U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 NEROL

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-

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
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
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004 Feb
Geraniol, a component of plant essential oils, modulates DNA synthesis and potentiates 5-fluorouracil efficacy on human colon tumor xenografts.
2004 Nov 8
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.
2005 Jul
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.
2007 Oct
Activation of the human transient receptor potential vanilloid subtype 1 by essential oils.
2010
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
Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species.
2012 Sep 3
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 19:08:53 UTC 2023
Edited
by admin
on Fri Dec 15 19:08:53 UTC 2023
Record UNII
38G5P53250
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEROL
FCC   FHFI   MI  
Systematic Name English
(Z)-GERANIOL
Systematic Name English
CIS-3,7-DIMETHYL-2,6-OCTADIEN-1-OL
Common Name English
NERYL ALCOHOL
Systematic Name English
NEROL 900
Common Name English
.BETA.-NEROL
Common Name English
FEMA NO. 2770
Code English
NSC-46105
Code English
(2Z)-3,7-DIMETHYLOCTA-2,6-DIEN-1-OL
Systematic Name English
NEROL [MI]
Common Name English
NEROL [FCC]
Common Name English
NEROL [FHFI]
Common Name English
(Z)-NEROL
Systematic Name English
2-CIS-3,7-DIMETHYL-2,6-OCTADIEN-1-OL
Systematic Name English
2,6-OCTADIEN-1-OL, 3,7-DIMETHYL-, (2Z)-
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION NEROL
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
Code System Code Type Description
RXCUI
2274605
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
HSDB
8262
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
NSC
46105
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
WIKIPEDIA
NEROL
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
MESH
C007836
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
DAILYMED
38G5P53250
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
CHEBI
29452
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
JECFA MONOGRAPH
1233
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-378-7
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
FDA UNII
38G5P53250
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
MERCK INDEX
m7830
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3026728
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
SMS_ID
100000138757
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
CAS
106-25-2
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
EVMPD
SUB78702
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY
PUBCHEM
643820
Created by admin on Fri Dec 15 19:08:53 UTC 2023 , Edited by admin on Fri Dec 15 19:08:53 UTC 2023
PRIMARY