35995
Eugenol
PESTANAL®, analytical standard
Synonym(s):
2-Methoxy-4-(2-propenyl)phenol, 4-Allyl-2-methoxyphenol, 4-Allylguaiacol
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About This Item
Linear Formula:
4-(H2C=CHCH2)C6H3-2-(OCH3)OH
CAS Number:
Molecular Weight:
164.20
Beilstein:
1366759
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
grade
analytical standard
Quality Level
product line
PESTANAL®
Assay
99.6% (GC)
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
refractive index
n20/D 1.541 (lit.)
bp
254 °C (lit.)
mp
−12-−10 °C (lit.)
density
1.067 g/mL at 25 °C (lit.)
application(s)
agriculture
cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care
format
neat
SMILES string
COc1cc(CC=C)ccc1O
InChI
1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChI key
RRAFCDWBNXTKKO-UHFFFAOYSA-N
Gene Information
human ... UGT1A4(54657)
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General description
Eugenol is a naturally occurring flavor extract isolated from the plants, including kernels of Myristica fragrans Houtt, bark of the genus Cinnamonum, roots of Valeriana officinalis, etc. It finds applications as a substrate for vanillin production via enzymatic transformation. Eugenol is released from clove-bud-containing cigarettes, and reportedly exhibits analgesic property, which helps to reduce the pain in the lungs and throat by freezing the pain receptors in the mouth and throat.
Eugenol is a phenolic compound and a major constituent of clove oil, which can find applications as an anti H. pylori agents and anti-bacterial agents. It can also act like a fungicidal agent, which can completely inhibit the growth of Saccharomyces cerevisiae, a species of yeast.
Application
Eugenol may be used as an analytical reference standard for the quantification of the analyte in the following:
- Bioconversion broth using reversed-phase high-performance liquid chromatography with UV detection (RP-HPLC-UV).
- Mainstream cigarette smoke using gas chromatography/mass spectrometry (GC/MS).
- Plant extracts using high-performance thin-layer chromatography (HPTLC) and gas chromatography coupled to mass spectrometry (GC-MS).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Other Notes
This compound is commonly found in plants of the genus: angelica cinnamomum
Recommended products
Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
Legal Information
PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Sens. 1
WGK
WGK 1
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Surface alteration of Saccharomyces cerevisiae induced by thymol and eugenol
Bennis.S, et al.
Letters in Applied Microbiology, 38, 454-458 (2004)
Antimicrobial activities of Eugenol and Cinnamaldehyde against the human gastric pathogen Helicobacter pylori
Ali MS, et al.
Annals of Clinical Microbiology and Antimicrobials, 4, 20-20 (2005)
Determination of vanillin, eugenol and isoeugenol by RP-HPLC.
Li-H-Y, et al.
Chromatographia, 60(11-12), 709-713 (2004)
I U Fischer et al.
Journal of chromatography, 525(2), 369-377 (1990-02-23)
The high-performance liquid chromatographic assay described permitted a simple, rapid, sensitive, selective and precise quantitative determination of eugenol in body fluids (serum, urine and bile) without derivatization. Amounts in the range 0.02-100 micrograms of eugenol per millilitre of body fluid
Hyang Nam et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 55, 106-112 (2013-01-15)
The oxidative damage of lipid, protein and DNA is known to be involved in chronic inflammation as well as metastasis. It has been highlighted for searching natural compounds without toxicity to prevent development of these diseases. Thus, it was investigated
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