Related Searches: eugenol, eugenol c10h12o2, methyl eugenol

Eugenol(CAS No. 97-53-0)

Eugenol C10H12O2 (cas 97-53-0) Molecular Structure

97-53-0 Structure

Identification and Related Records

【Name】
Eugenol
【CAS Registry number】
97-53-0
【Synonyms】
1,3,4-eugenol
1-Allyl-3-methoxy-4-hydroxybenzene
1-allyl-4-hydroxy-3-methoxybenzene
1-hydroxy-2-methoxy-4-allylbenzene
1-hydroxy-2-methoxy-4-prop-2-enylbenzene
1-hydroxy-2-methoxy-4-propenylbenzene
1-hydroxy-4-allyl-2-methoxybenzene
2-methoxy-1-hydroxy-4-allylbenzene
2-methoxy-4-(2-propen-1-yl)phenol
2-Methoxy-4-(2-propenyl)phenol
2-Methoxy-4-allylphenol
2-methoxy-4-prop-2-enylphenol
4-allyl-1-hydroxy-2-methoxybenzene
4-Allyl-2-methoxyphenol
4-allylcatechol-2-methyl ether
4-Allylguaiacol
p-eugenol
4-hydroxy-3-methoxyallylbenzene
5-allylguaiacol
Allylguaiacol
Caryophyllic acid
Eugenic acid
Eugenol Special
FA 100
fema no. 2467
【EINECS(EC#)】
202-589-1
【Molecular Formula】
C10H12O2 (Products with the same molecular formula)
【Molecular Weight】
164.2
【Inchi】
InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
【InChIKey】
RRAFCDWBNXTKKO-UHFFFAOYSA-N
【MOL File】
97-53-0.mol

Chemical and Physical Properties

【Appearance】
colourless to faintly yellow liquid with a strong odour of cloves
【Density】
1.066
【Melting Point】
-12--10℃
【Boiling Point】
254℃
【Refractive Index】
1.54-1.542
【Flash Point】
>230 ºF
【Water】
slightly soluble
【Solubilities】
Water Solubility :slightly soluble
【Color/Form】
Colorless or pale yellow liquid
CRYSTALS FROM HEXANE
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents.
【HS Code】
29095090
【Storage temp】
0-6°C
【Spectral properties】
INDEX OF REFRACTION: 1.5416 @ 19.5 DEG C/D; 1.5380-1.5420 @ 20 DEG C/D; SPECIFIC OPTICAL ROTATION: -1 DEG 30 MIN
Index of refraction: 1.5410 at 20 deg C/D
SADTLER REF NUMBER: 3880 (IR, PRISM)
IR: 5146 (Coblentz Society Spectral Collection)
UV: 3-254 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 260 (Varian Associates NMR Spectra Catalogue)
MASS: 77576 (NIST/EPA/MSDC Mass Spectral Data Base, 1990 Version)
【Computed Properties】
Molecular Weight:164.20108 [g/mol]
Molecular Formula:C10H12O2
XLogP3:2
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:3
Tautomer Count:3
Exact Mass:164.08373
MonoIsotopic Mass:164.08373
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Formal Charge:0
Complexity:145
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:9

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R22;R38
【Safety Statements 】
S24/25
【Formulations/Preparations】
Technical product contains 95-100% eugenol.
Grades: Technical, USP, FCC
【Exposure Standards and Regulations】
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Eugenol is included in analgesic and anesthetic drug products; fever blister and cold sore treatment drug products; poison ivy, poison oak, and poison sumac drug products; and astringent drug products.
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Eugenol is included on this list.
Zinc oxide-eugenol?(1) Identification. Zinc oxide-eugenol is a device composed of zinc oxide-eugenol intended to serve as a temporary tooth filling or as a base cement to affix a temporary tooth filling, to affix dental devices such as crowns or bridges, or to be applied to a tooth to protect the tooth pulp.
【Reactivities and Incompatibilities】
/Incompatible with/ ferric chloride, potassium permanganate.
【Octanol/Water Partition Coefficient】
log Kow = 2.27
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Oil containing eugenol ... treated with 3% aq solution of NaOH; nonacid components ... extracted with ether. Alkaline solution is acidified to isolate phenols and ... Fractionally distilled under reduced pressure. To avoid formation of emulsions, pretreatment of oil with tartaric acid ... preferred.
Obtained from many natural sources; ... from oil of cloves.
It can be extracted from clove oil with aqueous potassium hydroxide, followed by liberation with an acid, and distillation in a stream of CO2. It can be synthesized by the reaction of allyl chloride with guaiacol.
Eugenol is still preferentially isolated from clove leaf and cinnamon leaf oil (eg, by extraction with sodium hydroxide solution). Nonphenolic materials are them removed by steam distillation. After the alkaline solution is acidified at low temperature, pure eugenol is obtained by distillation.
U.S. Exports

(1984) 1.51X10+9 g /Citronellal, Eugenol, Geraniol, Heliotropin, Hydroxycitronellal and Isoeugenol/
U.S. Production

(1972) 2.15X10+8 g
(1975) 1.45X10+8 g
(1984) 1.63X10+8 g
Consumption Patterns

Eugenol is used primarily as a fragrance and flavoring agent, as an analgesic in dental materials and nonprescription drug products, as an insect attractant, and as a chemical intermediate. Several other applications have been reported, the commercial status of which is unknown. (1985)
【Usage】

In perfumery instead of oil of cloves, manufacture of vanillin, insect attractant.

Biomedical Effects and Toxicity

【Therapeutic Uses】
... Has been used as an antipyretic but it is relatively ineffective. /Eugenol/ has... been used in medicine for the study of mucous secretion /and/ gastric cytology, without gastric resection or gastroenterostomy. It has been shown to have anthelmintic properties. /SRP: Former use/
Nonprescription medicines for toothache commonly contain eugenol, and some products for canker-sore may do so also.
Eugenol is used as a component of several dental materials (e.g., dental cements, impression pastes and surgical pastes). Such products are principally combinations of zinc oxide and eugenol in varying ratios. They are reported to be widely used in dentistry as temporary filing materials, cavity liners for pulp protection, capping materials, temporary cementation of fixed protheses, impression materials and major ingredients of endodontic sealers. In addition, eugenol has been used in dentistry for disinfecting root canals.
Analgesic (dental)
【Biomedical Effects and Toxicity】
No absorption of eugenol occurred within 2 hr of application to intact shaved skin of mice. ... over 70% of an oral dose of eugenol was excreted in urine of rabbits.
Intraperitoneal injection of a single 450 mg/kg dose of (14)C methoxy labelled eugenol resulted in rapid distribution to all organs. Both ether- and water soluble materials were recovered from most tissues and excretions. Only 0.2-1.0% of the dose was eliminated as expired (14)CO2. Over 70% of a lethal dose of eugenol was recovered on death, from the urine of rabbits.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 409(SRC), determined from a log Kow of 2.27(2) and a regression-derived equation(3), indicates that eugenol is expected to have moderate mobility in soil(SRC). Volatilization of eugenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.26X10-2 mm Hg(4), and water solubility, 2,460 mg/L(5). Eugenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 409(SRC), determined from a log Kow of 2.27(2) and a regression-derived equation(3), indicates that eugenol 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 2.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.26X10-2 mm Hg(4), and water solubility, 2,463 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 24 and 177 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 31(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), eugenol, which has a vapor pressure of 2.26X10-2 mm Hg at 25 deg C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase eugenol 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 6 hours(SRC), calculated from its rate constant of 6.5X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of eugenol with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Eugenol does not absorb light at wavelengths >290 nm(5) and is not expected to be susceptible to direct photolysis by sunlight(SRC).

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