Record Information
Version1.0
Creation date2015-10-09 22:33:29 UTC
Update date2017-01-19 02:36:42 UTC
FoodComEx IDPC000940
FoodDB RecordFDB013792
Chemical Information
NameGeraniol
Descriptionbeta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403)
CAS Number106-24-1
Structure
Thumb
Synonyms
SynonymSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olbiospider
(2E)-3,7-Dimethylocta-2,6-dien-1-olbiospider
(E)-3,7-Dimethyl-2,6-octadien-1-olbiospider
(E)-Geraniolbiospider
(E)-Nerolbiospider
2-trans-3,7-Dimethyl-2,6-octadien-1-olbiospider
2-trans-3,7-dimethyl-2,6-octadiene-1-olbiospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, trans-biospider
2E-Geraniolbiospider
3,7-Dimethyl-(2e)-2,6-octadien-1-olHMDB
3,7-Dimethyl-(e)-2,6-octadien-1-olHMDB
3,7-Dimethyl-2,6-octadien-1-ol, (E)-biospider
3,7-Dimethyl-trans-2,6-octadien-1-olbiospider
b-Geranioldb_source
beta-Geraniolbiospider
FEMA 2507db_source
Geranioldb_source
Geranyl alcoholdb_source
Lemonoldb_source
t-GeraniolChEBI
trans-2,6-Dimethyl-2,6-octadien-8-olbiospider
trans-3,7-Dimethy- octa-2,6-dien-1-olbiospider
trans-3,7-Dimethyl-2,6-octadien-1-olbiospider
trans-Geraniolbiospider
Chemical FormulaC10H18O
IUPAC name(2E)-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-JXMROGBWSA-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 logP3.56GRIFFIN,S ET AL. (1999)
Experimental Water Solubility0.1 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
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, up to 4 g
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
AKSci G461
Toronto Research Chemicals G367000