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-JXMROGBWSA-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 |
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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 |
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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 |
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Antifungal properties of essential oils and their main components upon Cryptococcus neoformans. | 1994 Dec |
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Expression and characterization of a lepidopteran general odorant binding protein. | 1997 May |
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Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study. | 1998 Feb |
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Antimycobacterial plant terpenoids. | 2001 Nov |
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Assessment of estrogenic activity in some common essential oil constituents. | 2002 Nov |
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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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Effects of beer and hop on ionotropic gamma-aminobutyric acid receptors. | 2006 Apr 5 |
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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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Preclinical renal cancer chemopreventive efficacy of geraniol by modulation of multiple molecular pathways. | 2011 Nov 28 |
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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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Finding the optimal patch test material and test concentration to detect contact allergy to geraniol. | 2013 Apr |
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Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. | 2013 Dec |
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Gene expression regulation of Bcl2, Bax and cytochrome-C by geraniol on chronic MPTP/probenecid induced C57BL/6 mice model of Parkinson's disease. | 2014 Jun 25 |
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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
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admin
on
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Record UNII |
L837108USY
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
4133 (Number of products:3)
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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NCI_THESAURUS |
C275
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EPA PESTICIDE CODE |
597501
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NCI_THESAURUS |
C68542
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NDF-RT |
N0000185508
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JECFA EVALUATION |
GERANIOL
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1232
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L837108USY
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m5707
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PRIMARY | Merck Index | ||
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GERANIOL
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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C63668
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DB14183
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SUB50997
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100000133470
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1368875
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PRIMARY | RxNorm | ||
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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637566
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484
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C007836
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203-377-1
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9279
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106-24-1
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DTXSID8026727
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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17447
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L837108USY
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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METABOLITE -> PARENT |
Rat urine
IN-VIVO
URINE
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ACTIVE MOIETY |