120-11-6

Basic information

• Product Name: 1-Benzyloxy-2-methoxy-4-propenylbenzene
• Synonyms: 1-(Benzyloxy)-2-methoxy-4-[(1E)-1-propenyl]benzene;1-(benzyloxy)-2-methoxy-4-propenyl-benzen;1-.alpha.-Phenyl-4-propenylveratrole;2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzen;2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-Benzene;Benzene, 1-(benzyloxy)-2-methoxy-4-propenyl-;Benzene, 2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-;Benzyl alcohol, ether with isoeugenol
• CAS NO: 120-11-6
• Molecular Formula: C₁₇H₁₈O₂
• Molecular Weight: 254.32
• EINECS: 204-370-6
• Mol File: 120-11-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 59-63 °C(lit.)
• Boiling Point: 357.54°C (rough estimate)
• Flash Point: 152.122 °C
• Appearance: White crystalline power
• Density: 1.0621 (rough estimate)
• Vapor Pressure: 6.76E-06mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-Benzyloxy-2-methoxy-4-propenylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyloxy-2-methoxy-4-propenylbenzene(120-11-6)
• EPA Substance Registry System: 1-Benzyloxy-2-methoxy-4-propenylbenzene(120-11-6)

Safety Data

• WGK Germany: 3
• RTECS: CY8225000
• Hazardous Substances Data: 120-11-6(Hazardous Substances Data)

Usage

Description

Isoeugenyl benzyl ether has a faint, floral odor of rose-carnation. May be synthesized by benzylation of isoeugenol; also by alkaline isomerization of benzyleugenol.

Chemical Properties

Isoeugenyl benzyl ether has a faint, floral odor of rose–carnation

Preparation

By benzylation of isoeugenol; also by alkaline isomerization of benzyleugenol

Safety Profile

Mildly toxic by ingestion. A skinirritant. When heated todecomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C17H18O2/c1-3-7-14-10-11-16(17(12-14)18-2)19-13-15-8-5-4-6-9-15/h3-12H,13H2,1-2H3/b7-3-

Synthetic route

2-methoxy-4-propenylphenol (97-54-1) + benzyl bromide (100-39-0) → 2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene (120-11-6)

Conditions	Yield
Stage #1: 2-methoxy-4-propenylphenol With potassium carbonate In N,N-dimethyl-formamide for 2h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 60℃; for 12h;

2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene (120-11-6) → 1-(benzyloxy)-2-methoxy-4-propylbenzene (13335-50-7)

Conditions	Yield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;	100%
With hydrogen In methanol at 25℃; for 3h;	99%
With hydrogen In methanol at 20℃; for 5h; chemoselective reaction;	98%
With palladium on activated charcoal; hydrogen In 1,4-dioxane at 20℃; for 24h; chemoselective reaction;	98%

2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene (120-11-6) → 2-methoxy-4-n-propylphenol (2785-87-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent);	100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 3.5h; Reagent/catalyst; chemoselective reaction;	100%
With hydrogen In methanol at 20℃; for 18h; chemoselective reaction;	99%

2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene (120-11-6) + Acetyl bromide (506-96-7) → 2-methoxy-4-(prop-1-enyl)phenyl acetate

Conditions	Yield
With lithium bromide In dichloromethane at 30 - 35℃; for 12h; Inert atmosphere; regioselective reaction;	75%

2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene (120-11-6) + flindersine (523-64-8) → (1RS,2RS,2aRS,10aSR)-1,10,10-trimethyl-2-(3-methoxy-4-benzyloxyphenyl)-1,2,2a,4,10,10a-hexahydro-3H-cyclobuta[4,5]pyrano[3,2-c]quinolin-3-one

Conditions	Yield
In neat (no solvent) for 16h; Microwave irradiation;	3%

Upstream product

• 97-54-1 2-methoxy-4-propenylphenol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 93-29-8 2-methoxy-4-(prop-1-enyl)phenyl acetate 
• 2785-87-7 2-methoxy-4-n-propylphenol 
• 13335-50-7 1-(benzyloxy)-2-methoxy-4-propylbenzene 

Relevant articles and documents

Control of ER-positive breast cancer by ERα expression inhibition, apoptosis induction, cell cycle arrest using semisynthetic isoeugenol derivatives

New semi-synthetic effective and safe anticancer agents isoeugenol derivatives were synthesized, characterized, and screened for their cytotoxic activity against MCF-7. Moreover, their selective cytotoxicity was assessed against MCF-10A. Three derivatives, 2, 8 and 10 were significantly more active than the reference drug 5-FU with IC50 values of 6.59, 8.07 and 9.63 and 30.93 μM, respectively. Also interestingly, these derivatives demonstrated some degree of selectivity to cancer cells over normal cells. Furthermore, derivative 2 was subjected to other in vitro experiments against MCF-7 where it inhibited colony formation by 87.5% and lowered ERα concentration to 395.7 pg/mL compared to 1129 pg/mL in untreated control cells. In continuation of the investigation, the apoptotic activity of compound 2, was assessed where it significantly enhanced total apoptotic cell death by 9.16-fold (18.70% compared to 1.64% for the untreated MCF-7 control cells) and arrested the cell cycle at the G2/M phase. Furthermore, the molecular mechanism of apoptotic activity was investigated at both the gene (RT-PCR) and protein (western plotting) levels where upregulation of pro-apoptotic and down regulation of anti-apoptotic genes was detected. Additionally, compound 2 treatment enhanced the antioxidant (GSH, CAT, SOD) activities. Finally, in vivo experiments verified the effective anticancer activity of compound 2 through inhibition of tumor proliferation by 47.6% compared to 22.9% for 5-FU and amelioration of the hematological, biochemical, and histopathological examinations near normal. In effect, compound 2 can be viewed as a promising semi-synthetic derivative of isoeugenol with some degree of selectivity for management of breast cancer through apoptotic induction and ERα downregulation.