTUS Database
Valeriana officinalisLOTUS Database
Virola surinamensisLOTUS Database
Vitex negundoLOTUS Database
Xylopia aethiopicaLOTUS Database
Xylopia aromaticaLOTUS Database
Xylopia parvifloraPlant
Xylopia rubescensPlant
Xylopia sericeaPlant
Zanthoxylum simulansLOTUS Database
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentElemane sesquiterpenoids  
Alternative Parents
Substituents
  • Elemane sesquiterpenoid
    • 

  • Tertiary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP3.78ALOGPS
logP3.69ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.32ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.21 m³·mol⁻¹ChemAxon
Polarizability27.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006367  
KNApSAcK IDC00012005  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92138  
PDB IDNot Available
ChEBI ID141221  
Good Scents IDNot Available
References
General References
  1. Bhatia SP, Letizia CS, Api AM: Fragrance material review on elemol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S147-8. doi: 10.1016/j.fct.2008.06.045. Epub 2008 Jul 2. [PubMed:18640176  ] 
  2. Carroll JF, Paluch G, Coats J, Kramer M: Elemol and amyris oil repel the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays. Exp Appl Acarol. 2010 Aug;51(4):383-92. doi: 10.1007/s10493-009-9329-0. Epub 2009 Dec 18. [PubMed:20016930  ] 
  3. Odimegwu JI, Odukoya O, Yadav RK, Chanotiya CS, Ogbonnia S, Sangwan NS: A new source of elemol rich essential oil and existence of multicellular oil glands in leaves of the Dioscorea species. ScientificWorldJournal. 2013 Dec 23;2013:943598. doi: 10.1155/2013/943598. eCollection 2013. [PubMed:24453926  ] 
  4. Yang H, Jung EM, Ahn C, Lee GS, Lee SY, Kim SH, Choi IG, Park MJ, Lee SS, Choi DH, Jeung EB: Elemol from Chamaecyparis obtusa ameliorates 2,4-dinitrochlorobenzene-induced atopic dermatitis. Int J Mol Med. 2015 Aug;36(2):463-72. doi: 10.3892/ijmm.2015.2228. Epub 2015 May  29. [PubMed:26035417  ] 
  5. Casiglia S, Bruno M, Senatore F, Senatore F: Chemical Composition of the Essential Oil of Bupleurum fontanesii (Apiaceae) Growing Wild in Sicily and its Activity on Microorganisms Affecting Historical Art Crafts. Nat Prod Commun. 2016 Jan;11(1):105-8. [PubMed:26996033  ] 
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