15503-87-4 Usage
Description
NISTC15503874, a pyrrolizidine alkaloid, was first isolated from Crotalaria usaramoensis E. G. Baker and has more recently been found in C. brevifolia and C. rnucronata. This alkaloid exhibits optical rotation with [α]20D + 6.1° (c 0.38, EtOH) or + 7.1° (c 1.83, EtOH) and forms various derivatives such as picrate, picrolonate, reineckate, and methiodide. Upon alkaline hydrolysis, it yields retronecine and retronecic acid, with a melting point of 177-9°C. There is a possibility that NISTC15503874 may be identical with Mucronatine.
Uses
NISTC15503874 has not been explicitly mentioned for any specific application in the provided materials. However, given its classification as a pyrrolizidine alkaloid and its occurrence in various plant species, it may have potential uses in the fields of pharmacology, toxicology, and plant chemistry for further research and understanding of its properties and potential applications.
Hazard
A poison.
References
Culvenor, Smith., Austral. J. Chern., 19,2127 (1966)
Sawhney et al., Ind. J. Chern., 5, 655 (1967)
Check Digit Verification of cas no
The CAS Registry Mumber 15503-87-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,5,0 and 3 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 15503-87:
(7*1)+(6*5)+(5*5)+(4*0)+(3*3)+(2*8)+(1*7)=94
94 % 10 = 4
So 15503-87-4 is a valid CAS Registry Number.
15503-87-4Relevant articles and documents
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Mattocks,A.R.
, p. 225 - 226 (1968)
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Stereoselective Synthesis of the Pyrrolizidine Alkaloids (-)-Integerrimine and (+)-Usaramine
White, James D.,Amedio, John C.,Gut, Samuel,Ohira, Susumu,Jayasinghe, Lalith R.
, p. 2270 - 2284 (2007/10/02)
Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described.The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30.The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol.A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-β-citronellol (36).This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid.A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2).This acid was coupled to the retronecine borane 82 and then lactonized to 2.