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Isoeugenol

analytical standard

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Synonym(s):
2-Methoxy-4-propenylphenol
Linear Formula:
CH3OC6H3(CH=CHCH3)OH
CAS Number:
97-54-1
Molecular Weight:
164.20
Beilstein:
1909602
EC Number:
202-590-7
MDL number:
MFCD00009285
UNSPSC Code:
85151701
PubChem Substance ID:
329754773
NACRES:
NA.24

grade

analytical standard

Quality Level

100

vapor density

>1 (vs air)

vapor pressure

<0.01 mmHg ( 20 °C)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.575 (lit.)

bp

132 °C/10 mmHg (lit.)

density

1.084 g/cm3

application(s)

cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care

format

neat

SMILES string

OC1=CC=C(/C=C/C)C=C1OC

InChI

1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+

InChI key

BJIOGJUNALELMI-ONEGZZNKSA-N

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General description

Isoeugenol belongs to the class of phenylpropenes, naturally occurring in the essential oils of plants. It can also be obtained from eugenol by isomerization. It has been used as a substrate in the preparation of vanillin via enzymatic transformation by lipoxygenase enzyme.

Application

Isoeugenol may be used as an analytical reference standard for the determination of the analyte in bioconversion broth using reversed-phase high-performance liquid chromatography with ultraviolet detection (RP-HPLC-UV).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1A - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

233.6 °F

Flash Point(C)

112 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The monolignol pathway contributes to the biosynthesis of volatile phenylpropenes in flowers.
Muhlemann KJ, et al.
The New phytologist, 204(3), 661-670 (2014)
Determination of vanillin, eugenol and isoeugenol by RP-HPLC.
Li-H-Y, et al.
Chromatographia, 60(11-12), 709-713 (2004)
Michaela Kalmes et al.
Journal of toxicology and environmental health. Part A, 75(8-10), 478-491 (2012-06-13)
The phenolic derivatives eugenol and isoeugenol, which are naturally found in essential oils of different spices, are commonly used as fragrances. Recently data demonstrated that growth suppression produced by these substances occurs in keratinocytes and that the effects may be
J Krupa et al.
The journal of physical chemistry. B, 116(36), 11148-11158 (2012-07-26)
In situ photochemical transformations of monomers of 2-methoxy-4-(prop-1-enyl)phenol (isoeugenol) and 2-methoxy-4-(prop-2-enyl)phenol (eugenol) isolated in low temperature matrices were induced by tunable UV laser light, and the progress of the reactions was followed by FTIR spectroscopy. Conformer-selective E ↔ Z geometrical
Aurélie Frankart et al.
Archives of dermatological research, 304(4), 289-303 (2012-01-25)
Models of reconstructed human epidermis (RHE) holding proliferating and fully differentiated cultured keratinocytes allow in vitro investigation of early molecular and cellular epidermal events during the complex response of keratinocytes at the onset of allergic contact dermatitis (ACD) or sensitization.
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