520-65-0 Usage
Description
ROSMARININE is a pyrrolizidine alkaloid that can be isolated from Senecio rosmarinifolium Linn. This base crystallizes as glistening laminae from either ethanol (EtOH) or acetone (Me2CO). It exhibits optical rotation values of [α]24D 91.5° (MeOH) or -94° (EtOH) and forms a crystalline nitrate with a melting point of 218°C (decomposition). Additionally, it yields a methiodide with a melting point of 251°C. Upon alkaline hydrolysis, ROSMARININE produces rosmarinecine (C23H35O3N) with a melting point of 171-2°C and an optical rotation of [α]25D 118.5° (MeOH), as well as senecic acid (C10H16O5S) with a melting point of 151°C and an optical rotation of [α]25D + 11.8° (EtOH).
Uses
Since the provided materials do not explicitly mention the uses of ROSMARININE, we can only infer potential applications based on its properties and the context of similar compounds. However, it is important to note that the actual uses may vary and require further research and validation.
Used in Pharmaceutical Industry:
ROSMARININE, being an alkaloid, could potentially be used as a starting material for the synthesis of various pharmaceutical compounds. Its unique structural features and optical rotation properties might make it a valuable component in the development of new drugs.
Used in Chemical Research:
Due to its distinct chemical properties and the ability to undergo alkaline hydrolysis, ROSMARININE may be utilized in chemical research to study the reactions and mechanisms involving pyrrolizidine alkaloids. This could contribute to a better understanding of their biological activities and potential applications.
Used in Analytical Chemistry:
The optical rotation values and melting points of ROSMARININE and its derivatives could be useful in analytical chemistry for the identification and characterization of similar compounds. This information might be valuable for quality control and purity assessment in the synthesis of related alkaloids.
References
Richardson, Warren., J. Chem. Soc., 452 (1943)
Kropman, Warren., ibid, 700 (1950)
Check Digit Verification of cas no
The CAS Registry Mumber 520-65-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 0 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 520-65:
(5*5)+(4*2)+(3*0)+(2*6)+(1*5)=50
50 % 10 = 0
So 520-65-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H27NO6/c1-4-11-7-10(2)18(3,23)17(22)24-9-12-13(20)8-19-6-5-14(15(12)19)25-16(11)21/h4,10,12-15,20,23H,5-9H2,1-3H3/t10-,12+,13-,14-,15-,18+/m1/s1
520-65-0Relevant articles and documents
Pyrrolizidine Alkaloid Biosynthesis. Synthesis of 3H-Labelled Trachelanthamidine and Isoretronecanol and their Incorporation into Three Pyrrolizidine Bases (Necines)
Kunec, Ellen K.,Robins, David J.
, p. 1437 - 1441 (2007/10/02)
(+/-)-Isoretronecanol (22) and (+/-)-trachelanthamidine (24) were prepared by 1,3-dipolar cycloaddition of N-formylproline with ethyl propiolate followed by reduction steps.These 3H-labelled 1-hydroxymethylpyrrolizidines together with putrescine were fed to Senecio isatideus which produces retrorsine (1); S. pleistocephalus which yields rosmarinine (8); and Cynoglossum officinale which affords echinatine (5).The double labelling experiments demonstrated that isoretronecanol is incorporated much more efficiently into rosmarinine than into retrorsine or echinatine, whereas trachelanthamidine is a much more efficient precursor for retrorsine and echinatine.Base hydrolysis of retrorsine and echinatine labelled with trachelanthamidine and of rosmarinine labelled with isoretronecanol established that most of the 3H-label was in the base portions, retronecine (2), heliotridine (6), and rosmarinecine (9), respectively.Further degradation of retronecine and rosmarinecine showed that most of the radioactivity was confined to the β-alanine (4) portion.The biosynthetic pathways to isoretronecanol and trachelanthamidine apparently diverge prior to the formation of these 1-hydroxymethylpyrrolizidines, probably during the cyclisation of an immonium ion (14) to form the 1-formylpyrrolizidines (15) and (17).