beta-Geraniol (CHEM003794)

Record Information
Version1.0
Creation Date2014-09-11 05:18:39 UTC
Update Date2026-05-14 19:41:51 UTC
Accession NumberCHEM003794
Identification
Common Namebeta-Geraniol
ClassSmall Molecule
Description
beta-Geraniol is found in almond. beta-Geraniol is found in free state and as esters in many essential oils including geranium oil. Most prolific natural source is palmarosa oil. beta-Geraniol is a flavouring agent. Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type). It also occurs in small quantities in geranium, lemon, and many other essential oils. It has a rose-like odor and is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. It is the isomer of nerol. (Wikipedia) beta-Geraniol belongs to the family of Monoterpenes. These are compounds contaning a chain of two isoprene units.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(2E)-GeraniolChEBI
(e)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(e)-GeraniolChEBI
(e)-NerolChEBI
2-trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
3,7-Dimethyl-trans-2,6-octadien-1-olChEBI
Geranyl alcoholChEBI
LemonolChEBI
t-GeraniolChEBI
trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
trans-GeraniolChEBI
b-GeraniolGenerator
Β-geraniolGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-(e)-2,6-octadien-1-olHMDB
FEMA 2507HMDB
GeraniolHMDB
trans-2,6-Dimethyl-2,6-octadien-8-olHMDB
trans-3,7-Dimethy- octa-2,6-dien-1-olHMDB
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
NerolMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
Geraniol, (e)-isomerMeSH
(E)-3,7-Dimethyl-2,6-octadienolPhytoBank
trans-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-GeraniolPhytoBank
Chemical FormulaC10H18O
Average Molecular Mass154.253 g/mol
Monoisotopic Mass154.136 g/mol
CAS Registry Number106-24-1
IUPAC Name(2E)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namegeraniol
SMILESCC(C)=CCC\C(C)=C\CO
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
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< -15 °C
Boiling PointNot Available
Solubility0.1 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0035155
FooDB IDFDB013792
Phenol Explorer IDNot Available
KNApSAcK IDC00000845
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGeraniol
Chemspider ID13849989
ChEBI ID17447
PubChem Compound ID637566
Kegg Compound IDC01500
YMDB IDYMDB01700
ECMDB IDM2MDB005582
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18824010
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20573166
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23102596
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23108028
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23168261
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23200656
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23399806
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23415329
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23499697
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23510343
11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
12. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
13. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
14. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
15. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
16. The lipid handbook with CD-ROM