CAS 27841-97-0

[(1S,2R,7aR)-Hexahydro-2-hydroxy-1H-pyrrolizin-1-yl]methyl (2Z)-2-methyl-2-butenoate

Description:

The chemical substance known as [(1S,2R,7aR)-Hexahydro-2-hydroxy-1H-pyrrolizin-1-yl]methyl (2Z)-2-methyl-2-butenoate, with the CAS number 27841-97-0, is an organic compound characterized by its complex structure, which includes a pyrrolizine ring and an ester functional group. This compound features a hexahydro-pyrrolizin moiety that contributes to its stereochemistry, indicated by the specific stereocenters at positions 1, 2, and 7a. The presence of the hydroxy group enhances its potential for hydrogen bonding, influencing its solubility and reactivity. The (2Z)-2-methyl-2-butenoate part of the molecule suggests that it may participate in various chemical reactions typical of esters, such as hydrolysis or transesterification. The compound's unique structure may confer specific biological activities, making it of interest in medicinal chemistry and pharmacology. Overall, its characteristics, including molecular geometry, functional groups, and stereochemistry, play a crucial role in determining its chemical behavior and potential applications.

Formula: C₁₃H₂₁NO₃

InChI: InChI=1S/C13H21NO3/c1-3-9(2)13(16)17-8-10-11-5-4-6-14(11)7-12(10)15/h3,10-12,15H,4-8H2,1-2H3/b9-3-/t10-,11-,12+/m1/s1

InChI key: InChIKey=LVZCTOQMFLAKLI-CSZIUDOQSA-N

SMILES: C(OC(/C(=C\C)/C)=O)[C@@H]1[C@@]2(N(C[C@@H]1O)CCC2)[H]

Synonyms:

• 2-Butenoic acid, 2-methyl-, [(1S,2R,7aR)-hexahydro-2-hydroxy-1H-pyrrolizin-1-yl]methyl ester, (2Z)-
• Macrophylline
• Macrophylline (Senecio)
• [(1S,2R,7aR)-Hexahydro-2-hydroxy-1H-pyrrolizin-1-yl]methyl (2Z)-2-methyl-2-butenoate
• 2-Butenoic acid, 2-methyl-, (hexahydro-2-hydroxy-1H-pyrrolizin-1-yl)methyl ester, [1S-[1α(Z),2α,7aα]]-

Macrophylline

CAS: 27841-97-0

Macrophylline A shows weak inhibitory action on KCl-induced contraction.

Formula: C₁₃H₂₁NO₃

Purity: 98%

Color and Shape: Solid

Molecular weight: 239.31

Ref: TM-TN4484

Macrophylline

CAS: 27841-97-0

Macrophylline is a bronchodilator, which is a synthetic pharmaceutical compound. It primarily originates from the class of xanthine derivatives, known for their ability to relax and open air passages in the lungs. The mode of action involves inhibiting phosphodiesterase enzymes leading to increased cyclic AMP levels. This results in bronchodilation and enhanced respiratory efficiency, reducing bronchospasm in the respiratory tract.

Formula: C₁₃H₂₁NO₃

Purity: Min. 95%

Molecular weight: 239.31 g/mol

Ref: 3D-CBA84197