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ISOEUGENOL

Basic information Description References Safety Related Supplier

ISOEUGENOL Basic information

Product Name:
ISOEUGENOL
CAS:
97-54-1
MF:
C10H12O2
MW:
164.2
EINECS:
202-590-7
Mol File:
97-54-1.mol
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ISOEUGENOL Chemical Properties

Melting point:
-10 °C
Boiling point:
266 °C
Density 
1.082 g/mL at 25 °C
vapor density 
>1 (vs air)
vapor pressure 
<0.01 mm Hg ( 20 °C)
refractive index 
n20/D 1.575(lit.)
FEMA 
2468 | ISOEUGENOL
Flash point:
>230 °F
storage temp. 
0-6°C
form 
Viscous Liquid
pka
10.10±0.31(Predicted)
color 
Clear yellow
Merck 
14,5171
JECFA Number
1260
BRN 
1909602
Stability:
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
97-54-1(CAS DataBase Reference)
EPA Substance Registry System
Isoeugenol (97-54-1)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38-43
Safety Statements 
26-36-36/37-24/25
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
2
RTECS 
SL7875000
TSCA 
Yes
HS Code 
29095000
Toxicity
LD50 orally in rats: 1560 mg/kg (Jenner)

MSDS

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ISOEUGENOL Usage And Synthesis

Description

Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol existing in some essential oils of plants. It is produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. It can also be used as inhibitors of lipid peroxidation and as free radicals scavenger. Because of its antimicrobial properties as well as pleasing aromas and flavors, humans, since antiquity, have used plant material containing phenylpropenes to preserve and flavor their food.

References

Koeduka, Takao, et al. "Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester." Proceedings of the National Academy of Sciences 103.26 (2006): 10128-10133.
Rajakumar, D. V., and M. N. A. Rao. "Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers." Biochemical pharmacology 46.11 (1993): 2067-2072.

Description

Isoeugenol has a floral odor reminiscent of carnation. May be prepared by the alkaline isomerization of eugenol obtained from essential oils high in eugenol.

Chemical Properties

Isoeugenol has a floral odor reminiscent of carnation.

Chemical Properties

light yellow-green viscous liquid

Chemical Properties

Isoeugenol occurs in many essential oils, mostly with eugenol, but not as the main component. Commercial isoeugenol is a mixture of (E)- and (Z)-isomers, in which the (E)-isomer dominates because it is thermodynamically more stable. Isoeugenol is a yellowish, viscous liquid with a fine clove odor, with that of the crystalline trans-isomer being the more delicate.
Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin was formerly prepared by oxidation of isoeugenol. Additional fragrance materials are prepared by esterification or etherification of the hydroxy group.
Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin was formerly prepared by oxidation of isoeugenol. Additional fragrance materials are prepared by esterification or etherification of the hydroxy group.

Occurrence

The commercial product is a mixture of cis- and trans-isomers; reported found in the essential oils of ylangylang and nutmeg; also in the oil from flowers of Michelia champaca and in the oil from seeds of Nectandra puchury. Reported found in bilberry, guava, blackberry, tomato, cinnamon, clove bud and stem, nutmeg, mace, thymus, tea, coffee, fatty fish, beer, rum, plum, mushroom, dill, malt wort, elder flower, cuttlefish, Chinese quince, pimento leaf and maté.

Uses

isoeugenol is a volatile oil fraction derived from eugenol. It is also found in ylang-ylang and nutmeg oils. It is used in cosmetics as a fragrance or to mask odor.

Preparation

The starting material for the synthesis of isoeugenol is eugenol.The sodium or potassium salt of eugenol is isomerized to isoeugenol by heating. Isomerization can also be achieved catalytically in the presence of ruthenium [346] or rhodium compounds.

Definition

ChEBI: A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group.

Aroma threshold values

Detection: 100 ppb

Taste threshold values

Taste characteristics at 10 ppm: sweet spice and clove with woody and phenolic nuances.

General Description

Pale yellow oily liquid with a spice-clove odor. Freezes at 14°F. Density 1.08 g / cm3. Occurs in ylang-ylang oil and other essential oils.

Air & Water Reactions

Slightly water soluble .

Fire Hazard

ISOEUGENOL is combustible.

Contact allergens

Isoeugenol is a mixture of two cis and trans isomers. It occurs in ylang-ylang and other essential oils. It is a common allergen of perfumes and cosmetics such as deodorants and is contained in fragrance mix. Its presence in cosmetics is indicated in the INGREDIENTS series. Substitution by esters such as isoeugenyl acetate (not indicated on the package) does not always resolve the allergenic problem, because of the in vivo hydrolysis of the substitute into isoeugenol.

Chemical Synthesis

By the alkaline isomerization of eugenol obtained from essential oils high in eugenol.

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ISOEUGENOLSupplierMore

J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
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jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
21-61259100-
Email:
sh@meryer.com
Chembest Research Laboratories Limited
Tel:
021-20908456-
Email:
sales@BioChemBest.com
Alfa Aesar
Tel:
400-610-6006; 021-67582000
Email:
saleschina@alfa-asia.com
TCI (Shanghai) Development Co., Ltd.
Tel:
021-67121386 / 800-988-0390
Email:
Sales-CN@TCIchemicals.com
Basic information Description References Safety Related Supplier