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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 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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Curative
Unknown
Curative
Unknown
Primary
Unknown
Primary
Unknown

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
38G5P53250
Record Status Validated (UNII)
Record Version