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Merck

35995

Eugenol

PESTANAL®, analytical standard

Sinónimos:

2-Methoxy-4-(2-propenyl)phenol, 4-Allyl-2-methoxyphenol, 4-Allylguaiacol

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Fórmula lineal:
4-(H2C=CHCH2)C6H3-2-(OCH3)OH
Número CAS:
97-53-0
Peso molecular:
164.20
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329755246
EC Number:
202-589-1
Beilstein/REAXYS Number:
1366759
MDL number:
MFCD00008654

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Nombre del producto

Eugenol, PESTANAL®, analytical standard

InChI key

RRAFCDWBNXTKKO-UHFFFAOYSA-N

InChI

1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

SMILES string

COc1cc(CC=C)ccc1O

grade

analytical standard

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

Quality Level

100

Gene Information

human ... UGT1A4(54657)

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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.

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.

Other Notes

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.
This compound is commonly found in plants of the genus: angelica cinnamomum

Legal Information

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Clase de almacenamiento

10 - Combustible liquids

wgk

WGK 1

flash_point_f

255.2 °F - closed cup

flash_point_c

124 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
BCCL5331
BCCH3111
BCCC7425
BCBV3232
BCBT4549

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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)
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 vanillin, eugenol and isoeugenol by RP-HPLC.
Li-H-Y, et al.
Chromatographia, 60(11-12), 709-713 (2004)
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