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Nerol (PC000941)

Record Information
Version1.0
Creation date2015-10-09 22:33:30 UTC
Update date2017-01-19 02:36:42 UTC
FoodComEx IDPC000941
FoodDB RecordFDB014945
Chemical Information
NameNerol
DescriptionNerol or (Z)-3,7-dimethyl-2,6-octadien-1-ol or cis-Geranial is formally classified as an alkylalcohol although it is biochemically a monoterpenoid synthesized from isoprene units. It is soluble in water and very soluble in alcohol. Nerol is a naturally occurring organic compound found in the essential oils of many plants and was originally found in neroli oil, from which its name was derived. The largest natural source is palmarosa oil and it is the primary constituent of rose oil, palmarosa oil, and citronella oil (Java type) with in small quantities found in geranium, lemon, and many other essential oils. Different foods contain nerol with the highest concentration found in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. Nerol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. Nerol has a sweet, citrus and floral flavor with a sweet rose-like odor. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. This alcohol is widely and frequently used in perfumery as it has a freshness to a rose base (PMID: 18640199). It is detected in small quantities in orange peel and together with other oils, was found to have antimicrobial properties (PMID: 27535797).
CAS Number106-25-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(2e)3,7-Dimethyl-2,6-octadien-1-olHMDB
(2Z)-3,7-Dimethyl-2,6-octadien-1-olbiospider
(2Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
(cis)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-octadien-1-olHMDB
(Z)-3,7-dimethyl-2,6-Octadien-1-olbiospider
(Z)-3,7-Dimethylocta-2,6-dien-1-olChEBI
(Z)-Geraniolbiospider
(Z)-Nerolmanual
(Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
2-cis-3,7-Dimethyl-2,6-octadien-1-olbiospider
2,6-Dimethyl-trans-2,6-octadien-8-olHMDB
2,6-Octadien-1-ol, 3,7-dimethyl-, (2Z)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-biospider
3,7-Dimethyl-2,6-octadien-1-olHMDB
3,7-Dimethyl-octane-1-ol tetrahydro derivativeHMDB
3,7-Dimethyl-trans-2, 6-octadien-1-olHMDB
3,7-Dimethylocta-2,6-dien-1-olHMDB
beta-Neroldb_source
cis-3,7-Dimethyl-2,6-octadien-1-olbiospider
cis-Geraniolbiospider
FEMA 2770db_source
Geraniol (natural)HMDB
Geraniol alcoholHMDB
GuaniolHMDB
Neroldb_source
Nerol (natural)HMDB
Nerolidyl diateHMDB
Neryl alcoholdb_source
VernolHMDB
Chemical FormulaC10H18O
IUPAC name(2Z)-3,7-dimethylocta-2,6-dien-1-ol
InChI IdentifierInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
InChI KeyGLZPCOQZEFWAFX-YFHOEESVSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C/CO
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP3.47GRIFFIN,S ET AL. (1999)
Experimental Water Solubility0.531 mg/mL at 25 oCMILLER,DJ & HAWTHORNE,SB (2000A)
Melting Point<-15 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request
Delivery TimeNot Available
Storage Formliquid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Acros Organics HMDB0005812
AKSci M755
MetaSci HMDB0005812
Toronto Research Chemicals N390095