520-62-7

Basic information

• Product Name: (1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol
• Synonyms: (1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol;(5β)-6α-Hydroxy-1-azabicyclo[3.3.0]octane-4α-methanol;(7aα)-Hexahydro-7β-hydroxy-1H-pyrrolizine-1β-methanol;1H-Pyrrolizine-1-methanol, hexahydro-7-hydroxy-, [1S-(1.alpha.,7.alpha.,7A.beta.)]-;Mikanecin;Mikanecine;Nsc124683;Platynecin
• CAS NO: 520-62-7
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.2102
• Mol File: 520-62-7.mol

Chemical Properties

• Boiling Point: 261.9°C at 760 mmHg
• Flash Point: 131.3°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: (1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol(520-62-7)
• EPA Substance Registry System: (1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol(520-62-7)

Safety Data

• Hazardous Substances Data: 520-62-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Drug Discovery:
(1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol is used as a potential candidate in pharmaceuticals and drug discovery due to its unique molecular structure and the biological activities associated with pyrrolizidine compounds.
Used in Chemical Research and Development:
(1R,7S,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol is also utilized in chemical research and development for further investigation of its properties and potential applications, given its stereochemical definition and the presence of functional groups that may offer novel reactivity or interactions in chemical processes.

InChI:InChI=1/C8H15NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h6-8,10-11H,1-5H2/t6-,7-,8-/m1/s1

Upstream product

• 480-85-3 retronecine 
• 41646-10-0 2,3,5,6-Tetrahydro-1H-pyrrolizin-7-carbonsaeure-ethylester 
• 85365-57-7 ethyl (+/-)-1-hydroxy-2,3,5,6-tetrahydro-1H-pyrrolizine-7-carboxylate 

Downstream Products

• 58632-66-9 7,9-di-O-acetylplatynecine 
• 57123-96-3 (7aR)-1t-benzoyloxy-7t-benzoyloximethyl-(7ar)-hexahydro-pyrrolizin 
• 57123-97-4 (7aR)-7t-benzoyloximethyl-(7ar)-hexahydro-pyrrolizin-1t-ol 

Relevant articles and documents

Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases

The endemic Mexican genus Pittocaulon (subtribe Tussilagininae, tribe Senecioneae, Asteraceae) belongs to a monophyletic group of genera distributed in Mexico and North America. The five Pittocaulon species represent shrubs with broom-like succulent branches. All species were found to contain pyrrolizidine alkaloids (PAs). With one exception (i.e., stems of Pittocaulon velatum are devoid of PAs) PAs were found in all plant organs with the highest levels (up to 0.3% of dry weight) in the flower heads. Three structural types of PAs were found: (1) macrocyclic otonecine esters, e.g. senkirkine and acetylpetasitenine; (2) macrocyclic retronecine esters, e.g. senecionine, only found in roots, and (3) monoesters of 1,2-saturated necines with angelic acid. For an unambiguous assignment of the different stereoisomeric 1,2-saturated necine bases a GC-MS method was established that allows the separation and identification of the four stereoisomers as their diacetyl or trimethylsilyl derivatives. All otonecine esters that generally do not form N-oxides and the 1,2-saturated PAs were exclusively found as free bases, while the 1,2-unsaturated 7-angeloylheliotridine occurring in P. velatum was found only as its N-oxide. In a comparative study the 1H and 13C NMR spectra of the four stereoisomeric necine bases were completely assigned by the use of DEPT-135, H,H-COSY, H,C-HSQC and H,H-NOESY experiments and by iterative analysis of the 1H NMR spectra. Based on these methods the PA monoesters occurring in Pittocaulon praecox and P. velatum were assigned as 7-O-angeloyl ester respectively 9-O-angeloyl ester of dihydroxyheliotridane which could be identified for the first time as naturally occurring necine base. Unexpectedly, in the monoesters isolated from the three other Pittocaulon species dihydroxyheliotridane is replaced by the necine base turneforcidine with opposite configuration at C-1 and C-7. The species-specific and organ-typical PA profiles of the five Pittocaulon species are discussed in a biogenetic context.

An Efficient Synthesis of Racemic Necine Bases from a Common Intermediate

Necine bases of pyrrolizidine alkaloids, turneforcidine, hastanecine, and platynecine are synthesized from ethyl 1-hydroxy-2,3,5,6-tetrahydro-1H-pyrrolizine-7-carboxylate in racemic form.