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Merck

04607

Methyl eugenol

analytical standard

Synonym(s):

Eugenol methyl ether, 4-Allyl-1,2-dimethoxybenzene, Eugenyl methyl ether

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About This Item

Linear Formula:
H2C=CHCH2C6H3(OCH3)2
CAS Number:
93-15-2
Molecular Weight:
178.23
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329747954
EC Number:
202-223-0
Beilstein/REAXYS Number:
1910871
MDL number:
MFCD00008652

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InChI

1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3

SMILES string

COc1ccc(CC=C)cc1OC

InChI key

ZYEMGPIYFIJGTP-UHFFFAOYSA-N

grade

analytical standard

assay

>98% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

Quality Level

100

refractive index

n20/D 1.534 (lit.)

bp

254-255 °C (lit.)

mp

−4 °C (lit.)

density

1.036 g/mL at 25 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

storage temp.

2-8°C

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General description

Methyl eugenol is a phenyl methyl ether belonging to the class of alkylbenzenes. It is derived from eugenol and commonly identified as one of the important components of basil essential oil. It is widely used as an active pesticide ingredient and also employed as an insect parapheromone in insect traps, to attract certain species such as oriental fruit flies.

Application

Methyl eugenol may be used as an analytical reference standard for the quantification of the analyte in the following:        
  • Essential oil of Pimenta pseudocaryophyllus using high-performance liquid chromatography (HPLC). The purity of the extracted compound is then determined by gas chromatography coupled to flame ionization detector (GC/FID).       
  • Stem bark of Cinnamomum zeylanicum Blume using reversed-phase high-performance liquid chromatography (RP-HPLC) with UV-visible detection.       
  • Rosa hybrida using gas-chromatography coupled to mass spectrometry (GC-MS) technique.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Muta. 2

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 3 petroleums + Hazardous rank III + Water insoluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

04607-BULK: + 04607-VAR: + 04607-50MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC0277
BCBV6695

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Benefits of the Mediterranean Diet in the Elderly Patient (2018)
Weiwei Zheng et al.
Journal of insect physiology, 58(8), 1122-1127 (2012-05-29)
Bactrocera dorsalis is a destructive fruit-eating pest that causes severe economic damage to the fruit and vegetable industry. Methyl eugenol (ME) has been widely used as an effective sexual attractant for male fruit flies through olfactory perception. However, the molecular
Wei Ding et al.
Toxicological sciences : an official journal of the Society of Toxicology, 123(1), 103-112 (2011-06-11)
Methyleugenol (MEG), a constituent of human food, induces malignant tumors in multiple tissues of rats and mice. Although MEG forms DNA adducts and induces unscheduled DNA synthesis in rat liver, it is negative in many in vitro genetic toxicity assays.
D McInnis et al.
Journal of economic entomology, 104(6), 1969-1978 (2012-02-04)
Males of the oriental fruit fly, Bactrocera dorsalis (Hendel), are strongly attracted to methyl eugenol (ME), and recent work demonstrated that ingestion of this chemical enhances male mating success, apparently owing its role as a precursor in the synthesis of
Alexander T Cartus et al.
Toxicological sciences : an official journal of the Society of Toxicology, 129(1), 21-34 (2012-05-23)
Methyleugenol (1) is a constituent of many foods, in particular of herbal spices, and is used as flavoring agent in foodstuffs and as fragrance in cosmetics. 1 has been found to be carcinogenic in rodents, its metabolite, 1-hydroxymethyleugenol (2) acting
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