25161-91-5 Usage
Description
Loline is an oily alkaloid derived from the species of grass, Lotium cuneatum Nevski. It has a density of D20 1.1343 and a refractive index of n20D 1.5505. Loline behaves as a diacidic base, yielding a series of well-crystalline salts and derivatives. The alkaloid possesses an ether oxygen bridging the pyrrolizidine moiety.
Uses
1. Used in Pharmaceutical Industry:
Loline is used as a diacidic base for its ability to yield a series of well-crystalline salts and derivatives, which can be utilized in the development of various pharmaceutical products.
2. Used in Chemical Research:
Loline is used as a subject of study for its unique properties, such as its diacidic base behavior and the formation of well-crystalline salts and derivatives, contributing to the advancement of chemical knowledge and potential applications in various fields.
3. Used in Agricultural Industry:
Loline, being derived from a species of grass, can be studied for its potential applications in agriculture, such as pest control or as a natural alternative to synthetic chemicals in crop protection.
4. Used in Analytical Chemistry:
Loline's unique properties, including its diacidic base behavior and the formation of well-crystalline salts and derivatives, make it a potential candidate for use in analytical chemistry for the development of new methods or techniques for substance identification and quantification.
Hazard
A poison.
References
Yunusov, Akramov., J. Gen. Chern., USSR, 25, 1765 (1955)
Yunusov, Akramov., ibid, 30,699,705,3105 (1960)
Check Digit Verification of cas no
The CAS Registry Mumber 25161-91-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,1,6 and 1 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 25161-91:
(7*2)+(6*5)+(5*1)+(4*6)+(3*1)+(2*9)+(1*1)=95
95 % 10 = 5
So 25161-91-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H14N2O/c1-9-7-6-4-10-3-2-5(11-6)8(7)10/h5-9H,2-4H2,1H3/t5-,6+,7-,8+/m0/s1
25161-91-5Relevant articles and documents
An efficient synthesis of loline alkaloids
Cakmak, Mesut,Mayer, Peter,Trauner, Dirk
supporting information; experimental part, p. 543 - 545 (2012/04/04)
Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.
Asymmetric synthesis of (+)-loline
Blakemore, Paul R.,Schulze, Volker K.,White, James D.
, p. 1263 - 1264 (2007/10/03)
The first asymmetric synthesis of (+)-loline has been achieved in 20 steps from (-)-malic acid by a route incorporating intramolecular hetero- Diels-Alder cycloaddition of an acylnitrosodiene.
