29588-83-8

Basic information

• Product Name: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-methyl-1,3-dioxo-, (aR)-
• Synonyms: 2-Isoindolineaceticacid, a-methyl-1,3-dioxo-, D- (8CI); 2H-Isoindole-2-acetic acid, 1,3-dihydro-a-methyl-1,3-dioxo-, (R)-; (R)-2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propanoic acid; (R)-2-Phthalimidopropionic acid; N-Phthaloyl-D-alanine; N-Phthalyl-D-alanine; NSC 236670; Phthaloyl-D-alanine
• CAS NO: 29588-83-8
• Molecular Formula: C₁₁H₉NO₄
• Molecular Weight: 219.1935
• Mol File: 29588-83-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 407.9°Cat760mmHg
• Flash Point: 200.5°C
• Density: 1.467g/cm³
• CAS DataBase Reference: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-methyl-1,3-dioxo-, (aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-methyl-1,3-dioxo-, (aR)-(29588-83-8)
• EPA Substance Registry System: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-methyl-1,3-dioxo-, (aR)-(29588-83-8)

Safety Data

• Hazardous Substances Data: 29588-83-8(Hazardous Substances Data)

Upstream product

• 1242459-33-1 C₁₇H₂₅NO₄Si₂ 
• 85-44-9 phthalic anhydride 
• 56-41-7 L-alanine 
• 73365-03-4 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal 
• 338-69-2 D-Alanine 

Downstream Products

• 111114-02-4 (R)-Mesityl-(1-phthalimidoethyl)-keton 
• 2743-80-8 (R)-(3,4-Dimethoxyphenyl)-(1-phthalimidoethyl)-keton 
• 111320-48-0 2,5-Diethoxyphenyl-(1-phthalimidoethyl)-keton 
• 82353-61-5 (R)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 
• 82353-61-5 (2R,3S,4S)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 
• 141725-08-8 (R)-2-Phthalimido-N-(2,6-dimethylphenyl)-N-[3-(3-pyridyl)propyl]propanamide hydrochloride 
• 70386-38-8 L-1-bromo-3-phthalimido-2-butanone 
• 87-41-2 2-benzofuran-1(3H)-one 
• 866395-51-9 2-hydroxymethyl-N-(3-hydroxy-1-methyl-propyl)-benzamide 
• 634585-85-6 ethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-4-methyl-5-oxo-2,5-dihydroisoxazole-3-carboxylate 
• 73365-03-4 (R)-(+)-2-N-phthalimidopropanal 
• 338-69-2 D-Alanine 

Relevant articles and documents

Solid phase-solid state synthesis of N-alkyl imides from anhydrides

Preparation of N-alkyl imides from anhydrides is developed on polymer support in solid state assisted by microwave for the first time.

KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation

A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.

Design, synthesis and mechanism of novel shikonin derivatives as potent anticancer agents

In this study, a series of novel shikonin derivatives (30-49) were designed and synthesized and their anti-proliferative activities were evaluated against five different cancer cell lines, including HeLa, HepG2, MCF-7, BGC and A549. Some of the compounds show strong anti-proliferative effects against HeLa, HepG2 and MCF-7 with IC50 values ranging from 1.26 to 18.50 μM and show lower side effects towards normal cell lines as compared to shikonin. Compared to other compounds and shikonin itself, compound 40 displayed much stronger anti-proliferative effects against various cancer cell lines. Furthermore, the flow cytometry results demonstrated that compound 40 could obviously induce apoptosis in a dose- and time-dependent manner and also cause cell cycle arrest at the G2/M phase. For further investigation of the aforementioned mechanisms, we performed Western blot experiments and found that the cleavage of PARP and upstream caspase-3 increased; moreover, caspase-9 was activated by cleavage but not caspase-8. These aforementioned results also indicate that compound 40 could induce caspase-9 involved apoptosis and G2/M phase cell cycle arrest via the P21, p-CDC2 (Tyr15) pathway independent of P53.