1195-94-4

Basic information

• Product Name: (2S)-1,1-dimethyl-2,3,4,5-tetrahydropyrrole-2-carboxylate
• Synonyms: (2S)-1,1-dimethyl-2,3,4,5-tetrahydropyrrole-2-carboxylate;Proline Betaine;homostachydrine
• CAS NO: 1195-94-4
• Molecular Formula: C7H13NO2
• Molecular Weight: 0
• EINECS: 207-445-1
• Mol File: 1195-94-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 207-208 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: (2S)-1,1-dimethyl-2,3,4,5-tetrahydropyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1,1-dimethyl-2,3,4,5-tetrahydropyrrole-2-carboxylate(1195-94-4)
• EPA Substance Registry System: (2S)-1,1-dimethyl-2,3,4,5-tetrahydropyrrole-2-carboxylate(1195-94-4)

Safety Data

• Hazardous Substances Data: 1195-94-4(Hazardous Substances Data)

Usage

Definition

ChEBI: An ammonium betaine that is pipecolic acid zwitterion with methyl groups substituted for the two hydrogens at the nitrogen. It is found in in fruits, seeds, and leaves of orange, lemon, and bergamot.

InChI:InChI=1/C5H9NO2.C5H11NO2/c7-5(8)4-2-1-3-6-4;1-6(2,3)4-5(7)8/h4,6H,1-3H2,(H,7,8);4H2,1-3H3

Upstream product

• 3105-95-1 pipecolinic acid 
• 74-88-4 methyl iodide 
• 4043-87-2 pipecolic Acid 
• 30727-18-5 ethyl 1-methylpiperidine-2-carboxylate 
• 83836-25-3 N,N-Dimethyl-piperidinium-2-carbonsaeure-ethylester-jodid 

Relevant articles and documents

Reactions with Betaine, XIV. Synthesis of Trifluoroacetylmethylide Trifluoroacetates from Betaines

The reaction of trimethylammonium acetic acid betaine (1) with trifluoroaceticanhydride (TFA) yielding trifluoroacetyl-N-methylide can be extended to triethylammonium acetic acid betaine (2), 2-pyridiniumpropionic acid betaine (9) and N,N-dimethyl-piperidinium-2-carboxylate betaine (14).Trigonelline and 3-pyridiniumpropionic acid betaine (11), however, do not react in this way.It follows that the formation of such ylides is only possible if the methylene or methine group of the betaines are flanked by ammonium and carboxylate group. - Keywords: Trifluoroaceticanhydride; Triethylammonio trifluoroacetyl methylide trifluoroacetate; 1-Pyridinio-1-trifluoroacetyl ethylide trifluoroacetate; N,N-Dimethylpiperidinio-2-trifluoroacetyl-2-ylide trifluoroacetate

Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants

The presence of pipecolic acid and pipecolic acid betaine, also known as homostachydrine, is herein reported for the first time in Citrus genus plants. Homostachydrine was found in fruits, seeds, and leaves of orange, lemon, and bergamot (Citrus bergamia Risso et Poit). As homostachydrine was not commercially available, as a comparative source, extracts of alfalfa leaves (Medicago sativa L.) were used, in which homostachydrine is present at high concentration. Then, the results where confirmed by comparison with an authentic standard synthesized and purified starting from pipecolic acid. The synthesized standard was characterized by a ESI-MS/MS study using a 3D ion-trap mass spectrometer. When subjected to MS/MS fragmentation in positive ion mode, homostachydrine, unlike its lower homologue proline betaine (also known as stachydrine), showed a pattern of numerous ionic fragments that allowed unambiguous identification of the compound. For the quantitation in the plant sources, high sensitivity and specificity were achieved by monitoring the transition (158→72), which is absent in the fragmentation patterns of other major osmolytes commonly used as markers for studies of abiotic stress. As for the metabolic origin of homostachydrine, the occurrence in citrus plants of pipecolic acid leads to the hypothesis that it could act as a homostachydrine precursor through direct methylation.

On the investigation of basic constituents of Achillea species.

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