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Showing NP-Card for Neryl acetate (NP0048451)

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Record Information
Version2.0
Created at2022-03-17 20:56:41 UTC
Updated at2022-03-17 20:56:41 UTC
NP-MRD IDNP0048451
Secondary Accession NumbersNone
Natural Product Identification
Common NameNeryl acetate
DescriptionGeranyl acetate, also known as neryl ethanoate or fema 2509, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Geranyl acetate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranyl acetate is a blossom, citrus, and dewy tasting compound. Outside of the human body, Geranyl acetate is found, on average, in the highest concentration within a few different foods, such as spearmints, lemons, and limes and in a lower concentration in sweet oranges and mandarin orange (clementine, tangerine). Geranyl acetate has also been detected, but not quantified in, several different foods, such as pepper (spice), sweet basils, common persimmons, mango, and nutmegs. This could make geranyl acetate a potential biomarker for the consumption of these foods. Geranyl acetate is a potentially toxic compound. Neryl acetate is found in Agathosma betulina, Aloysia citrodora, Alphinia galanga, Alpinia conchigera, Alpinia galanga, Artemisia absinthium, Asarum canadense, Aspalathus linearis, Baccharis aliena, Baccharis dracunculifolia, Bahia ambrosioides, Bellis perennis, Boswellia sacra, Callistemon linearis, Cananga odorata , Citrus aurantium , Citrus iyo, Citrus latifolia , Citrus grandis , Citrus medica , Citrus reticulate x Citrus sinensis, Citrus sinensis, Citrus sinensis L. , Citrus vulgaris , Clinopodium grandiflorum, Conyza newii , Coriandrum sativum, Curcuma longa , Cymbopogon martinii , Daphne odora, Daucus carota, Elsholtzia ciliata, Elsholtzia pilosa, Eucalyptus macarthurii, Eupatorium cannabinum, Eupatorium capillifolium, Eupatorium fortunei , Helichrysum amorginum, Helichrysum italicum , Houttuynia cordata , Houttuynia emeiensis, Juniperus communis, Juniperus taxifolia, Lavandin abrialis, Lavandula angustifolia , Lepechinia chamaedryoides, Leptospermum scoparium , Mentha piperita L. , Myrtus communis , Pandanus tectorius, Pectis elongata, Pelargonium graveolens , Pelargonium odoratissimum , Pelargonium quercifolium, Persea americana, Petasites albus , Phagnalon sordidum, Pinus sibirica, Piper aduncum, Poncirus trifoliate x Citrus sinensis, Prunus armeniaca L. (K33-81) , Rosa gallica, Salvia fruticosa, Salvia sclarea, Saxifraga stolonifera Meerb. , Sideritis tragoriganum, Brassica hirta , Stoebe vulgaris, Syzygium nervosum, Tanacetum longifolium, Tanacetum macrophyllum, Teucrium polium, Zanthoxylum simulans and Zingiber officinale . Neryl acetate was first documented in 2011 (PMID: 21854172). Found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries (PMID: 25675145) (PMID: 23495152) (PMID: 26439817) (PMID: 27794602).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048451 (Neryl acetate)


  Mrv0541 02241215152D          

 14 13  0  0  0  0            999 V2000
    2.1436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.8563    0.0000 C   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
  2  4  2  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
  7  8  1  0  0  0  0
  7  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  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for NP0048451 (Neryl acetate)

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3D SDF for NP0048451 (Neryl acetate)

  Mrv0541 02241215152D          

 14 13  0  0  0  0            999 V2000
    2.1436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.8563    0.0000 C   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
  2  4  2  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
  7  8  1  0  0  0  0
  7  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  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C/COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8-

> <INCHI_KEY>
HIGQPQRQIQDZMP-FLIBITNWSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.65733263908416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl acetate

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
2.9435087063333336

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004434726067085

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.333600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neryl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048451 (Neryl acetate)
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PDB for NP0048451 (Neryl acetate)
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       4.001   3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.334   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.335   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.335   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.335   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -1.155   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -2.695   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.334  -3.465   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   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   26    0
END

Download
3D PDB for NP0048451 (Neryl acetate)
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SMILES for NP0048451 (Neryl acetate)
CC(C)=CCC\C(C)=C/COC(C)=O
Download
INCHI for NP0048451 (Neryl acetate)
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8-
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View in JSmol
Synonyms
ValueSource
(2Z)-3,7-Dimethyl-2,6-octadienyl acetateChEBI
cis-3,7-Dimethyl-2,6-octadien-1-ol acetateChEBI
cis-Geranyl acetateChEBI
Neryl ethanoateChEBI
(2Z)-3,7-Dimethyl-2,6-octadienyl acetic acidGenerator
cis-3,7-Dimethyl-2,6-octadien-1-ol acetic acidGenerator
cis-Geranyl acetic acidGenerator
Neryl ethanoic acidGenerator
Geranyl acetic acidGenerator
(2E)-3,7-Dimethyl-2,6-octadienyl acetateHMDB
(2E)-3,7-Dimethylocta-2,6-dien-1-yl acetateHMDB
(e)-3,7-Dimethyl-2,6-octadien-1-yl acetateHMDB
(Z)-3,7-Dimethyl-2,6-octadienyl acetateHMDB
1,6-Octadiene, 7-methyl-3-methylene-, acetylatedHMDB
1-Octanol, 3,7-dimethyl-, 1-acetate, tetradehydro deriv.HMDB
1-Octanol, 3,7-dimethyl-, acetate, tetradehydro deriv.HMDB
2,6-Dimethyl-2,6-octadiene-8-yl acetateHMDB
2,6-Octadien-1-ol, 3,7-dimethyl-, acetateHMDB
3,7-Dimethyl-1-acetate(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-1-acetate(2Z)-2,6-octadien-1-olHMDB
3,7-Dimethyl-2,6-octadien-1-ol acetateHMDB
3,7-Dimethyl-acetate(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-acetate(2Z)-2,6-octadien-1-olHMDB
3,7-Dimethyl-acetate(e)-2,6-octadien-1-olHMDB
3,7-Dimethyl-acetatetrans-2,6-octadien-1-olHMDB
3,7-Dimethyloctyl acetate, tetradehydro derivativeHMDB
Acetic acid, geraniol esterHMDB
Acetic acid, geranyl esterHMDB
cis-3,7-Dimethyl-2,6-octadien-1-yl acetateHMDB
cis-3,7-Dimethyl-2,6-octadien-1-yl ethanoateHMDB
FEMA 2509HMDB
Geranyl acetate aHMDB
Geranyl ethanoateHMDB
MeraneineHMDB
Nerol acetate (6ci)HMDB
trans-2,6-Dimethyl-2,6-octadien-8-yl ethanoateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl acetateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl ethanoateHMDB
trans-3,7-Dimethyl-2,6-octadienyl acetateHMDB
trans-Geraniol acetateHMDB
trans-Geranyl acetateHMDB
Nerol acetateHMDB
Geraniol acetate, (Z)-isomerHMDB
Geraniol acetateHMDB
Geraniol acetate, (e)-isomerHMDB
3,7-Dimethyl-2Z,6-octadienyl acetic acidGenerator
Geranyl acetateMeSH
Neryl acetateMeSH
Neryl acetic acidGenerator
Chemical FormulaC12H20O2
Average Mass196.2860 Da
Monoisotopic Mass196.14633 Da
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl acetate
Traditional Nameneryl acetate
CAS Registry Number105-87-3
SMILES
CC(C)=CCC\C(C)=C/COC(C)=O
InChI Identifier
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8-
InChI KeyHIGQPQRQIQDZMP-FLIBITNWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Aloysia citrodoraLOTUS Database
Alphinia galanga-
Alpinia conchigeraLOTUS Database
Alpinia galangaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Artemisia absinthiumLOTUS Database
Artemisia vulgarisFooDB
Asarum canadenseLOTUS Database
Aspalathus linearisLOTUS Database
Baccharis alienaLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Bahia ambrosioidesLOTUS Database
Bellis perennisLOTUS Database
Boswellia sacraLOTUS Database
Callistemon linearisLOTUS Database
Cananga odorataPlant
Citrus aurantiifoliaFooDB
Citrus aurantiumPlant
Citrus iyoLOTUS Database
Citrus latifoliaPlant
Citrus limonFooDB
Citrus maximaPlant
Citrus medicaPlant
Citrus reticulataFooDB
Citrus reticulate x Citrus sinensisPlant
Citrus sinensisLOTUS Database
Citrus sinensis L.Plant
Citrus vulgarisPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clinopodium grandiflorumLOTUS Database
Conyza newiiPlant
Coriandrum sativumLOTUS Database
Coriandrum sativum L.FooDB
Curcuma longaPlant
Cymbopogon martiniiPlant
Daphne odoraLOTUS Database
Daucus carotaLOTUS Database
Diospyros virginianaFooDB
Elettaria cardamomumFooDB
Elsholtzia ciliataLOTUS Database
Elsholtzia pilosaLOTUS Database
Eucalyptus macarthuriiPlant
Eupatorium cannabinumLOTUS Database
Eupatorium capillifoliumLOTUS Database
Eupatorium fortuneiPlant
Helichrysum amorginumLOTUS Database
Helichrysum italicumPlant
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Juniperus communisLOTUS Database
Juniperus taxifoliaLOTUS Database
Laurus nobilis L.FooDB
Lavandin abrialis-
Lavandula angustifoliaPlant
Lepechinia chamaedryoidesLOTUS Database
Leptospermum scopariumPlant
Mangifera indicaFooDB
Melissa officinalis L.FooDB
Mentha piperita L.Plant
Mentha spicataFooDB
Myristica fragransFooDB
Myrtus communisPlant
Ocimum basilicumFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Pandanus tectoriusLOTUS Database
Pectis elongataLOTUS Database
Pelargonium graveolensPlant
Pelargonium odoratissimumPlant
Pelargonium quercifoliumLOTUS Database
Persea americanaLOTUS Database
Petasites albusPlant
Phagnalon sordidumPlant
Pinus sibiricaPlant
Piper aduncumLOTUS Database
Piper nigrum L.FooDB
Poncirus trifoliate x Citrus sinensisPlant
Prunus armeniaca L. (K33-81)Plant
Rosa gallicaLOTUS Database
Salvia fruticosaLOTUS Database
Salvia sclareaLOTUS Database
Saxifraga stolonifera Meerb.Plant
Sideritis tragoriganumLOTUS Database
Sinapis albaPlant
Stoebe vulgarisLOTUS Database
Syzygium nervosumLOTUS Database
Tanacetum longifoliumPlant
Tanacetum macrophyllumPlant
Teucrium poliumLOTUS Database
Zanthoxylum simulansLOTUS Database
Zingiber officinalePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohol esters  
Direct ParentFatty alcohol esters  
Alternative Parents
Substituents
  • Fatty alcohol ester
    • 

  • Monoterpenoid
    • 

  • Acyclic monoterpenoid
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP4.11ALOGPS
logP2.94ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.33 m³·mol⁻¹ChemAxon
Polarizability23.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035157  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014946  
KNApSAcK IDC00035138  
Chemspider ID1266018  
KEGG Compound IDC09861  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeryl_acetate  
METLIN IDNot Available
PubChem Compound1549025  
PDB IDNot Available
ChEBI ID141210  
Good Scents IDNot Available
References
General References
  1. Zeljkovic SC, Solic ME, Maksimovic M: Volatiles of Helichrysum italicum (Roth) G. Don from Croatia. Nat Prod Res. 2015;29(19):1874-7. doi: 10.1080/14786419.2015.1009458. Epub 2015 Feb 12. [PubMed:25675145  ] 
  2. Guleria S, Saini R, Jaitak V, Kaul VK, Lal B, Rahi P, Gulati A, Singh B: Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas. Nat Prod Res. 2011 Aug;25(13):1250-60. doi: 10.1080/14786419.2011.557375. [PubMed:21854172  ] 
  3. Leonardi M, Ambryszewska KE, Melai B, Flamini G, Cioni PL, Parri F, Pistelli L: Essential-oil composition of Helichrysum italicum (ROTH) G.DON ssp. italicum from Elba Island (Tuscany, Italy). Chem Biodivers. 2013 Mar;10(3):343-55. doi: 10.1002/cbdv.201200222. [PubMed:23495152  ] 
  4. Judzentiene A, Garjonyte R, Budiene J: Variability, toxicity, and antioxidant activity of Eupatorium cannabinum (hemp agrimony) essential oils. Pharm Biol. 2016;54(6):945-53. doi: 10.3109/13880209.2015.1078384. Epub 2015 Oct  6. [PubMed:26439817  ] 
  5. Elsharif SA, Buettner A: Structure-Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives. J Agric Food Chem. 2018 Mar 14;66(10):2324-2333. doi: 10.1021/acs.jafc.6b04534. Epub 2016 Nov 7. [PubMed:27794602  ]