| Identification | More | [Name]
ISOEUGENOL | [CAS]
97-54-1 | [Synonyms]
2-METHOXY-4-((E)-PROPENYL)-PHENOL
2-METHOXY-4-PROPENYLPHENOL
3-METHOXY-4-HYDROXYPROPENYLBENZENE
4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE
4-PROPENYL-2-METHOXYPHENOL
4-PROPENYLGUAIACOL
FEMA 2468
ISOEUGENOL
ISOEUGENOL 6504
PHENOL, 2-METHOXY-4-(1-PROPENYL)
PROPENYLGUAIACOL
1-Hydroxy-2-methoxy-4-propenylbenzene
2-methoxy-4-(1-propenyl)-pheno
2-Methoxy-4-(1-propenyl)phenol
2-methoxy-4-(1-propenyl)-Phenol
2-Methoxy-4-[(1E)-1-propenyl]phenol
2-methoxy-4-propenyl-pheno
2-Methoxy-4-propenylphenol (isoeugenol)
4-Hydroxy-3-methoxypropenylbenzene
5-Propenylguaiacol | [EINECS(EC#)]
202-590-7 | [Molecular Formula]
C10H12O2 | [MDL Number]
MFCD00009285 | [Molecular Weight]
164.2 | [MOL File]
97-54-1.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow-green viscous liquid | [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)
| [FEMA ]
2468 | [refractive index ]
n20/D 1.575(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
0-6°C | [solubility ]
Benzene (Slightly), Chloroform, Methanol (Sparingly) | [form ]
Viscous Liquid | [pka]
10.10±0.31(Predicted) | [color ]
Clear yellow | [Odor]
at 100.00 %. sweet spicy clove woody allspice carnation floral | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [biological source]
synthetic | [Odor Type]
spicy | [JECFA Number]
1260 | [Merck ]
14,5171 | [BRN ]
1909602 | [Henry's Law Constant]
2.7×100 mol/(m3Pa) at 25℃, HSDB (2015) | [Major Application]
cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care | [Cosmetics Ingredients Functions]
FLAVOURING
PERFUMING | [InChI]
1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ | [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. | [InChIKey]
BJIOGJUNALELMI-ONEGZZNKSA-N | [SMILES]
OC1=CC=C(/C=C/C)C=C1OC | [LogP]
2.48 | [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. | [CAS DataBase Reference]
97-54-1(CAS DataBase Reference) | [EPA Substance Registry System]
Isoeugenol (97-54-1) |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow-green viscous liquid | [Definition]
ChEBI: A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group. | [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]
This chemical is combustible. | [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.
| [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. | [Aroma threshold values]
Detection: 100 ppb | [Taste threshold values]
Taste characteristics at 10 ppm: sweet spice and clove with woody and phenolic nuances. | [Synthesis]
By the alkaline isomerization of eugenol obtained from essential oils high in eugenol. |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302+H312-H315-H317-H319-H335 | [Precautionary statements ]
P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
2
| [RTECS ]
SL7875000
| [TSCA ]
Yes | [HS Code ]
29095000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1A
STOT SE 3 | [Hazardous Substances Data]
97-54-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1560 mg/kg (Jenner) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Potassium hydroxide solution-->Eugenol-->Alkali Metals, plasma standard solution, Specpure, Ba,Be,Ca,Cs,K,Li,Mg,Na,Rb,Sr, 100μg/ml-->Safrole-->ISOAMYL ALCOHOL-->ISOSAFROLE-->Ylang Ylang Oil-->Mace oil-->Phenol, 4-[4-(dibutylamino)butyl]-2-methoxy--->Dibutylamine-->2-methoxy-4-prop-1-enylphenetole-->PROPENYL GUAETHOL | [Preparation Products]
Ethyl vanillin-->1-Benzyloxy-2-methoxy-4-propenylbenzene-->1-Acetoxy-2-methoxy-4-(1-propenyl)benzene-->Methyl isoeugenol-->2,6-Dimethoxyphenol-->Dihydroeugenol-->4-Propylphenol-->4-Hydroxy-3-methoxyphenylacetone-->Vanillic acid |
| Questions And Answer | Back Directory | [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.
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