Basic information
- CAS
97-54-1- Standard SMILES
CC=Cc1ccc(O)c(OC)c1- InChIKey
BJIOGJUNALELMI-UHFFFAOYSA-N- Molecular formula
- C10H12O2
- Average molar mass
- 164.2 g/mol
- Monoisotopic mass
- 164.08372962
Overview
Isoeugenol is a commonly used fragrance added to many commercially available products, and occurs naturally in the essential oils of plants such as ylang-ylang. It is also a significant dermatologic sensitizer and allergen, and as a result has been restricted to 200 p.p.m. since 1998 according to guidelines issued by the fragrance industry. Allergic reactivity to Isoeugenol may be identified with a patch test.
Names & identifiers
- Preferred name
- Propenylguaiacol
- IUPAC
- 2-methoxy-4-prop-1-enylphenol
- English name
- ISOEUGENOL
- Molecular formula
- C10H12O2
- Molecular weight
- 164.2
Names & synonyms
PropenylguaiacolIsoeugenol (cis- and trans- mixture)2-methoxy-4-prop-1-enylphenol2-methoxy-4-propenyl-PhenolPhenol, 2-methoxy-4-(propenyl)-2-methoxy-4-prop-1-enyl-phenolEugenol Impurity 21Phenol,2-methoxy-4-(1E)-1-propen-1-yl-4-propenyl-2-methoxyphenolCIS/TRANS-ISOEUGENOLSCHEMBL57987SCHEMBL58288
Show more names
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenolFEMA 24682-METHOXY-4-PROPENYLPHENOLPhenol, 2-methoxy-4-propenyl-2-methoxy-4-(1-propenyl)-PhenolPHENOL, 2-METHOXY-4-(1-PROPENYL)Phenol,2-methoxy-4-(1-propen-1-yl)-ISOEUGENOLNCI-C60979
Isoeugenol,predominantly transorb1221628orb1304698SCHEMBL5961702CHEMBL2135887SCHEMBL10613593SCHEMBL11609326SCHEMBL18277295
Database identifiers
- CAS
97-54-1
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 154
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Physicochemical properties
- Melting point
- 10 °C · −10 °C (14 °F; 263 K)
- Boiling point
- 266 °C · 266 °C (511 °F; 539 K)
- Density
- 1.08 · 1.080
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.01 mm · <0.01 mm Hg ( 20 °C)
- FEMA
- 2468 · 2468 | ISOEUGENOL
- refractive index
- 1.58 · 1.58
- FLAVIS Number
- 4.004 · 04.004 | Isoeugenol
- Flash point
- 134 °C · 134 °C
- storage temp.
- -20 °C · -20°C
- solubility
- Benzene (Slightly), Chloroform, Methanol (Sparingly)
- pka
- 10.1 · 10.10±0.31(Predicted)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SL7875000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29095000
- Toxicity
- LD50 orally in rats: 1560 mg/kg (Jenner)
- risk_code
- 22-36/37/38-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36-36/37-24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302+H312-H315-H317-H319-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1ASTOT SE 3
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
- Hazardous Substances Data
- 97-54-1(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionIsoeugenol 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.
DescriptionIsoeugenol has a floral odor reminiscent of carnation. May be prepared by the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
OccurrenceThe 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.
Usesisoeugenol 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.
UsesIsoeugenol 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).
UsesIsoeugenol 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).
General DescriptionPale 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.
Preparation methods
PreparationThe 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.
Related reactions
18 records
Compound notes
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