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2-Benzylsuccinic acid

CAS# 3972-36-9

2-Benzylsuccinic acid

Catalog No. BCC8566----Order now to get a substantial discount!

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2-Benzylsuccinic acid: 5mg $17 In Stock
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Chemical structure

2-Benzylsuccinic acid

3D structure

Chemical Properties of 2-Benzylsuccinic acid

Cas No. 3972-36-9 SDF Download SDF
PubChem ID 446168 Appearance Powder
Formula C11H12O4 M.Wt 208
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-2-benzylbutanedioic acid
SMILES C1=CC=C(C=C1)CC(CC(=O)O)C(=O)O
Standard InChIKey GTOFKXZQQDSVFH-VIFPVBQESA-N
Standard InChI InChI=1S/C11H12O4/c12-10(13)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)(H,14,15)/t9-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

2-Benzylsuccinic acid Dilution Calculator

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2-Benzylsuccinic acid Molarity Calculator

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Preparing Stock Solutions of 2-Benzylsuccinic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.8077 mL 24.0385 mL 48.0769 mL 96.1538 mL 120.1923 mL
5 mM 0.9615 mL 4.8077 mL 9.6154 mL 19.2308 mL 24.0385 mL
10 mM 0.4808 mL 2.4038 mL 4.8077 mL 9.6154 mL 12.0192 mL
50 mM 0.0962 mL 0.4808 mL 0.9615 mL 1.9231 mL 2.4038 mL
100 mM 0.0481 mL 0.2404 mL 0.4808 mL 0.9615 mL 1.2019 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 2-Benzylsuccinic acid

Benzyl radical addition reaction through the homolytic cleavage of a benzylic C-H bond.[Pubmed:21331427]

Org Biomol Chem. 2011 Apr 7;9(7):2062-4.

Direct generation of a benzyl radical by C-H bond activation of toluenes and the addition reaction of the resulting radical to an electron deficient olefin were developed. The reaction of dimethyl fumarate with toluene in the presence of Et(3)B as a radical initiator at reflux afforded 2-Benzylsuccinic acid dimethyl ester in good yield.

Mechanistic insight into the inactivation of carboxypeptidase A by alpha-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid, a novel type of irreversible inhibitor for carboxypeptidase A with no stereospecificity.[Pubmed:11559199]

J Org Chem. 2001 Sep 21;66(19):6462-71.

On the basis of the active site topology and enzymic catalytic mechanism of carboxypeptidase A (CPA), a prototypical zinc-containing proteolytic enzyme, alpha-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid (1), was designed as a novel type of mechanism-based inactivator of the enzyme. All four possible stereoisomers of the inhibitor were synthesized in an enantiomerically pure form starting with optically active aspartic acid, and their CPA inhibitory activities were evaluated to find that surprisingly all of the four stereoisomers inhibit CPA in a time dependent manner. The inhibited enzyme did not regain its enzymic activity upon dialysis. The inactivations were prevented by 2-Benzylsuccinic acid, a competitive inhibitor that is known to bind the active site of the enzyme. These kinetic results strongly support that the inactivators attach covalently to the enzyme at the active site. The analysis of ESI mass spectral data of the inactivated CPA ascertained the conclusion from the kinetic results. The values of second-order inhibitory rate constants (k(obs)/[I](o)) fall in the range of 1.7-3.6 M(-1) min(-1). The lack of stereospecificity shown in the inactivation led us to propose that the ring cleavage occurs by the nucleophilic attack at the 2-position rather than at the 5-position and the ring opening takes place in an addition-elimination mechanism. The tetrahedral transition state that would be generated in this pathway is thought to be stabilized by the active site zinc ion, which was supported by the PM3 semiemprical calculations. In addition, alpha-benzyl-2-oxo-1,3-oxazolidine-5-acetic acid (18), a structural isomer of 1 was also found to inactivate CPA in an irreversible manner, reinforcing the nucleophilic addition-elimination mechanism. The present study demonstrates that the transition state for the inactivation pathway plays a critical role in determining stereochemistry of the inactivation.

[Preparation of optically active succinic acid derivatives. III. Regioselective condensation reactions of optically active 2-substituted succinic acids with diimidazolide].[Pubmed:9629061]

Yakugaku Zasshi. 1998 Jun;118(6):248-55.

We investigated the large scale synthesis of monocalcium bis [(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl) propionate] dihydrate (KAD-1229), which has a potent hypoglycemic effect, in a single reaction vessel. (2S)-2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl) propionic acid (7) was directly obtainable from (S)-2-Benzylsuccinic acid (2) and cis-hexahydroisoindoline (4), without the isolation of intermediates by the method using thionyldiimidazole (9) and/or diimidazolide of the acid 2. Sequential reaction of imidazole with thionyl chloride, 2, and 4, followed by acid catalyzed hydrolysis gave amidecarboxylic acid 7 in 86% overall yield. The acid 7 was treated with 2 N NaOH, followed by the treatment with calcium chloride to give KAD-1229 in 91% yield.

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