Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C/CO
InChI
InChIKey=GLZPCOQZEFWAFX-YFHOEESVSA-N
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Geraniol is a dietary monoterpene alcohol that
is found in the essential oils of aromatic plants. To date,
experimental evidence supports the therapeutic or preventive
effects of geraniol on different types of cancer, such as breast,
lung, colon, prostate, pancreatic, and hepatic cancer, and has
revealed the mechanistic basis for its pharmacological actions.
In addition, geraniol sensitizes tumor cells to commonly used
chemotherapy agents. Geraniol controls a variety of signaling
molecules and pathways that represent tumor hallmarks;
these actions of geraniol constrain the ability of tumor cells
to acquire adaptive resistance against anticancer drugs. It has been shown that geraniol inhibits
HMG-CoA reductase in most types of tumor cells, which
raises the possibility that the reduced prenylation of small
G-proteins, such as Ras or RhoA, accounts for the antitumor
effects of geraniol. In addition to its use in various commercial
products, including cosmetics and fine fragrances, geraniol
exerts a broad spectrum of pharmacological activities, such
as anti-microbial, anti-inflammatory, anti-oxidant, anti-ulcer
and neuroprotective activities. Geraniol is classified into the generally recognized-as-safe
(GRAS) category by the Flavor and
Extract Manufacturers Association (FEMA) and the Food
and Drug Administration (FDA) of the United States.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25963227 |
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Target ID: CHEMBL612867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20337938 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study. | 1998 Feb |
|
Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors. | 2004 Dec |
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Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. | 2004 Feb |
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Geraniol, a component of plant essential oils, modulates DNA synthesis and potentiates 5-fluorouracil efficacy on human colon tumor xenografts. | 2004 Nov 8 |
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Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol. | 2005 Jul |
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Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. | 2007 Oct |
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Activation of the human transient receptor potential vanilloid subtype 1 by essential oils. | 2010 |
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An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8. | 2011 Dec |
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Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum. | 2011 May |
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Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species. | 2012 Sep 3 |
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Mitigation of acrylamide-induced behavioral deficits, oxidative impairments and neurotoxicity by oral supplements of geraniol (a monoterpene) in a rat model. | 2014 Nov 5 |
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Acetylcholinesterase activity of electric eel is increased or decreased by selected monoterpenoids and phenylpropanoids in a concentration-dependent manner. | 2015 Mar 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7472655
Rats: In the first study, geraniol (23 mmol/kg diet, 350 umol/d) was fed to male buffalo rats for 14 d before and for 42 d after the transplant of Morris 7777 hepatomas. Tumor growth was suppressed.
Mice: In the second study, the dose-dependent impact of geraniol on the growth of B16 melanomas was assessed. Dietary geraniol (0.65, 6.5 and 65 mmol/kg diet) was fed to female C57BL mice for 14 d before and for 21 d after tumor transplant. Tumor growth was suppressed by 6.5 and 65 mmol geraniol/kg diet.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11961066
In Caco-2 cells at confluency, geraniol (400 uM) prevented the formation of brush-border membranes and inhibited the expression of intestinal hydrolases (sucrase, lactase, alkaline phosphatase). The antiproliferative effect of geraniol (400 uM) together with 5-FU (5 uM) was twice that of 5-FU alone.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:08:53 UTC 2023
by
admin
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Fri Dec 15 19:08:53 UTC 2023
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Record UNII |
38G5P53250
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Record Status |
Validated (UNII)
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JECFA EVALUATION |
NEROL
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CFR |
21 CFR 172.515
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