6367-42-6

Basic information

• Product Name: H-D-ASP-OBZL
• Synonyms: H-D-ASP-OBZL;D-ASPARTIC ACID-OBZL;D-ASPARTIC ACID ALPHA-BENZYL ESTER;D-aspartic acid A-benzyl ester;(3S)-3-AMMonio-4-(benzyloxy)-4-oxobutanoate;N-(Phenylmethyl)-D-aspartic acid;(R)-2-(BenzylaMino)succinic acid;D-Asp-OBzl
• CAS NO: 6367-42-6
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• Product Categories: Amino Acids Derivatives;Amino Acids and Derivatives;A - H;Amino Acids;Modified Amino Acids
• Mol File: 6367-42-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 209℃
• Boiling Point: 376.738 °C at 760 mmHg
• Flash Point: 181.645 °C
• Appearance: /
• Density: 1.311 g/cm³
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: −20°C
• CAS DataBase Reference: H-D-ASP-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-ASP-OBZL(6367-42-6)
• EPA Substance Registry System: H-D-ASP-OBZL(6367-42-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6367-42-6(Hazardous Substances Data)

Usage

General Description

H-D-ASP-OBZL is a synthetic chemical compound that functions as a potent and selective inhibitor of the enzyme FAAH (fatty acid amide hydrolase). It is commonly used in scientific research to study the endocannabinoid system and the role of FAAH in the regulation of endocannabinoid signaling. By inhibiting FAAH, H-D-ASP-OBZL can increase the levels of endogenous cannabinoids, such as anandamide, leading to potential therapeutic effects for conditions such as pain, inflammation, and anxiety. Its unique structure and high potency make it a valuable tool for investigating the biological functions of the endocannabinoid system and developing new treatments targeting FAAH.

InChI:InChI=1/C11H13NO4/c13-10(14)6-9(11(15)16)12-7-8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H,13,14)(H,15,16)/t9-/m1/s1

Upstream product

• 1783-96-6 (2R)-aspartic acid 
• 100-52-7 benzaldehyde 
• 84028-93-3 (R)-Benzylasparaginsaeure-diethylester 

Relevant articles and documents

Engineered C–N Lyase: Enantioselective Synthesis of Chiral Synthons for Artificial Dipeptide Sweeteners

Aspartic acid derivatives with branched N-alkyl or N-arylalkyl substituents are valuable precursors to artificial dipeptide sweeteners such as neotame and advantame. The development of a biocatalyst to synthesize these compounds in a single asymmetric step is an as yet unmet challenge. Reported here is an enantioselective biocatalytic synthesis of various difficult N-substituted aspartic acids, including N-(3,3-dimethylbutyl)-l-aspartic acid and N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-l-aspartic acid, precursors to neotame and advantame, respectively, using an engineered variant of ethylenediamine-N,N′-disuccinic acid (EDDS) lyase from Chelativorans sp. BNC1. This engineered C–N lyase (mutant D290M/Y320M) displayed a remarkable 1140-fold increase in activity for the selective hydroamination of fumarate compared to that of the wild-type enzyme. These results present new opportunities to develop practical multienzymatic processes for the more sustainable and step-economic synthesis of an important class of food additives.

Amino Acids, 4 - Enantioselective Synthesis of N-Substituted α-Amino Carboxylic Acids from α-Hydroxy Carboxylic Acids

With primary and secondary amines, the (S)-α-(trifluoromethylsulfonyloxy) carboxylates (S)-3 afford in an SN2 reaction the N-substituted (R)-α-amino carboxylates (R)-5, (R)-9, and (R)-12, resp.The rates of α-substituted ethyl propionates decrease in the order of the substituents triflate (3a) >> bromide (8a) > mesylate (7a) >= tosylate (7b) > chloride (8b); in the reactions with amines, decreasing reactivity affords increasing racemisation and elimination as a consequence of the more drastic conditions which are required