162853-41-0

Basic information

• Product Name: METHYL 7-PHENYLCARBAMOYLHEPTANATE
• Synonyms: METHYL 7-PHENYLCARBAMOYLHEPTANATE;8-Oxo-8-(phenylamino)octanoic acid methyl ester;Methyl 8-oxo-8-(phenylaMino)octanoate;Methyl 7-Phenylcarbamoylheptanoate
• CAS NO: 162853-41-0
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.33
• Mol File: 162853-41-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 64-65℃
• Boiling Point: 425.6±28.0 °C(Predicted)
• Appearance: /
• Density: 1.090
• Storage Temp.: 2-8°C
• PKA: 15.02±0.70(Predicted)
• CAS DataBase Reference: METHYL 7-PHENYLCARBAMOYLHEPTANATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 7-PHENYLCARBAMOYLHEPTANATE(162853-41-0)
• EPA Substance Registry System: METHYL 7-PHENYLCARBAMOYLHEPTANATE(162853-41-0)

Safety Data

• Hazardous Substances Data: 162853-41-0(Hazardous Substances Data)

Usage

General Description

Methyl 7-phenylcarbamoylheptanate is a chemical compound commonly used in the production of perfumes and flavorings. It is a clear, colorless liquid with a sweet, floral odor. METHYL 7-PHENYLCARBAMOYLHEPTANATE is often added to products such as air fresheners, soaps, and cosmetics to enhance their scent. It is also used as a flavoring agent in food and beverages. Additionally, methyl 7-phenylcarbamoylheptanate has been studied for its potential benefits in treating inflammatory and neurodegenerative diseases due to its anti-inflammatory and antioxidant properties. However, its safety and potential side effects in such applications are still being evaluated.

Upstream product

• 67-56-1 methanol 
• 149648-52-2 suberanilic acid 
• 41624-92-4 methyl 8-chloro-8-oxooctanoate 
• 62-53-3 aniline 
• 3946-32-5 suberic acid monomethyl ester 
• 505-48-6 octane-1,8-dioic acid 
• 10521-06-9 oxonane-2,9-dione 
• 5454-83-1 5-bromovaleric acid methyl ester 
• 2210-24-4 N-acryloylaniline 

Downstream Products

• 149647-78-9 vorinostat 
• 149648-52-2 suberanilic acid 
• 852619-59-1 octanedioic acid phenylamide (2-tritylsulfanyl-ethyl)-amide 
• 1017261-04-9 7-(1H-indol-2-yl)-N-phenylheptanamide 
• 1227736-21-1 suberoylanilide hydroxamic acid potassium salt 

Relevant articles and documents

An Endogenous Reactive Oxygen Species (ROS)-Activated Histone Deacetylase Inhibitor Prodrug for Cancer Chemotherapy

Suberoylanilide hydroxamic acid (SAHA, vorinostat) is a potent small-molecule pan-inhibitor of histone deacetylases (HDACs) approved for treatment of cutaneous T-cell lymphoma (CTCL). However, SAHA exhibits poor selectivity for cancer cells over noncancer cells. With an aim to improving its selectivity for cancer cells, we generated a novel SAHA prodrug (SAHA-OBP) that is activated in the presence of hydrogen peroxide, a reactive oxygen species (ROS) known to be overexpressed in cancer cells. The high endogenous ROS content in cancer cells triggers rapid removal of the 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl carbonyl (OBP) cap to release active SAHA. The SAHA-OBP prodrug demonstrates selective activity against multiple cancer cell lines such as HeLa, MCF-7, MDA-MB-231, and B16-F10, while remaining benign toward noncancer cells. The downstream effects of SAHA released from SAHA-OBP in cancer cells is the induction of apoptosis. SAHA-OBP was also found to be effective on multicellular tumor spheroids (MCTS). The SAHA prodrug designed in this study undergoes rapid ROS-dependent activation and imparts much-needed selectivity to SAHA for cancer cells.

H2O2/Peroxynitrite-Activated Hydroxamic Acid HDAC Inhibitor Prodrugs Show Antileukemic Activities against AML Cells

Occurrence of acute myeloid leukemia (AML) results in abundant endogenous reactive oxygen species (ROS)/reactive nitrogen species (RNS) in AML cells and in disease-relevant microenvironments. Histone deacetylase inhibitor (HDACi) prodrug approach was designed accordingly by masking the hydroxamic acid zinc binding group with hydrogen peroxide (H2O2)/peroxynitrite (PNT)-sensitive, self-immolative aryl boronic acid moiety. Model prodrugs 5-82 and 5-23 were activated in AML cells to release cytotoxic HDACis, evidenced by inducing acetylation markers and reducing viability of AML cells. Intracellular activation and antileukemic activities of prodrug were increased or decreased by ROS/PNT inducers and scavengers, respectively. Prodrugs 5-82 and 5-23 also enhanced the potency of chemotherapy drug cytarabine, supporting the potentials of this prodrug class in combinatorial treatment.

Method for preparing anticarcinogen vorinostat

The invention discloses a method for preparing anticarcinogen vorinostat. The method includes: (1) subjecting suberic anhydride and aniline to contact reaction in water and 1,4-dioxane at the temperature of 5-10 DEG C in the presence of CuI, performing filtering after reaction is finished, regulating the pH of filtrate to 5-6, performing suction filtration, washing filter cake obtained after suction filtration, and drying to obtain 7-phenylcarbamoylheptanoic acid; (2) dissolving the 7-phenylcarbamoylheptanoic acid in methanol, adding cation exchange resin and ZnCl2, heating to 50-55 DEG C for reaction for 3 hours, concentrating, extracting with ethyl acetate, concentrating, washing with petroleum ether, and drying to obtain suberanilic acid methyl ester; (3) subjecting hydroxylamine hydrochloride and sodium methoxide to stirring reaction in absolute methanol for 0.5-1h, filtering prior to adding the suberanilic acid methyl ester into filtrate for reaction at the temperature of 40 DEG C for 3-5 hours, cooling to room temperature, regulating the pH to 7, performing suction filtration, washing filter cake, and performing recrystallization with ethyl alcohol to obtain the vorinostat. The method is high in yield, quick in reaction and simple to operate.