Propenylguaiacol

Base Information

• Chemical Name: Propenylguaiacol
• CAS No.: 97-54-1
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 29095000
• DSSTox Substance ID: DTXSID7022413
• Wikidata: Q420043
• ChEMBL ID: CHEMBL2135887
• Mol file: 97-54-1.mol

Synonyms:2-methoxy-4-prop-1-enylphenol;Propenylguaiacol;Phenol, 2-methoxy-4-(propenyl)-;CHEBI:18224;2-methoxy-4-propenyl-Phenol;DTXSID7022413;Epitope ID:114092;4-propenyl-2-methoxyphenol;CIS/TRANS-ISOEUGENOL;4-isopropenyl-2-methoxy-phenol;CHEMBL2135887;AKOS028108450;Isoeugenol 2000 microg/mL in Acetonitrile;4-hydroxy-3-methoxy-1-propen-1-yl benzene;FT-0627411;Q420043

Chemical Property of Propenylguaiacol

Chemical Property:

• Appearance/Colour: light yellow-green viscous liquid
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: -10 °C
• Refractive Index: n20/D 1.575(lit.)
• Boiling Point: 266.64 °C at 760 mmHg
• PKA: 10.10±0.31(Predicted)
• Flash Point: 122.907 °C
• PSA: 29.46000
• Density: 1.074 g/cm³
• LogP: 2.43390
• Storage Temp.: 0-6°C
• Solubility.: Benzene (Slightly), Chloroform, Methanol (Sparingly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 154

Purity/Quality:

98% ^*data from raw suppliers

Isoeugenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC(=C(C=C1)O)OC
• 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. Isoeugenol has a floral odor reminiscent of carnation. May be prepared by the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
• 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). 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). 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.

Technology Process of Propenylguaiacol

There total 86 articles about Propenylguaiacol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 19.3%

3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan (95316-34-0) → 2-methoxy-4-n-propylphenol (2785-87-7) + 2-methoxy-4-propenylphenol (97-54-1) + 2-methoxy-phenol (90-05-1)

Guidance literature:

With 10% nickel/activated carbon; hydrogen; In 1,4-dioxane; at 150 ℃; for 2h; under 15001.5 Torr; Autoclave;

DOI:10.1002/cssc.201601273

Reference yield:

lignin (9005-53-2) → 1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + 2-methoxy-4-n-propylphenol (2785-87-7) + 2-methoxy-4-propenylphenol (97-54-1) + 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone (2478-38-8) + 3-methoxy-4-hydroxystyrene (7786-61-0,31853-85-7) + trans-coniferyl aldehyde (458-36-6) + 3-Guaiacylpropanol (2305-13-7) + 1-(4-hydroxy-3-methoxyphenyl)2-propanone (2503-46-0) + Homovanillic acid (306-08-1) + 4-ethylsyringol (14059-92-8) + 1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one (2983-65-5) + 1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (5650-43-1) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2)

Guidance literature:

With water; HUSY (Si/Al=15); at 250 ℃; for 2h; under 5250.53 Torr; Product distribution / selectivity; Inert atmosphere;

Reference yield:

lignin acetosolv type → 4-n-Propylphenol (645-56-7) + 2-Methoxy-4-methylphenol (93-51-6) + 2-methoxy-4-n-propylphenol (2785-87-7) + 2-methoxy-4-propenylphenol (97-54-1) + 4-Ethylguaiacol (2785-89-9) + homovanillyl alcohol (2380-78-1) + 4-propylbenzene-1,2-diol (2525-02-2) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 2-methoxy-phenol (90-05-1) + 4-methyl-1,2-dihydroxybenzene (452-86-8)

Guidance literature:

With 5% palladium on Al₂O₃; hydrogen; In water; at 25 - 310 ℃; for 1h; under 37503.8 Torr; Autoclave;

upstream raw materials:

4-allylguaiacol

α-methyl-(E)-ferulic acid

pinoresinol

ethylmagnesium iodide

Downstream raw materials:

ethyl isoeugenol

2-methoxy-4-propylcyclohexane-1-ol

Vanillin-4-nitrophenylhydrazon

2-methoxy-4-n-propylphenol

Refernces

• 1、 Ahn, Jongmin,Avonto, Cristina,Chittiboyina, Amar G.,Khan, Ikhlas A.. "Is Isoeugenol a Prehapten? Characterization of a Thiol-Reactive Oxidative Byproduct of Isoeugenol and Potential Implications for Skin Sensitization". . p. 948 - 954. Retrieved 2020.
• 2、 Al-Naji, Majd,Antonietti, Markus,Brandi, Francesco. "Controlled lignosulfonate depolymerization: Via solvothermal fragmentation coupled with catalytic hydrogenolysis/hydrogenation in a continuous flow reactor". supporting information. p. 9894 - 9905. Retrieved 2021/12/24.
• 3、 -. "Method for synthesizing vanillin from eugenol through ozone oxidation". Paragraph 0053-0056; 0066-0069; 0078-0081. . Retrieved 2020/12/31.