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2-Methoxy-4-methylphenol

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2-Methoxy-4-methylphenol Basic information
Product Name:2-Methoxy-4-methylphenol
Synonyms:4-hydroxy-3-methoxy-1-methyl-benzene;4-HYDROXY-3-METHOXYTOLUENE;4-METHYLCATECHOL 2-METHYL ETHER;4-METHYLGUAJACOL;1-HYDROXY-2-METHOXY-4-METHYLBENZENE;2-2-Methoxy-4-methylphenol;2-Methoxy-4-methylphenol≥ 99% (GC);2-Methoxy-4-methylphenol 93-51-6 with low price CAS NO.93-51-6
CAS:93-51-6
MF:C8H10O2
MW:138.16
EINECS:202-252-9
Product Categories:Pyridines ,Halogenated Heterocycles;Pharmaceutical Raw Materials;API intermediates;bc0001
Mol File:93-51-6.mol
2-Methoxy-4-methylphenol Structure
2-Methoxy-4-methylphenol Chemical Properties
Melting point 5 °C (lit.)
Boiling point 221-222 °C (lit.)
density 1.092 g/mL at 25 °C (lit.)
FEMA 2671 | 2-METHOXY-4-METHYLPHENOL
refractive index n20/D 1.537(lit.)
Fp 211 °F
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
pka10.27±0.18(Predicted)
form Liquid
color colorless to light yellow
Specific Gravity1.091.092
Odorat 10.00 % in dipropylene glycol. spicy clove vanilla phenolic medicinal leathery woody smoky burnt
Odor Typespicy
biological sourcesynthetic
Water Solubility Slightly soluble in water.
Merck 14,2571
JECFA Number715
BRN 1862340
Henry's Law Constant7.7×100 mol/(m3Pa) at 25℃, Sagebiel et al. (1992)
Dielectric constant11.0
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C8H10O2/c1-6-3-4-7(9)8(5-6)10-2/h3-5,9H,1-2H3
InChIKeyPETRWTHZSKVLRE-UHFFFAOYSA-N
SMILESCOc1cc(C)ccc1O
LogP1.65
CAS DataBase Reference93-51-6(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 2-methoxy-4-methyl-(93-51-6)
EPA Substance Registry SystemPhenol, 2-methoxy-4-methyl- (93-51-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36-24/25
RIDADR 2810
WGK Germany 3
RTECS GP1755000
10
TSCA TSCA listed
HazardClass 6.1(a)
PackingGroup II
HS Code 29095090
Storage Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
MSDS Information
ProviderLanguage
4-Hydroxy-3-methoxy-1-methyl-benzene English
ACROS English
SigmaAldrich English
ALFA English
2-Methoxy-4-methylphenol Usage And Synthesis
Description2-Methoxy-4-methylphenol has a characteristic aromatic odor (sweet, spicy, slightly vanilla-like) and a somewhat bitter taste (vanilla-like). May be prepared by methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.
Chemical Properties2-Methoxy-4-methylphenol is a clear colorless to slightly yellow liquid or viscous, yeelowish oil, solidifying in the cold. The prismatic crystals melt at 6° C. Sp.Gr. 1.10. B.P. 222° C. Very slightly soluble in water, soluble in alcohol and oils. Sweet-spicy, phenolic-leathery odor with distinctly Vanilla-1ike undertones, balsamicwarm sweetness, but overall too medicinal to become classified as a versatile, floral-balsamic ingredient.
OccurrenceOccurs in beechwood tar; also identified in the essential oils of ylang-ylang, jasmine and anise seeds; it is one of the active constituents of creosote. Reported found in Gruyere cheese, smoked fish, cured pork, beer, rum, bourbon whiskey, malt and Scotch whiskey, sherry, white and red wine, cocoa, coffee, tea, mushrooms, mango, pear brandy, malt, wort, dried bonito, Bourbon vanilla, cuttlefish and green maté.
Uses2-Methoxy-4-methylphenol is used for blending baking and smoked food flavors. Excellent additive and modifier in artificial Ylang-Ylang, Cassie-bases, Jasmin bases, Lily, Gardenia, etc. Finds use in flavor compositions for imitation Vanilla, Clove, various fruit compositions, Rum flavors, etc. and in Nut-Nougat flavor bases. Concentration will be about 0.02 to 1 ppm in the finished consumer product. In beverages, however, it may be as high as 10 to 20 ppm.
Production Methods With three distinct oxygenated functional groups (aldehyde, ether, and hydroxyl), VAN can undergo selective hydrodeoxygenation to produce 2- methoxy-4-methylphenol (MMP), a promising candidate for future biofuel applications and its use in fragrances and intermediate in pharmaceutical synthesis. Kumar et al. developed stable, cost-effective Ni nanoparticles supported on montmorillonite (MMT) clay, which was synthesized for eco-friendly, alcohol-mediated catalytic transfer hydrodeoxygenation of VAN to MMP. The Ni(10%)/MMT catalyst achieved >99% VAN conversion and 95.2% MMP selectivity using isopropanol (IPA) as a solvent and hydrogen donor[1].
References[1] Atul Kumar, Prof. Dr. Rajendra Srivastava, Dr. Rajaram Bal. “Ni Nanoparticles Supported Montmorillonite Clay for Selective Catalytic Transfer Hydrodeoxygenation of Vanillin into 2-Methoxy-4-methylphenol.” ChemCatChem 16 9 (2024).
DefinitionChEBI: 2-Methoxy-4-methylphenol is a member of phenols and a member of methoxybenzenes. It is used in preparation of renewable bis(cyanate) esters.
PreparationBy methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.
Aroma threshold valuesDetection: 90 ppb. Aroma characteristics at 1.0%: smoky, sweet, phenolic, vanilla, spicy clove with a floral carnation nuance.
Taste threshold valuesTaste characteristics at 1.0 to 1.25 ppm: sweet phenolic, spice, vanilla, medicinal, clove-like, smoky, guaia col-like with a woody, phenolic nuance.
General Description2-Methoxy-4-methylphenol is the major component of black-ripe table olive aroma. It is the major anti-inflammatory compound in bamboo vinegar. Kinetics of reaction of 2-methoxy-4-methylphenol with chlorine atoms was studied.
Biochem/physiol ActionsOdor at 1.0%
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