ISOEUGENOL Property

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. 

-20°C

solubility 

Benzene (Slightly), Chloroform, Methanol (Sparingly)

pka

10.10±0.31(Predicted)

form 

Viscous Liquid

color 

Clear yellow

Odor

at 100.00 %. sweet spicy clove woody allspice carnation floral

Odor Type

spicy

Merck 

14,5171

JECFA Number

1260

BRN 

1909602

Stability:

Stable. Incompatible with strong oxidizing agents.

LogP

2.48

CAS DataBase Reference

97-54-1(CAS DataBase Reference)

EPA Substance Registry System

Isoeugenol (97-54-1)

Safety

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

Hazardous Substances Data

97-54-1(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1560 mg/kg (Jenner)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ISOEUGENOL Chemical Properties,Usage,Production

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.

Uses

Isoeugenol is used inmanufacture of vanillin; perfumes; flavoring; fragrance in perfumery, over-the-counter medicines, dental materials, foods; some perfumery uses (soap gardenia; coffee; abronea; tuberose; jonquil); natural occurrence (nutmeg oil).

Uses

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).

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.

Synthesis

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