61691-82-5

Basic information

• Product Name: 1'-acetoxyestragole
• Synonyms: 1'-acetoxyestragole;Acetic acid α-vinyl-4-methoxybenzyl ester;p-Methoxy-α-vinylbenzyl alcohol acetate
• CAS NO: 61691-82-5
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• Mol File: 61691-82-5.mol

Chemical Properties

• Boiling Point: 285.09°C (rough estimate)
• Flash Point: 117.1°C
• Appearance: /
• Density: 1.1492 (rough estimate)
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• CAS DataBase Reference: 1'-acetoxyestragole(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-acetoxyestragole(61691-82-5)
• EPA Substance Registry System: 1'-acetoxyestragole(61691-82-5)

Safety Data

• Hazardous Substances Data: 61691-82-5(Hazardous Substances Data)

Usage

Safety Profile

Questionable carcinogen withexperimental carcinogenic data. Human mutation datareported. When heated to decomposition it emits acridsmoke and fumes.

InChI:InChI=1/C12H14O3/c1-4-12(15-9(2)13)10-5-7-11(14-3)8-6-10/h4-8,12H,1H2,2-3H3

Upstream product

• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 108-24-7 acetic anhydride 
• 81701-30-6 (E)-4-methoxycinnamyl acetate 
• 1826-67-1 vinyl magnesium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-36-5 acetyl chloride 
• 53484-50-7 (E)-p-methoxy-cinnamyl alcohol 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 106175-43-3 1,4-bis(4'-methoxyphenyl)hexa-1,5-diene 
• 88044-26-2 (E)-N-benzyl-3-(4-methoxyphenyl)-2-propen-1-amine 
• 81701-30-6 (E)-4-methoxycinnamyl acetate 
• 1282040-44-1 ES-3'-N₂-dG 
• 1282040-43-0 ES-3'-C₈-dG 
• 105401-84-1 (4E)-5-(4-methoxyphenyl)pent-4-en-1-ol 

Relevant articles and documents

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

A Re2O7catalyzed cycloetherification of monoallylic diols

A Re2O7catalyzed cycloetherification of monoallylic diols is described. The reaction features short reaction time, mild reaction conditions and exclusive E selectivity. A wide range of monoallylic alcohols with alkyl or aryl substituents on olefin smoothly undergo ring closure to deliver corresponding oxa-heterocycles. The reaction is also operationally simple and not sensitive to air and moisture.

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1’S-1’-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Nine analogs of 1′S-1′-acetoxychavicol acetate (ACA) were hemi-synthesized and evaluated for their anticancer activities against seven human cancer cell lines. The aim of this study was to investigate the anti-proliferative, apoptotic, and anti-migration effects of these compounds and to explore the plausible underlying mechanisms of action. We found that ACA and all nine analogs were non toxic to human mammary epithelial cells (HMECs) used as normal control cells, and only ACA, 1′-acetoxyeugenol acetate (AEA), and 1′-acetoxy-3,5-dimethoxychavicol acetate (AMCA) inhibited the growth of MDA-MB-231 breast cancer cells with a half-maximal inhibitory concentration (IC50) value of 30.0 μM based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay results, and were selected for further investigation. DNA fragmentation assays showed that these three compounds markedly induced apoptosis of MDA-MB-231 cells. Western blot analysis revealed increased expression levels of cleaved PARP, p53, and Bax, while decreased expression levels of Bcl-2 and Bcl-xL were seen after treatment, indicating that apoptosis was induced via the mitochondrial pathway. Moreover, ACA, AEA, and AMCA effectively inhibited the migration of MDA-MB-231 cells. They also downregulated the expression levels of pFAK/FAK and pAkt/Akt via the integrin β1-mediated signaling pathway. Collectively, ACA and its hemi-synthetic analogs, AEA and AMCA are seen as potential anticancer agents following their abilities to suppress growth, induce apoptosis, and inhibit migration of breast cancer cells.

Kinetic Resolution of Racemic and Branched Monosubstituted Allylic Acetates by a Ruthenium-Catalyzed Regioselective Allylic Etherification

We demonstrated the kinetic resolution of racemic and branched monosubstituted allylic acetates by a ruthenium-catalyzed regioselective allylic etherification. The reaction was effectively catalyzed by the chiral ruthenium catalyst, which was generated by [RuCl2(p-cymene)]2 and (S,S)-iPr-pybox and a catalytic amount of TFA, and both the allylic etherification product and recovered allylic acetate were obtained as an enantiomerically enriched form with up to a 103 s value.

Direct catalytic anti-markovnikov hydroetherification of alkenols

A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenylmalononitrile as a redox-cycling source of a

Highly efficient kinetic resolution of allylic alcohols with terminal double bond

In this study, the lipase-catalyzed kinetic resolution (Novozyme 435) was employed to prepare chiral allylic alcohols and acetates with terminal double bonds in enantiomeric excesses ranging from 94 to >99 %.

Kinetic resolution of allylic alcohols via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic allylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 968. Substituent effect is briefly discussed.

Detection and quantification of specific DNA adducts by liquid chromatography-tandem mass spectrometry in the livers of rats given estragole at the carcinogenic dose

Estragole (ES) is a natural constituent of several herbs and spices that acts as a carcinogen in the livers of rodents. Given that the proximal electrophilic form of ES with a reactive carbocation is generated by cytochrome P450 and a sulfotransferase met

Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes

Silica gel was found to efficiently promote the rearrangement of allylic acetates into their most stable regioisomers under microwave irradiation. The reaction is easy to perform and eco-friendly. This method was applied to the metal-free synthesis of 1,3-enynes.

cis-selective single-cleavage skeletal rearrangement of 1,6-enynes reveals the multifaceted character of the intermediates in metal-catalyzed cycloisomerizations

A skeleton in the closet: The unprecedented title rearrangement of 1,6-enynes has been observed with gold and platinum catalysts (see scheme, [M] = metal catalyst, Z = C(CO2Me)2, R = electron-donating group). This reaction is propose