Isoeugenol

Cosmetics ingredient -> Base; Flavor; Fragrance; Other (Specify)

Masking

log Kow = 3.04

3.04

3.04

1.08 at 77 °F (NTP, 1992) - Denser than water; will sink

1.080 g/cu cm at 25 °C

1.079-1.085

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1995) of reports.

Warning

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Phenol, 2-methoxy-4-(1-propenyl)-

Chemical: Phenol, 2-methoxy-4-(1-propenyl)-, (E)-

Hazard Traits - Carcinogenicity; Fragrance Allergen

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Phenol, 2-methoxy-4-(1-propen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-methoxy-4-(1-propen-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 23-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/18867

IMAP assessments - Isoeugenol and its constituent isomers: Human health tier II assessment

IMAP assessments - Isoeugenol and its constituent isomers: Human health tier II assessment

An irritant; Possible sensitizer; [MSDSonline] Isoeugenol is a fragrance allergen that causes allergic contact dermatitis. [Marks, p. 168, 172] Danger of skin sensitization; [MAK] Common allergen in cosmetics and perfumes; [Kanerva, p. 1805] See Eugenol.

Isoeugenol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Acute Tox. 4 (99.5%)

Acute Tox. 4 (97.4%)

Acute toxicity (ingestion) - category 4

Acute toxicity (ingestion) - category 4

Acute toxicity (Oral) - Category 4

Skin Sens. 1A

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 680(SRC), determined from a structure estimation method(2), indicates that isoeugenol is expected to have low mobility in soil(SRC). Volatilization of isoeugenol from moist soil surfaces is expected to occur(SRC) given an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 0.0135 mm Hg at 25 °C(3), and water solubility, 810 mg/L(4). Isoeugenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Isoeugenol was found to be readily biodegradable using a Manometric Respirometry Test in which isoeugenol reached 79% biodegradation after 28 days(4); the biodegradation started on day 2 and reached 79% at the end of the 10-day window period(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 680(SRC), determined from a structure estimation method(2), indicates that isoeugenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0135 mm Hg at 25 °C(4), and water solubility, 810(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 13 and 100 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 47(SRC), from its log Kow and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Isoeugenol is degraded in natural water by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in water is estimated to be 20.6 days(SRC), calculated from its rate constant of 3.9X10+10 L/mol-sec(7). Isoeugenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isoeugenol, which has an extrapolated vapor pressure of 0.0135 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isoeugenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.3 hours(SRC), calculated from its rate constant of 8.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase isoeugenol is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 3 hours(SRC), calculated from its rate constant of 1X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Isoeugenol was detected in the skin and pulp of Queen Anne's pocket melon (Cucumis melo var dudaim (L.) Naudin) at respective concentrations of 25.4 mg/kg and 2.7 mg/kg(1). Isoeugenol was identified as an odorant component of ginger oil(2).

Isoeugenol concentrations in various plants(1).[Table#8033]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=97-54-1]

Two condensate effluents generated at a Canadian mill involved with bleached softwood pulp production contained isoeugenol concentrations of 10 ng/mL and 121 ng/mL(1). Isoeugenol was detected in 6 effluents collected from 13 paper and pulp in Quebec Canada in 1990 at a concentration of 0 (detection limit not specified) to 28643 ug/L(2). The emission rate of isoeugenol in wood smoke from the combustion of oak, eucalyptus and pine wood was reported as 1.0, 0.5 and 17 ug/g respectively(3). The emission rate of isoeugenol in wood smoke from the combustion of pine wood logs, oak wood logs and synthetic logs was reported as 8.04 mg/kg, 0.16 mg/kg and not detected respectively(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of isoeugenol can be estimated to be 680(SRC). According to a classification scheme(2), this estimated Koc value suggests that isoeugenol is expected to have low mobility in soil.

Isoeugenol occurs in ylang-ylang and other essential oils(1). Isoeugenol was detected in the skin and pulp of Queen Anne's pocket melon (Cucumis melo var dudaim L. Naudin)(2). Isoeugenol was identified as an odorant component of ginger oil(3). Isoeugenol was identified as an emission component in wood smoke from the combustion of wood(4,5).

/HUMAN EXPOSURE STUDIES/ The potential of isoeugenol, an important fragrance and flavor ingredient, to induce delayed contact hypersensitivity or to elicit pre-existing sensitization reactions in man was evaluated by analyzing patch-test data from dermatitic and non-dermatitic subjects. Results from a total of 6512 patch tests (involving approximately 5850 subjects) on isoeugenol alone and on various consumer products and fragrance blends containing isoeugenol, were collected from fragrance and formulator companies. Hypersensitivity induced by isoeugenol was concentration dependent. All but two of the reactions occurring in this survey were at exposure concentrations greater than or equal to 0.8% isoeugenol. No induced reactions occurred in the 1004 patch tests reported at isoeugenol concentrations between 0.03 and 0.5%. One induced reaction in 32 patch tests was attributable to isoeugenol at a concentration of 0.02% while another induced reaction in 23 patch tests conducted at the same concentration was resolved to an isoeugenol-eugenol mixture. One elicited reaction at an isoeugenol concentration of 0.04% occurred in the 6512 patch tests reported in this survey. This single elicitation was resolved to an isoeugenol-eugenol mixture, but the specific causative agent was not identified. The results of this survey indicate that isoeugenol has a very low potential for either eliciting pre-existing sensitization reactions ('elicited' reactions) or inducing hypersensitivity ('induced' reactions) in subjects exposed to consumer products containing this ingredient.

/HUMAN EXPOSURE STUDIES/ The elicitation response in allergic contact dermatitis is dose dependent, but the time-concentration relationship for elicitation has not previously been described. In this study 27 isoeugenol-sensitive patients participated in serial dilution patch tests with isoeugenol and a double-blinded Repeated Open Application Test (ROAT) using two concentrations of isoeugenol, 0.2 and 0.05%. Seven controls without isoeugenol allergy were also included. The participants applied 3.72 +/- 1.57 (mean +/- SD) mg/sq cm of coded isoeugenol solutions twice a day to a 3 x 3 sq cm area on the volar aspect of the right and left arm, respectively. For each test site the applications continued until a reaction appeared or for a maximum of 28 days. The minimal criteria for a positive reaction regarded as allergic contact dermatitis was persistent erythema at the ROAT test site. All controls were negative and 16/24 (66.7%) of the included isoeugenol-sensitive subjects showed a positive ROAT to the 0.2% solution within the study period (Fisher's test, p = 0.0024). Ten of the positive patients also reacted to the 0.05% solution. The median number of days until a positive reaction to the 0.2% solution was 7 days and was 15 days for the 0.05% solution. There was a highly significant correlation between the patients' patch test threshold and the number of days until a positive ROAT. In conclusion, the time until an isoeugenol allergic individual reacts in a ROAT depends on the individual sensitivity as well as the exposure concentrations; for low concentrations of the allergen or low degree of sensitivity, the allergic contact dermatitis may develop after several weeks of exposure. Therefore, a negative ROAT after 7 days may be a false negative.

/HUMAN EXPOSURE STUDIES/ Axillary dermatitis is common and overrepresented in people with contact allergy to fragrances. Many people suspect their deodorants to be the incriminating products. In order to investigate the significance of isoeugenol in deodorants for the development of axillary dermatitis when used by people with and without contact allergy to isoeugenol, patch tests with deodorants and ethanol solutions with isoeugenol, as well as repeated open application tests (ROAT) with roll-on deodorants with and without isoeugenol at various concentrations, were performed in 35 dermatitis patients, 10 without and 25 with contact allergy to isoeugenol. A positive ROAT was observed only in patients hypersensitive to isoeugenol (P<0.001) and only in the axilla to which the deodorants containing isoeugenol had been applied (P<0.001). Deodorants containing isoeugenol in the concentration range of 0.0063-0.2% used 2 times daily on healthy skin can thus elicit axillary dermatitis within a few weeks in people with contact allergy to isoeugenol.

/HUMAN EXPOSURE STUDIES/ ... During a five-year period 3,065 patients with contact dermatitis were patch tested using a specific mix of fragrances. 509 (16.6%) patients were allergic to the fragrance mix, while 258 (8.4%) patients exhibited an allergic reaction to Myroxylon pereirae (balsam of Peru). Between those 509 patients, 157 were patch tested with eight individual substances contained in the fragrance mix: cinnamal, cinnamyl alcohol, eugenol, isoeugenol, geraniol, hydroxycitronellal, alpha-amyl cinnamal and Evernia prunastri (oak moss). The most frequent allergens were isoeugenol 57.9% (91/157), eugenol 55.4% (87/157), cinnamyl alcohol 34.4% (54/157) and Evernia prunastri (oak moss) 24.2% (38/157). ...

Isoeugenol's production and use as a fragrance in household laundry and cleaning products(1) and perfumes(2), as a flavoring agent and in the manufacture of vanillin(3) may result in its release to the environment through various waste streams(SRC). Its application as a fish anesthetic/sedative(4) will result in its direct release to the environment(SRC).

AEROBIC: Isoeugenol, at a concentration of 100 mg/L, was found to be readily biodegradable using a Manometric Respirometry Test (OECD Guideline 301F) in which isoeugenol reached 79% biodegradation after 28 days(1); the biodegradation started on day 2 and reached 79% at the end of the 10-day window period(1).

Isoeugenol

Group 2B: Possibly carcinogenic to humans

Volume 134: (2024) Aspartame, Methyleugenol, and Isoeugenol

2024 online

2023

Isoeugenol

An estimated BCF of 47 was calculated in fish for isoeugenol(SRC), using a log Kow of 3.04(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Isoeugenol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

/The investigators/ previously demonstrated in the human promyelocytic cell line THP-1 that all allergens tested, with the exception of the prohapten isoeugenol, induced a dose-related release of interleukin-8 (IL-8). .. The present study ... investigated whether this abnormal behavior was regulated by the AU-rich element-binding proteins HuR and tristetraprolin (TTP) or by the downstream molecule suppressor of cytokine signaling (SOCS)-3. The contact allergens isoeugenol, diethylmaleate (DEM), and 2,4-dinitrochlorobenzene (DNCB), and the irritant salicylic acid were used as reference compounds. Chemicals were used at concentrations that induced a 20% decrease in cell viability as assessed by propidium iodide staining, namely 100 ug/mL (0.61 mM) for isoeugenol, 100 ug/mL (0.58 mM) for DEM, 3 ug/mL (14.8 uM) for DNCB, and 250 ug/mL (1.81 mM) for salicylic acid. Time course experiments of IL-8 mRNA expression and assessment of IL-8 mRNA half-life, indicated a decreased IL-8 mRNA stability in isoeugenol-treated cells. We could demonstrate that a combination and regulation of HuR and TTP following exposure to contact allergens resulted in a different modulation of IL-8 mRNA half-life and release. The increased expression of TTP in THP-1 cells treated with isoeugenol results in destabilization of the IL-8 mRNA, which can account for the lack of IL-8 release. In contrast, the strong allergen DNCB failing to up-regulate TTP, while inducing HuR, resulted in longer IL-8 mRNA half-life and protein release. SOCS-3 was induced only in isoeugenol-treated cells; however, its modulation did not rescue the lack of IL-8 release, indicating that it is unlikely to be involved in the lack of IL-8 production. Finally, the destabilization effect of isoeugenol on IL-8 mRNA expression together with SOCS-3 expression resulted in an anti-inflammatory effect, as demonstrated by the ability of isoeugenol to modulate LPS or ionomycin-induced cytokine release.

Isoeugenol and its structural analog eugenol suppressed the lymphoproliferative response to concanavalin A stimulation in B6C3F1 mouse splenocyte cultures. Isoeugenol inhibited phorbol 12-myristate 13-acetate (PMA) plus ionomycin (Io)-induced IL-2 mRNA expression and protein secretion in B6C3F1 mouse splenocytes, and in EL4.IL-2 mouse T-cells, as determined by real-time RT-PCR and ELISA, respectively. To further characterize the inhibitory mechanism of isoeugenol at the transcriptional level, ... the DNA binding activity of the transcription factors for IL-2 using an electrophoretic mobility shift assay /was examined/. Isoeugenol decreased the binding activity of NF-AT and NF-kappaB in PMA/Io-stimulated EL4.IL-2 cells, but no significant effect was observed for AP-1 or Oct binding activity. Western blot analysis showed that isoeugenol also decreased the nuclear translocation of cytoplasmic NF-AT and NF-kappaB. These results suggest that isoeugenol suppresses IL-2 production through a decrease of IL-2 mRNA expression and that the inhibition is mediated, at least in part, through the down-regulation of NF-AT and NF-kappaB.

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 mediated via aryl hydrocarbon receptor (AhR) interactions. In this study the effects of eugenol and isoeugenol were determined on intracellular localization of AhR, AhR target gene expression, AhR-dependent cell cycle regulation, and proliferation in HaCaT cells. Both compounds produced a rapid and marked translocation of AhR into the nucleus, induced the expression of the AhR target genes cytochrome P-450 1A1 (CYP1A1) and AhR repressor (AhRR), and inhibited proliferation of HaCaT cells. Among the G(1) phase cell cycle-related proteins, levels of the retinoblastoma protein (RB), which is known to interact with AhR, and levels of the cyclin dependent kinase (CDK) 6 were reduced by eugenol and isoeugenol, whereas steady-state levels of CDK2 and CDK4 remained unaffected. Protein levels of CDK inhibitor (CKI) p27(KIP1), known to be modulated in an AhR-dependent manner, were increased after treatment with both substances. In conclusion, data show that the antiproliferative properties of eugenol and isoeugenol in HaCaT cells are mediated through AhR ... .

Effects of eugenol compounds on the production of nitric oxide (NO) in RAW264.7 macrophages were analyzed in relation to the anti-inflammatory action of these compounds. Eugenol and isoeugenol inhibited lipopolysaccharide (LPS)-dependent production of NO, which was due to the inhibition of protein synthesis of inducible nitric oxide synthase (iNOS). Isoeugenol showed the most effective inhibitory effect and eugenol was less effective. LPS-dependent expression of cyclooxygenase-2 (COX-2) protein was also inhibited markedly by isoeugenol, and less effectively by eugenol. Anti-inflammatory action of eugenol compounds may be explained by the inhibition of NO production and COX-2 expression, the pro-inflammatory mediators.

For more Mechanism of Action (Complete) data for Isoeugenol (8 total), please visit the HSDB record page.

Following a single oral dose of (14)C-isoeugenol (156 mg/kg, 50 uCi/kg), greater than 85% of the administered dose was excreted in the urine predominantly as sulfate or glucuronide metabolites by 72 hr. Approximately 10% was recovered in the feces, and less than 0.1% was recovered as CO(2) or expired organics. No parent isoeugenol was detected in the blood at any of the time points analyzed. Following iv administration (15.6 mg/kg, 100 uCi/kg), isoeugenol disappeared rapidly from the blood. The half life was 12 min and the Cl(s) was 1.9 L/min/kg. Excretion characteristics were similar to those of oral administration. The total amount of radioactivity remaining in selected tissues by 72 hr was less than 0.25% of the dose following either oral or intravenous administration. Results of these studies show that isoeugenol is rapidly metabolized and is excreted predominantly in the urine as phase II conjugates of the parent compound.

Trans-isoeugenol has known human metabolites that include trans-Isoeugenol-O-glucuronide.

5M0MWY797U

ISOEUGENOL

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Following a single oral dose of (14)C-isoeugenol (156 mg/kg, 50 uCi/kg), greater than 85% of the administered dose was excreted in the urine predominantly as sulfate or glucuronide metabolites by 72 hr. Approximately 10% was recovered in the feces, and less than 0.1% was recovered as CO(2) or expired organics. No parent isoeugenol was detected in the blood at any of the time points analyzed. Following iv administration (15.6 mg/kg, 100 uCi/kg), isoeugenol disappeared rapidly from the blood. The half life was 12 min and the Cl(s) was 1.9 L/min/kg. Excretion characteristics were similar to those of oral administration. The total amount of radioactivity remaining in selected tissues by 72 hr was less than 0.25% of the dose following either oral or intravenous administration. Results of these studies show that isoeugenol is rapidly metabolized and is excreted predominantly in the urine as phase II conjugates of the parent compound.

Occurs in ylang-ylang oil and other essential oils; [CAMEO] Used in perfumes, vanillin, and flavoring agents; [Hawley] Approved by the FDA as a food flavor; Used in cosmetics, medications, and dental materials; Occurs naturally in the oils of clove, ylang-ylang, tuberose, and jonquil; [Marks, p. 175]

Manufacture of vanillin.

Used as a fragrance in household laundry and cleaning products including, most notably, laundry powders (maximum concentration: 60 ppm), laundry liquids (maximum concentration: 70 ppm), dish-washing liquids (maximum concentration: less than 10 ppm), hard surface cleaning products (maximum concentration: 40 ppm) and toilet cleaning products (maximum concentration: less than 10 ppm)

Reported Uses:

Isoeugenol is used in perfumery in a large number of blossom compositions, mostly for clove and carnation types, but also in oriental perfumes. ... Small amounts are employed in aromas and in reconstituted essential oils.

AQUI-S is a fish anesthetic/sedative that is approved for use in a number of countries throughout the world and has the potential for use in the United States. The active ingredient in AQUI-S is isoeugenol.

2023: 8,258,684 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8034]

Isoeugenol

1-Hydroxy-2-methoxy-4-propen-1-ylbenzene; 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene; 4-Hydroxy-3-methoxy-1-propenylbenzene; iso-Eugenol; 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene; 2-Methoxy-4-propenylphenol; 2-Methoxy-4-(1-propenyl)phenol; Phenol, 2-methoxy-4-(1-propenyl)-; 4-Propenylguaiacol

IFRA_STD_048.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

From eugenol by isomerization with caustic potash.

The sodium or potassium salt of eugenol is isomerized to isoeugenol by heating. Isomerization can also be carried out catalytically in the presence of ruthenium or rhodium compounds.

Guaiacol is esterified with propionic acid, and the resulting guaiacyl propionate rearranges in the presence of aluminum chloride to give 4-hydroxy-3-methoxypropiophenone. Reduction of the ketone to the corresponding secondary alcohol and dehydration finally yield isoeugenol.

Cosmetics product ingredient: Isoeugenol (Phenol, 2-methoxy-4-(1-propenyl); (E)-2-methoxy-4-(prop-1-enyl)phenol; (trans-Isoeugenol); (Z)-2-methoxy-4-(prop-1-enyl)phenol; (cis-Isoeugenol))

Information on 89 consumer products that contain Isoeugenol in the following categories is provided:

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

All Other Chemical Product and Preparation Manufacturing

Phenol, 2-methoxy-4-(1-propen-1-yl)-: ACTIVE

Commercial isoeugenol is a mixture of cis- and trans-isomers, in which the trans-isomer dominates because it is thermodynamically more stable.

0.019 [Products applied to the lips]

0.0057 [Products applied to the axillae]

0.12 [Products applied to the face/body using fingertips]

0.11 [Products related to fine fragrances]

0.027 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.027 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]