56271-99-9

Basic information

• Product Name: H-DL-GLA-OH
• Synonyms: DL-GAMMA-CARBOXYGLUTAMIC ACID;DL-GAMMA-CARBOXYGLUTAMIC ACID, MONOAMMONIUM SALT;GAMMA-CARBOXY-DL-GLUTAMIC ACID;GLA;H-DL-GLA-OH;H-DL-GLU(GAMMA-COOH)-OH;H-G-CARBOXY-DL-GLU-OH;H-G-CARBOXY-DL-GLUTAMIC ACID
• CAS NO: 56271-99-9
• Molecular Formula: C₆H₉NO₆
• Molecular Weight: 191.14
• EINECS: 260-087-8
• Mol File: 56271-99-9.mol

Chemical Properties

• Boiling Point: 418 °C at 760 mmHg
• Flash Point: 206.6 °C
• Appearance: Crystalline
• Density: 1.649 g/cm³
• Vapor Pressure: 3.71E-08mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• PKA: 2.13±0.10(Predicted)
• BRN: 2214048
• CAS DataBase Reference: H-DL-GLA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-DL-GLA-OH(56271-99-9)
• EPA Substance Registry System: H-DL-GLA-OH(56271-99-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 56271-99-9(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

InChI:InChI=1/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)

Upstream product

• 56877-43-1 Z-DL-Gla(OtBu)2-OH 
• 56877-40-8 Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 
• 120824-81-9 diethyl benzyloxycarbonyl-γ-carboxy-DL-pyroglutamate 
• 176237-26-6 ethyl (+/-)-2,2-dimethyl-α-nitro-4,6-dioxo-1,3-dioxane-5-propanoate 
• 97458-26-9 N-benzyloxycarbonyl-γ-carboxy-DL-glutamic acid 
• 56877-44-2 γ,γ'-Di-tert-butyl-DL-γ-carboxyglutamic acid 
• 60064-83-7 2-Benzyloxycarbonyl-4-benzyloxycarbonylamino-pentanedioic acid dibenzyl ester 

Downstream Products

• 87770-01-2 4,4-dicarboxy-5-(p-nitrophenyl)proline 
• 117869-42-8 4-carboxy-4-D-5-phenylproline 
• 617-65-2 Glutamic acid 
• 87770-02-3 4,4-dicarboxy-5-(p-methoxyphenyl)proline 
• 87770-00-1 4,4-dicarboxy-5-phenylproline 

Relevant articles and documents

Synthesis and utility of a novel methylene Meldrum's acid precursor

The betaine 1-[(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)methyl]pyridinium hydroxide, inner salt (1), a pyridine adduct of methylene Meldrum's acid is a stable source of methylene Meldrum's acid. It is a versatile reagent which enhances the yields of Diels-Alder and Michael reactions when used instead of traditional methods that generate methylene Meldrum's acid in situ. Diels-Alder reactions performed with this reagent provide products in essentially quantitative yields. Michael reactions result in products in excess of 70% yield. This reagent provides a useful synthetic route to γ-carboxyglutamic acid.

ENZYMATIC RESOLUTION OF γ-CARBOXY-DL-GLUTAMIC ACID

Optically active γ-carboxy-L-glutamic acid was prepared by enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazine, catalyzed by papain (E.C.3.4.22.2), and subsequent removal of the protecting groups from the obtained benzyloxycarbonyl-γ-carboxyl-L-glutamic acid α-phenylhydrazide.