2-methoxy-4-(prop-2-en-1-yl)phenol

• ChemBase ID: 103251
• Molecular Formular: C10H12O2
• Molecular Mass: 164.20108
• Monoisotopic Mass: 164.08372962
• SMILES: COc1c(O)ccc(CC=C)c1
• Canonical SMILES: C=CCc1ccc(c(c1)OC)O
• InChI: InChI=1S/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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxy-4-(prop-2-en-1-yl)phenol
• IUPAC Traditional name: eugenol; 2-methoxy-4-(prop-2-en-1-yl)phenol
• Synonyms: Eugenol; Eugenic acid; Caryophyllic acid; 1-Allyl-3-methoxy-4-hydroxybenzene; Allylguaiacol; 2-Methoxy-4-allylphenol; 4-Allylcatechol-2-methyl ether; 2-methoxy-4-(2-propen-1-yl)phenol; 4-allyl-2-methoxyphenol; 2-Methoxy-4-(2-propenyl)phenol; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; EUGENOL; 4-Allyl-1-Hydroxy-2-Methoxy Benzene; Eugenolum; 1-Allyl-4-hydroxy-3-methoxybenzene; 5-Allylguaiacol; 2-甲氧基-4-(2-丙烯基)苯酚; 4-烯丙基-2-甲氧基苯酚; 4-烯丙基愈创木酚; 丁子香酚; 丁香酚; 丁香酚

Database IDs

• CAS Number: 97-53-0
• EC Number: 202-589-1
• MDL Number: MFCD00008654
• Beilstein Number: 1366759
• Merck Index: 143898
• PubChem SID: 24894609; 162103090; 24862128; 24901115; 24869841; 24901114
• PubChem CID: 3314
• CHEBI ID: 4917
• CHEMBL: 42710
• Chemspider ID: 13876103
• FEMA ID: 2467
• KEGG ID: D04117
• Unique Ingredient Identifier: 3T8H1794QW
• Wikipedia Title: Eugenol
• Council of Europe Number: 171
• Flavis Number: 4.003

CALCULATED PROPERTIES

• Acid pKa: 9.941818
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.6105645
• LogD (pH = 7.4): 2.6093426
• Log P: 2.61058
• Molar Refractivity: 48.7894 cm^3
• Polarizability: 18.73316 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -10°C; -12 to -10°C; -12--10 °C(lit.); -7.5°C
• Boiling Point: 252-253°C; 254 °C(lit.); 254°C
• Flash Point: >230°C; 104 °C; 112 °C; 127°C(260°F); 233.6 °F
• Density: 1.06 g/cm^3; 1.067 g/mL at 25 °C(lit.); 1.068; 1.07 g/ml
• Refractive Index: 1.5410; n20/D 1.541(lit.)
• Vapor Pressure: 1 mm Hg at 78.4 °C
• pKa: 10.19 at 25 °C
• Organoleptic: cinnamon; clove; spicy

Safety Information

• Storage Condition: Room Temperature (15-30°C); Room Temperature (15-30°C), Protect from light
• RTECS: SJ4375000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1; 3
• Risk Statements: 22-36/37/38-42/43; 22-36/38-43; R:22
• Safety Statements: 23-24-26-37; 26-36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H317; H302-H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (177.2800); FDA 21 CFR (184.1257)

Pharmacology Properties

• Gene Information: human ... UGT1A4(54657)
• Allergens: no known allergens
• Mechanism of Action: Thromboxane antagonist

Product Information

• Purity: ~99%; ≥98%; 99%
• Grade: FG; Halal; Kosher; natural; NI; PESTANAL®, analytical standard; Ph Eur; ReagentPlus®
• Biological Source: Very widespread occurrence in essential oils. Major component of clove oil. Also found in those of Cinnamomum spp., Cistus spp., Camellia spp., Pelargonium spp., Thymus spp. and Citans peel spp. Present in apple, apricot, banana and cherry fruits
• Application(s): Antifungal agent; Antioxidant; Antiseptic; Dental analgesic
• Linear Formula: 4-(H2C=CHCH2)C6H3-2-(OCH3)OH

DETAILS

MP Biomedicals - 02151106

1 ml = approx. 1.07 gm
Colorless to light yellow liquid
Purity: ~99%

MP Biomedicals - 02151107

Reportedly used as internal standard in GC assays of biological samples for presence of thymol.
1 ml = approx. 1.07 gm
Anal. Biochem., 69, 10 (1975).

Sigma Aldrich - E51791

Packaging
5, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - W246719

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - W246700

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - 35995

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 1091A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 278A, (nmr)
• Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1028A, (ir)
• Erdmann, F. et al., J. Prakt. Chem., 1897, 56, 143, (synth)
• Naves, Y.-R., Helv. Chim. Acta, 1948, 31, 378, (isol)
• Psenak, M. et al., Planta Med., 1970, 19, 154, (Gein)
• Popa, G. et al., Rev. Chim. (Bucharest), 1973, 24, 635; CA, 80, 103486u
• Manito, P. et al., J.C.S. Perkin 1, 1974, 1727; 1975, 1548, (biosynth)
• Khischies, M. et al., Chem. Comm., 1975, 879, (biosynth)
• Yamaguchi, H. et al., Chem. Pharm. Bull., 1975, 23, 1169, (pmr)
• Opdyke, D.L.J., Food Cosmet. Toxicol., 1975, 13, 545, (rev, tox)
• Massow, F. et al., J.C.S. Perkin 2, 1976, 977, (cmr)
• Bohlmann, F. et al., Phytochemistry, 1976, 15, 1318, (isol)
• Shibuya, M. et al., Chem. Pharm. Bull., 1978, 26, 2671, (deriv)
• Wenkert, E. et al., Synthesis, 1983, 701, (synth)
• IARC Monog., 1985, 36, 75; Suppl., 7, 63, (rev, tox)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EQR500; EQS000