T3DB: beta-Geraniol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (4)XML

Targets (4)

Record Information

Version

2.0

Creation Date

2014-09-11 05:18:39 UTC

Update Date

2014-12-24 20:26:58 UTC

Accession Number

T3D4838

Identification

Common Name

beta-Geraniol

Class

Small 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.

Compound Type

Flavouring Agent
Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

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 Formula

C₁₀H₁₈O

Average Molecular Mass

154.249 g/mol

Monoisotopic Mass

154.136 g/mol

CAS Registry Number

106-24-1

IUPAC Name

(2E)-3,7-dimethylocta-2,6-dien-1-ol

Traditional Name

geraniol

SMILES

[H]\C(CO)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+

InChI Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17447 )
monoterpenoid (CHEBI:17447 )
3,7-dimethylocta-2,6-dien-1-ol (CHEBI:17447 )
Acyclic monoterpenoids (C01500 )
Linear monoterpenes (C01500 )
Acyclic monoterpenoids (LMPR0102010016 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< -15 °C
Boiling Point	Not Available
Solubility	0.1 mg/mL at 25 °C
LogP	3.56

Predicted Properties

Property	Value	Source
Water Solubility	1.37 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.18 m³·mol⁻¹	ChemAxon
Polarizability	19.67 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-002f-9800000000-16b748da465c428492a4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-25934c23f4bc9ba87142	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9000000000-a4d79e7813b94cf0d54b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3a5359aae818f9966cbd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9200000000-4a8a23071f388f446451	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-f24e92e3c3efdc35a606	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-d8e4f64753ef594f6d40	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-2bce8c0905dd12aa5dac	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-9800000000-16b748da465c428492a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-4900000000-7e43c8601ed65028cae5	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014u-9300000000-c85bc4c928fbf7d824e8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-030c-9520000000-69b7fbbb25764f7b612e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-1900000000-710389d2548f45d60502	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-001r-9500000000-d864036a8f8b4cdb20ae	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-001r-9400000000-e3661fd0b608943d6b6c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-001i-9200000000-d748b4cd92b7c69ffee3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-001i-9100000000-b6abc8d3af3aa99879b4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-001i-9000000000-710e0ba546f9b86b8e40	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-001i-9000000000-4cc179896d0516270659	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-001i-9000000000-7f3a48636d9da2cda821	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-001i-9000000000-4b196d3d8e84ecd0e9f3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-003r-9000000000-718f1d4e975f4b2446d1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-003u-9000000000-2e43acc8a377504a4329	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-005c-9000000000-fe7ffaf2c7e121c33b7c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-005c-9000000000-467c307d1f0822b86ea0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-005c-9000000000-5939202301ea6107df2c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-002f-9000000000-0e13687577d30f6265cc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0f96-9000000000-e478c8b2587c1134117d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-5f3fc91bdf843e40a266	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-ab16b7d86a06d659d4f3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-3900000000-4dd10bbea41237cba535	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-3d437630e5bec67a7e07	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-8900000000-0e505c85cec6344cab5c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-c7400df359a9559bd594	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-113756054eed13d33ee4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0900000000-dea43b41c5b791cef9d2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9800000000-c028a2bd655026094251	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-f59382e51acd0b540204	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

17447

BioCyc ID

Not Available

CTD ID

C007836

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Geraniol

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Estrogen receptor

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

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 ]

Target Details

2. Estrogen receptor beta

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

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 ]

Target Details

3. Retinoic acid receptor RXR-beta

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

Type	Value	Assay Type	Assay Source
AC50	8.06 uM	ATG_RXRb_TRANS	Attagene

References

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 ]

Target Details

4. Transient receptor potential cation channel subfamily V member 1

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

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 ]

beta-Geraniol (T3D4838)

Structure for T3D4838: beta-Geraniol

Targets

References

References

Binding/Activity Constants

References

References