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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
Structure of GERANIOL

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+

HIDE SMILES / InChI

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

PubMed

PubMed

TitleDatePubMed
Antifungal properties of essential oils and their main components upon Cryptococcus neoformans.
1994 Dec
Expression and characterization of a lepidopteran general odorant binding protein.
1997 May
Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.
1998 Feb
Antimycobacterial plant terpenoids.
2001 Nov
Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors.
2004 Dec
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004 Feb
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.
2005 Jul
Effects of beer and hop on ionotropic gamma-aminobutyric acid receptors.
2006 Apr 5
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.
2007 Oct
Phythochemical screening and anticonvulsant activity of Cymbopogon winterianus Jowitt (Poaceae) leaf essential oil in rodents.
2008 Aug
The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity.
2008 Aug 11
Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes.
2010 Nov 10
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011 Dec
Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum.
2011 May
Preclinical renal cancer chemopreventive efficacy of geraniol by modulation of multiple molecular pathways.
2011 Nov 28
Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species.
2012 Sep 3
Finding the optimal patch test material and test concentration to detect contact allergy to geraniol.
2013 Apr
Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans.
2013 Dec
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
Mitigation of acrylamide-induced behavioral deficits, oxidative impairments and neurotoxicity by oral supplements of geraniol (a monoterpene) in a rat model.
2014 Nov 5
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

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 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 Fri Dec 15 15:07:04 UTC 2023
Edited
by admin
on Fri Dec 15 15:07:04 UTC 2023
Record UNII
L837108USY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GERANIOL
FCC   FHFI   HSDB   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
LEMONOL
Common Name English
Geraniol [WHO-DD]
Common Name English
GERANIOL [MI]
Common Name English
GERANIOL [MART.]
Common Name English
GERANIOL [HSDB]
Common Name English
TRANS-3,7-DIMETHYL-2,6-OCTADIEN-8-OL
Common Name English
GERANIOL [FCC]
Common Name English
GERANIOL [FHFI]
Common Name English
NSC-9279
Code English
FEMA NO. 2507
Code English
GERANIOL [INCI]
Common Name English
(E)-3,7-DIMETHYL-2,6-OCTADIEN-1-OL
Systematic Name English
Classification Tree Code System Code
DSLD 4133 (Number of products:3)
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
EPA PESTICIDE CODE 597501
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
NCI_THESAURUS C68542
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
JECFA EVALUATION GERANIOL
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
Code System Code Type Description
JECFA MONOGRAPH
1232
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
FDA UNII
L837108USY
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
MERCK INDEX
m5707
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
GERANIOL
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
NCI_THESAURUS
C63668
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
DRUG BANK
DB14183
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
EVMPD
SUB50997
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
SMS_ID
100000133470
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
RXCUI
1368875
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY Increased Histamine Release [PE]
PUBCHEM
637566
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
HSDB
484
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
MESH
C007836
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-377-1
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
NSC
9279
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
CAS
106-24-1
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID8026727
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
CHEBI
17447
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
DAILYMED
L837108USY
Created by admin on Fri Dec 15 15:07:04 UTC 2023 , Edited by admin on Fri Dec 15 15:07:04 UTC 2023
PRIMARY
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