Supinine

Catalog Number	ACM551586-1
CAS Number	551-58-6
Synonyms	(2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl
IUPAC Name	[(8S)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
Molecular Weight	283.36
Molecular Formula	C15H25NO4
InChI	InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13+,15+/m1/s1
InChI Key	DRVWTOSBCBKXOR-ZLDLUXBVSA-N
Melting Point	148.5 °C
Purity	95%+
Complexity	407
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	3
Exact Mass	283.17835828
Heavy Atom Count	20
Hydrogen Bond Acceptor Count	5
Hydrogen Bond Donor Count	2
Isomeric SMILES	C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O
Monoisotopic Mass	283.17835828
PhysicalState	Powder
Rotatable Bond Count	6
Topological Polar Surface Area	70 Ų

Case Study

Analysis of Diastereomeric Pairs of Pyrrolizidine Alkaloids Including Amabiline/Supinine

Letsyo, Emmanuel, et al. Microchemical Journal, 2020, 157, 104952.

Pyrrolizidine alkaloids (PAs) are toxic to livestock and human health. A large number of PA diastereoisomer pairs were found to exist in L. squarrosa, including intermedine (1) and lycopsamine (2), as well as supinine (3) and amabiline (4). This work first separated these epimeric PA pairs by high-performance countercurrent chromatography (HPCCC), followed by off-line electrospray ionization mass-spectrometry (ESI-MS) and identification of the PAs.
NMR Structure elucidation of PA epimeric pairs (supinine/amabiline)
· The mixture, consisting of the epimeric pair supinine (3) and amabiline (4) with [M+H]+ at m/z 284, was confirmed using 1D/2D-NMR experiments and GC-MS analysis.
· The 1H- and 13C-NMR spectra of the mixture supinine/amabiline displayed similar overlapping signals to epimers intermedine and lycopsamine. Analysis of the HMBC, 1H/1H-COSY, and 1H/1H-NOESY spectra indicated that the necine base was not substituted at C-7 with a hydroxy-function.
· The mixture of supinine (3) and amabiline (4) showed a 62% to 38% ratio of (+)-trachelanthic (2'S,3'R) to (-)-viridifloric (2'S,3'S) necic acid based on the integration of the 13C-signals at position C-2' (d 84.47 and 84.72 ppm) determined by GC-MS analysis.

Custom Q&A

What is the chemical name of Supinine?

SUPININE

What are some synonyms for Supinine?

Spinin, [(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl ester, AI3 51772

What is the CAS number for Supinine?

551-58-6

What is the molecular formula of Supinine?

C15H25NO4

What is the melting point of Supinine?

148.5°C

Where is Supinine obtained from?

Heliotropiurn supinurn

What compound does Supinine furnish on alkaline hydrolysis?

Trachelantic acid and supinidine

How is Supinine excreted from the body?

Through urine as a metabolic pyrrole

What is the boiling point of Supinine (rough estimate)?

425.91°C

What is the refractive index of Supinine (estimate)?

1.5000

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