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Supelco

Eugenol

PESTANAL®, analytical standard

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Synonym(s):
2-Methoxy-4-(2-propenyl)phenol, 4-Allyl-2-methoxyphenol, 4-Allylguaiacol
Linear Formula:
4-(H2C=CHCH2)C6H3-2-(OCH3)OH
CAS Number:
97-53-0
Molecular Weight:
164.20
Beilstein:
1366759
EC Number:
202-589-1
MDL number:
MFCD00008654
PubChem Substance ID:
329755246
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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.

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Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317 - H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

255.2 °F - closed cup

Flash Point(C)

124 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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25G
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705578-5MG-PW

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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)
HPTLC and GC-MS for separation and identification of eugenol in plants
Rusu LM, et al.
J. Planar Chromatogr., 20(2), 139-140 (2007)
Determination of eugenol, anethole, and coumarin in the mainstream cigarette smoke of Indonesian clove cigarettes
Polzin MG, et al.
Food And Chemical Toxicology, 45(10), 1948-1953 (2007)
Determination of vanillin, eugenol and isoeugenol by RP-HPLC.
Li-H-Y, et al.
Chromatographia, 60(11-12), 709-713 (2004)
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