120-11-6 Usage
Description
1-Benzyloxy-2-methoxy-4-propenylbenzene, also known as Isoeugenyl benzyl ether, is an organic compound with a molecular formula of C17H18O2. It is characterized by its faint, floral odor reminiscent of rose-carnation. 1-Benzyloxy-2-methoxy-4-propenylbenzene can be synthesized through the benzylation of isoeugenol or by alkaline isomerization of benzyleugenol. Isoeugenyl benzyl ether is known for its chemical properties, which include its distinct fragrance and potential applications in various industries.
Uses
Used in Fragrance Industry:
1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a fragrance ingredient for its [floral, rose-carnation] scent. The expression is: 1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a fragrance ingredient for [creating a floral, rose-carnation scent] due to its [distinct and faint odor].
Used in Flavor Industry:
1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a flavoring agent for [adding a unique, floral taste] to various food and beverage products. The expression is: 1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a flavoring agent for [enhancing the taste of food and beverages] with its [floral, rose-carnation flavor].
Used in Pharmaceutical Industry:
1-Benzyloxy-2-methoxy-4-propenylbenzene may be used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. The expression is: 1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a starting material or intermediate for [synthesis of pharmaceutical compounds] due to its [chemical reactivity and structural properties].
Used in Chemical Research:
1-Benzyloxy-2-methoxy-4-propenylbenzene serves as a valuable compound for research purposes in the field of organic chemistry. The expression is: 1-Benzyloxy-2-methoxy-4-propenylbenzene is used as a research compound for [exploring its chemical properties and potential applications] in the field of [organic chemistry].
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.
Check Digit Verification of cas no
The CAS Registry Mumber 120-11-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 120-11:
(5*1)+(4*2)+(3*0)+(2*1)+(1*1)=16
16 % 10 = 6
So 120-11-6 is a valid CAS Registry Number.
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-
120-11-6Relevant articles and documents
Control of ER-positive breast cancer by ERα expression inhibition, apoptosis induction, cell cycle arrest using semisynthetic isoeugenol derivatives
Nafie, Mohamed S.,Elghazawy, Nehal H.,Owf, Salma M.,Arafa, Kholoud,Abdel-Rahman, Mohamed A.,Arafa, Reem K.
, (2021/11/26)
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.