Record Information
Version1.0
Created at2020-03-19 00:39:25 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000483
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-nerolidol
DescriptionNerolidol also known as peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Nerolidol is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is present in neroli, ginger, jasmine, lavender, tea tree, and lemon grass, and is a dominant scent compound in Brassavola nodosa. Nerolidol has also been reported as one of the volatile components detected in cannabis samples (PMID: 26657499 ). The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520 ). Currently it is also under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs ( Ref:DOI ). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520 ).
Structure
Thumb
Synonyms
ValueSource
(3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olChEBI
(S)-cis-NerolidolChEBI
(+)-cis-NerolidolHMDB
(+)-NerolidolHMDB
(6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
(Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
(Z)-NerolidolHMDB
3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-olHMDB
3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-olHMDB
D-NerolidolHMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
Nerolidol, (Z)-isomerHMDB
Nerolidol, (S-(Z))-isomerHMDB
NerolidolHMDB
Nerolidol, (e)-isomerHMDB
Nerolidol, (S-(e))-isomerHMDB
PeruviolHMDB
[S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olPhytoBank
folic alcoholPhytoBank
cis-(+)-NerolidolPhytoBank
(3S,6Z)-NerolidolPhytoBank
(±)-NerolidolPhytoBank
NerodilolPhytoBank
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
Traditional Name(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
CAS Registry Number142-50-7
SMILES
CC(C)=CCC\C(C)=C/CC[C@](C)(O)C=C
InChI Identifier
InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-/t15-/m1/s1
InChI KeyFQTLCLSUCSAZDY-QKXCFHHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.55ALOGPS
logP4.31ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.01 m³·mol⁻¹ChemAxon
Polarizability27.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(+)-nerolidol, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-45f6e3893a44769001ceSpectrum
GC-MS(+)-nerolidol, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-45f6e3893a44769001ceSpectrum
GC-MS(+)-nerolidol, non-derivatized, GC-MS Spectrumsplash10-00kf-9300000000-5d006438834962306455Spectrum
Predicted GC-MS(+)-nerolidol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4u-9710000000-533a8143456d99d52949Spectrum
Predicted GC-MS(+)-nerolidol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009f-9450000000-0e9301ccd24a06b7cb6bSpectrum
Predicted GC-MS(+)-nerolidol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-nerolidol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0490000000-161e693347ad291e0fbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avr-8930000000-9d44e8ed0962b3b4a6e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9200000000-e773e83c3d163f0457ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ccfe5910ac69a0881b78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0290000000-472fb15ead3e188bca2aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0q29-8920000000-480ab5d82bb26f770cf2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05gi-9730000000-8f73e6a0f1de3af1ba7dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-9300000000-2b7789b2b428dddd2498Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9100000000-2f699f362b83b3293a70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0290000000-9251c836633c797793b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v4i-3930000000-8dc35c7845f0ac5d0fe9Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.293 mg/g dry wt details
9 Lb HammerDetected and Quantified0.381 mg/g dry wt details
97 SageDetected and Quantified0.264 mg/g dry wt details
AdonisDetected and Quantified0.512 mg/g dry wt details
Alien Sour AppleDetected and Quantified0.240 mg/g dry wt details
Alien Sour AppleDetected and Quantified0.24 mg/g dry wt details
Black BossDetected and Quantified0.311 mg/g dry wt details
Blue DreamDetected and Quantified0.800 mg/g dry wt details
Blue DreamDetected and Quantified0.353 mg/g dry wt details
Blue DreamDetected and Quantified0.414 mg/g dry wt details
Blue DreamDetected and Quantified0.794 mg/g dry wt details
Blue DreamDetected and Quantified0.8 mg/g dry wt details
Bob MarleyDetected and Quantified0.264 mg/g dry wt details
ChemdawgDetected and Quantified0.639 mg/g dry wt details
Chemdawg #4Detected and Quantified0.551 mg/g dry wt details
Chemdawg #4Detected and Quantified1.004 mg/g dry wt details
Cookies and CreamDetected and Quantified0.293 mg/g dry wt details
Cosmic LotusDetected and Quantified0.282 mg/g dry wt details
Dairy QueenDetected and Quantified0.134 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.547 mg/g dry wt details
FLODetected and Quantified0.491 mg/g dry wt details
Goji OGDetected and Quantified0.268 mg/g dry wt details
Golden CobraDetected and Quantified0.212 mg/g dry wt details
Golden SageDetected and Quantified0.357 mg/g dry wt details
Gorilla GlueDetected and Quantified0.906 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.693 mg/g dry wt details
Grape StomperDetected and Quantified0.290 mg/g dry wt details
Grape StomperDetected and Quantified0.193 mg/g dry wt details
Grape StomperDetected and Quantified0.29 mg/g dry wt details
Grizzly KushDetected and Quantified0.374 mg/g dry wt details
Hash PlantDetected and Quantified0.570 mg/g dry wt details
Hash PlantDetected and Quantified0.526 mg/g dry wt details
Hash PlantDetected and Quantified0.57 mg/g dry wt details
HemlockDetected and Quantified0.294 mg/g dry wt details
JabberwockyDetected and Quantified0.496 mg/g dry wt details
JabberwockyDetected and Quantified1.266 mg/g dry wt details
Jack HererDetected and Quantified0.529 mg/g dry wt details
Kandy KushDetected and Quantified0.363 mg/g dry wt details
Kush PuppyDetected and Quantified0.519 mg/g dry wt details
La ChocoDetected and Quantified0.486 mg/g dry wt details
Lemon BalmDetected and Quantified0.484 mg/g dry wt details
Lemon GojiDetected and Quantified0.110 mg/g dry wt details
Lemon GojiDetected and Quantified0.11 mg/g dry wt details
Lemon OGDetected and Quantified0.258 mg/g dry wt details
Lemon SherbetDetected and Quantified0.202 mg/g dry wt details
Lemon SkunkDetected and Quantified0.530 mg/g dry wt details
Lemon SkunkDetected and Quantified0.274 mg/g dry wt details
Lemon SkunkDetected and Quantified0.53 mg/g dry wt details
Liberty HazeDetected and Quantified0.116 mg/g dry wt details
LohanDetected and Quantified0.158 mg/g dry wt details
Lucky CharmsDetected and Quantified0.829 mg/g dry wt details
Maui HazeDetected and Quantified0.876 mg/g dry wt details
Moby DickDetected and Quantified0.445 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified0.131 mg/g dry wt details
Nightmare CookieDetected and Quantified0.215 mg/g dry wt details
Orange SkunkDetected and Quantified0.476 mg/g dry wt details
Pineapple SkunkDetected and Quantified0.351 mg/g dry wt details
Pipe DreamDetected and Quantified0.558 mg/g dry wt details
Platinum DelightDetected and Quantified0.354 mg/g dry wt details
Purple EclipseDetected and Quantified0.614 mg/g dry wt details
Rocket FuelDetected and Quantified0.888 mg/g dry wt details
Rollex OGDetected and Quantified0.590 mg/g dry wt details
Rollex OGDetected and Quantified0.59 mg/g dry wt details
Rosetta StoneDetected and Quantified1.068 mg/g dry wt details
SatoriDetected and Quantified0.112 mg/g dry wt details
Skunk HazeDetected and Quantified0.781 mg/g dry wt details
Skywalker OGDetected and Quantified0.629 mg/g dry wt details
SpectrumDetected and Quantified0.243 mg/g dry wt details
Star BudDetected and Quantified0.972 mg/g dry wt details
Star KillerDetected and Quantified0.410 mg/g dry wt details
Star KillerDetected and Quantified0.41 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.341 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.385 mg/g dry wt details
Sunset SherbetDetected and Quantified0.482 mg/g dry wt details
Sunset SherbetDetected and Quantified0.644 mg/g dry wt details
Tangerine DreamDetected and Quantified0.343 mg/g dry wt details
The SauceDetected and Quantified0.798 mg/g dry wt details
Venom OGDetected and Quantified0.491 mg/g dry wt details
White WidowDetected and Quantified0.152 mg/g dry wt details
Wonder WomanDetected and Quantified0.096 mg/g dry wt details
HMDB IDHMDB0035663
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006275
KNApSAcK IDC00034757
Chemspider ID4512192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5356544
PDB IDNot Available
ChEBI ID176337
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  3. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  4. Chan WK, Tan LT, Chan KG, Lee LH, Goh BH: Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Molecules. 2016 Apr 28;21(5). pii: molecules21050529. doi: 10.3390/molecules21050529. [PubMed:27136520 ]
  5. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]