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ISOEUGENOL

CAS No.
97-54-1
Chemical Name:
ISOEUGENOL
Synonyms
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenol;2-METHOXY-4-PROPENYLPHENOL;Phenol, 2-methoxy-4-propenyl-;2-methoxy-4-(1-propenyl)-Phenol;Phenol,2-methoxy-4-(1-propen-1-yl)-;FEMA 2468;ISOEUGENOL;NCI-C60979;Isoeugenol,c&t;ISOEUGENOL 6504
CBNumber:
CB8133429
Molecular Formula:
C10H12O2
Molecular Weight:
164.2
MDL Number:
MFCD00009285
MOL File:
97-54-1.mol
MSDS File:
SDS
Last updated:2024-04-16 18:29:06

ISOEUGENOL 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)
FEMA 2468 | ISOEUGENOL
refractive index n20/D 1.575(lit.)
Flash point >230 °F
storage temp. -20°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
Odor Type spicy
Merck 14,5171
JECFA Number 1260
BRN 1909602
Stability Stable. Incompatible with strong oxidizing agents.
LogP 2.48
Substances Added to Food (formerly EAFUS) ISOEUGENOL
FDA 21 CFR 172.515
CAS DataBase Reference 97-54-1(CAS DataBase Reference)
EWG's Food Scores 4-7
FDA UNII 5M0MWY797U
EPA Substance Registry System Isoeugenol (97-54-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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  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)
NFPA 704
2
2 0

ISOEUGENOL price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W246830 Isoeugenol natural, 99%, FG 97-54-1 1kg $193 2024-03-01 Buy
Sigma-Aldrich W246808 Isoeugenol mixture of cis and trans, 99%, FG 97-54-1 1kg $185 2024-03-01 Buy
Sigma-Aldrich W246808 Isoeugenol mixture of cis and trans, 99%, FG 97-54-1 10Kg $1280 2024-03-01 Buy
Sigma-Aldrich I17206 Isoeugenol 98%, mixture of cis and trans 97-54-1 5g $53.5 2024-03-01 Buy
Sigma-Aldrich CRM40158 Isoeugenol solution certified reference material, 2000?μg/mL in methanol, ampule of 1?mL 97-54-1 1mL $136 2024-03-01 Buy
Product number Packaging Price Buy
W246830 1kg $193 Buy
W246808 1kg $185 Buy
W246808 10Kg $1280 Buy
I17206 5g $53.5 Buy
CRM40158 1mL $136 Buy

ISOEUGENOL Chemical Properties,Uses,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 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.

Chemical Properties

light yellow-green viscous liquid

Chemical Properties

Isoeugenol has a floral odor reminiscent of carnation.

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 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 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 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).

Definition

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

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.

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.

97-53-0
97-54-1
Synthesis of ISOEUGENOL from Eugenol
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View Lastest Price from ISOEUGENOL manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
ISOEUGENOL pictures 2024-04-16 ISOEUGENOL
97-54-1
US $6.00 / KG 1KG 99% 2000KG/MONTH Hebei Saisier Technology Co., LTD
ISOEUGENOL pictures 2023-12-25 ISOEUGENOL
97-54-1
US $0.00 / kg 1kg 99% 1000000 Hebei Jingbo New Material Technology Co., Ltd
ISOEUGENOL pictures 2023-10-23 ISOEUGENOL
97-54-1
US $0.00-0.00 / kg 1kg 0.99 50000kg Hebei Yibangte Import and Export Co. , Ltd.
  • ISOEUGENOL pictures
  • ISOEUGENOL
    97-54-1
  • US $6.00 / KG
  • 99%
  • Hebei Saisier Technology Co., LTD
  • ISOEUGENOL pictures
  • ISOEUGENOL
    97-54-1
  • US $0.00 / kg
  • 99%
  • Hebei Jingbo New Material Technology Co., Ltd
  • ISOEUGENOL pictures
  • ISOEUGENOL
    97-54-1
  • US $0.00-0.00 / kg
  • 0.99
  • Hebei Yibangte Import and Export Co. , Ltd.
4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE 4-PROPENYL-2-METHOXYPHENOL 4-PROPENYLGUAIACOL 3-METHOXY-4-HYDROXYPROPENYLBENZENE 2-METHOXY-4-((E)-PROPENYL)-PHENOL FEMA 2468 ISOEUGENOL ISOEUGENOL 6504 PHENOL, 2-METHOXY-4-(1-PROPENYL) PROPENYLGUAIACOL 4-Hydroxy-3-methoxypropenylbenzene 5-Propenylguaiacol Isoeugenol,c&t isoeugenol,mixtureofcis/transisomers NCI-C60979 1-Hydroxy-2-methoxy-4-propenylbenzene 2-methoxy-4-(1-propenyl)-pheno 2-Methoxy-4-(1-propenyl)phenol 2-Methoxy-4-[(1E)-1-propenyl]phenol 2-methoxy-4-propenyl-pheno 2-Methoxy-4-propenylphenol (isoeugenol) ISOEUGENOL (CIS+TRANS) ISOEUGENOL MIXTURE CIS AND TRANS Isoeugenol, Oekanal ISOEUGENOL, 98%, MIXTURE OF CIS AND TRAN S Isoeugenol,cis+trans,97% 2-Methoxy-4-(prop-1-en-1-yl) isoeugenol,2-methoxy-4-propenylphenol 2-methoxy-4-[(E)-prop-1-enyl]phenol ISOEUGENOL(CIS AND TRANS MIX)(P) Phenol,2-methoxy-4-(1-prop ISOEUGENOL WITH GC Isoeugenol, cis + trans, 98+% Isoeugenol (cis- and trans- mixture) bis-2-Methoxy-4-propenylphenol Isoeugenol, 99%, mixture of cis/trans isomers Isoeugenol (Z+E) Isoeugenol 1g [97-54-1] Isoeugenol  4-Hydroxy-3-methoxy-1-propenylbenzene Propenylguaiacol Isoeugenol (Mixture of IsoMers) ISOEUGENOL FOR SYNTHESIS 100 ML Isoeugenol, Mixture of cis and trans ISOEUGENOL ISO 9001:2015 REACH ISOEUGENOL(97-54-1) Isoeugenol (mixture of cis and trans) pure, 98% Isoeugenol, 97%, mixture of cis and trans ISOEUGENOL SOLUTION Eugenol Impurity 17(Isoeugenol)(mixture of cis and trans isomers) Isoeugenol 97-54-1 kf-wang(at)kf-chem.com Factory supply Isoeugenol 97-54-1 kf-wang(at)kf-chem.com Isoeugenol(cis-andtrans-mixture)> Isoeugenol1000 μg/mL in Ethanol 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol 2-METHOXY-4-PROPENYLPHENOL 2-methoxy-4-(1-propenyl)-Phenol (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol Phenol,2-methoxy-4-(1-propen-1-yl)-