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Record Information
Version2.0
Creation Date2014-09-11 05:18:39 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4838
Identification
Common Namebeta-Geraniol
ClassSmall Molecule
Descriptionbeta-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.
Compound Type
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(2E)-3,7-Dimethyl-2,6-octadien-1-ol
(2E)-3,7-Dimethylocta-2,6-dien-1-ol
(E)-3,7-Dimethyl-2,6-octadien-1-ol
(E)-Geraniol
(E)-Nerol
2-trans-3,7-Dimethyl-2,6-octadien-1-ol
2-trans-3,7-Dimethyl-2,6-octadiene-1-ol
2E-Geraniol
3,7-Dimethyl-(2E)-2,6-Octadien-1-ol
3,7-Dimethyl-(E)-2,6-Octadien-1-ol
3,7-Dimethyl-trans-2,6-Octadien-1-ol
b-Geraniol
FEMA 2507
Geraniol
Geranyl alcohol
Lemonol
trans-2,6-Dimethyl-2,6-octadien-8-ol
trans-3,7-Dimethy- octa-2,6-dien-1-ol
trans-3,7-Dimethyl-2,6-octadien-1-ol
trans-Geraniol
β-Geraniol
Chemical FormulaC10H18O
Average Molecular Mass154.249 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
SMILES[H]\C(CO)=C(\C)CCC=C(C)C
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 KeyInChIKey=GLZPCOQZEFWAFX-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
LogP3.56
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-002f-9800000000-16b748da465c428492a4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-25934c23f4bc9ba87142JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9000000000-a4d79e7813b94cf0d54bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3a5359aae818f9966cbdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9200000000-4a8a23071f388f446451JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-f24e92e3c3efdc35a606JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-d8e4f64753ef594f6d40JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-2bce8c0905dd12aa5dacJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-9800000000-16b748da465c428492a4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-4900000000-7e43c8601ed65028cae5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-1900000000-710389d2548f45d60502JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-001r-9500000000-d864036a8f8b4cdb20aeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-001r-9400000000-e3661fd0b608943d6b6cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-001i-9200000000-d748b4cd92b7c69ffee3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-001i-9100000000-b6abc8d3af3aa99879b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-9000000000-710e0ba546f9b86b8e40JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-001i-9000000000-4cc179896d0516270659JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-001i-9000000000-7f3a48636d9da2cda821JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-001i-9000000000-4b196d3d8e84ecd0e9f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-003r-9000000000-718f1d4e975f4b2446d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-003u-9000000000-2e43acc8a377504a4329JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-005c-9000000000-fe7ffaf2c7e121c33b7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-005c-9000000000-467c307d1f0822b86ea0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-005c-9000000000-5939202301ea6107df2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-002f-9000000000-0e13687577d30f6265ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f96-9000000000-e478c8b2587c1134117dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-5f3fc91bdf843e40a266JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-ab16b7d86a06d659d4f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-3900000000-4dd10bbea41237cba535JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1900000000-3d437630e5bec67a7e07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-0e505c85cec6344cab5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-c7400df359a9559bd594JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-113756054eed13d33ee4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-dea43b41c5b791cef9d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800000000-c028a2bd655026094251JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-f59382e51acd0b540204JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB35155
PubChem Compound ID637566
ChEMBL IDCHEMBL25719
ChemSpider ID13849989
KEGG IDC01500
UniProt IDNot Available
OMIM ID
ChEBI ID17447
BioCyc IDNot Available
CTD IDC007836
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkGeraniol
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically binds 9-cis retinoic acid (9C-RA).
Gene Name:
RXRB
Uniprot ID:
P28702
Molecular Weight:
56921.38 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC508.06 uMATG_RXRb_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Transmembrane signaling receptor activity
Specific Function:
Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. Involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL. Can be activated by endogenous compounds, including 12-hydroperoxytetraenoic acid and bradykinin. Acts as ionotropic endocannabinoid receptor with central neuromodulatory effects. Triggers a form of long-term depression (TRPV1-LTD) mediated by the endocannabinoid anandamine in the hippocampus and nucleus accumbens by affecting AMPA receptors endocytosis (By similarity). Activation by vanilloids, like capsaicin, and temperatures higher than 42 degrees Celsius, exhibits a time- and Ca(2+)-dependent outward rectification, followed by a long-lasting refractory state. Mild extracellular acidic pH (6.5) potentiates channel activation by noxious heat and vanilloids, whereas acidic conditions (pH <6) directly activate the channel.
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular Weight:
94955.33 Da
References
  1. Ohkawara S, Tanaka-Kagawa T, Furukawa Y, Nishimura T, Jinno H: Activation of the human transient receptor potential vanilloid subtype 1 by essential oils. Biol Pharm Bull. 2010;33(8):1434-7. [20686244 ]