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+
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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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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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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Phythochemical screening and anticonvulsant activity of Cymbopogon winterianus Jowitt (Poaceae) leaf essential oil in rodents. | 2008 Aug |
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Activation of the human transient receptor potential vanilloid subtype 1 by essential oils. | 2010 |
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Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes. | 2010 Nov 10 |
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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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Preclinical renal cancer chemopreventive efficacy of geraniol by modulation of multiple molecular pathways. | 2011 Nov 28 |
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Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. | 2013 Dec |
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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.
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Classification Tree | Code System | Code | ||
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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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Code System | Code | Type | Description | ||
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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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ACTIVE MOIETY
METABOLITE (PARENT)