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Sigma-Aldrich

(2S-cis)-(−)-5-Benzyl-3,6-dioxo-2-piperazineacetic acid

97%

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Synonym(s):
(2S,5S)-3,6-Dioxo-5-(phenylmethyl)-2-piperazineacetic acid, Cycloaspartylphenylalanine
Empirical Formula (Hill Notation):
C13H14N2O4
CAS Number:
Molecular Weight:
262.26
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

optical activity

[α]20/D −9.0°, c = 0.9 in acetic acid

mp

270-272 °C (lit.)

SMILES string

OC(=O)C[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC1=O

InChI

1S/C13H14N2O4/c16-11(17)7-10-13(19)14-9(12(18)15-10)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H,14,19)(H,15,18)(H,16,17)/t9-,10-/m0/s1

InChI key

VNHJXYUDIBQDDX-UWVGGRQHSA-N

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This Item
PHR242089274A1321000
Aspartame Related Compound A Pharmaceutical Secondary Standard; Certified Reference Material

PHR2420

Aspartame Related Compound A

Aspartame impurity A European Pharmacopoeia (EP) Reference Standard

A1321000

Aspartame impurity A

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

-

form

powder

form

solid

form

-

form

-

mp

270-272 °C (lit.)

mp

270-272 °C (lit.)

mp

270-272 °C (lit.)

mp

270-272 °C (lit.)

optical activity

[α]20/D −9.0°, c = 0.9 in acetic acid

optical activity

-

optical activity

[α]/D -9.0±1.5°, c = 0.8 in acetic acid

optical activity

-

General description

(2S-cis)-(-)-5-Benzyl-3,6-dioxo-2-piperazineacetic acid is a piperazine scaffold that can be used to construct biologically active compounds with therapeutic applications.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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S Kaakkola et al.
Brain research bulletin, 32(6), 667-672 (1993-01-01)
The effects of two diketopiperazines, Cyclo (His-Pro) (CHP) and Cyclo (Asp-Phe) (CAP), on striatal extracellular levels of dopamine (DA), dihydroxyphenylacetic acid (DOPAC), homovanillic acid (HVA), and 5-hydroxyindoleacetic acid (5-HIAA) were examined using in vivo microdialysis in anaesthetized rats. Treatment with

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