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Showing Compound Nerolidiol (FDB006275)

Record Information
Version1.0
Creation date2010-04-08 22:07:04 UTC
Update date2020-09-17 15:33:54 UTC
Primary IDFDB006275
Secondary Accession Numbers
  • FDB014379
Chemical Information
FooDB NameNerolidiol
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. 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 (https://doi.org/10.1016/S0939-6411(01)00166-7). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520).
CAS Number142-50-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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
Chemical FormulaC15H26O
IUPAC name(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
InChI IdentifierInChI=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
Isomeric SMILESC=C[C@@](C)(O)CC\C=C(\C)CCC=C(C)C
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
Classification
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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNerolidiol, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-45f6e3893a44769001ceSpectrum
GC-MSNerolidiol, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-45f6e3893a44769001ceSpectrum
GC-MSNerolidiol, non-derivatized, GC-MS Spectrumsplash10-00kf-9300000000-5d006438834962306455Spectrum
Predicted GC-MSNerolidiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4u-9710000000-533a8143456d99d52949Spectrum
Predicted GC-MSNerolidiol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009f-9450000000-0e9301ccd24a06b7cb6bSpectrum
Predicted GC-MSNerolidiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNerolidiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0490000000-161e693347ad291e0fbd2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avr-8930000000-9d44e8ed0962b3b4a6e52016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9200000000-e773e83c3d163f0457dd2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ccfe5910ac69a0881b782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0290000000-472fb15ead3e188bca2a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0q29-8920000000-480ab5d82bb26f770cf22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05gi-9730000000-8f73e6a0f1de3af1ba7d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-9300000000-2b7789b2b428dddd24982021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9100000000-2f699f362b83b3293a702021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0290000000-9251c836633c797793b32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v4i-3930000000-8dc35c7845f0ac5d0fe92021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNEROLIDIOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).