480-79-5 Usage
Description
INTEGERRIMINE is a pyrrolizidine alkaloid derived from Senecio leucanthemifolius Poiret, a plant species known for its antimicrobial properties. It is also found in several other species of Senecio and Crotalaria. INTEGERRIMINE can be crystallized as a picrate with a melting point of 224°C. Upon alkaline hydrolysis, it forms retronecine and integerrinecic acid (C10H160S), which has a melting point of 132°C and is dibasic.
Uses
Used in Pharmaceutical Industry:
INTEGERRIMINE is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms. Its effectiveness against bacteria, fungi, and other pathogens makes it a valuable compound in the development of new drugs and treatments for infectious diseases.
Used in Agricultural Industry:
INTEGERRIMINE's antimicrobial properties can also be applied in the agricultural industry to protect crops from harmful pathogens and pests. By incorporating INTEGERRIMINE into pesticides or fungicides, farmers can improve crop yield and reduce the spread of diseases in their fields.
Used in Cosmetics Industry:
In the cosmetics industry, INTEGERRIMINE can be used as an active ingredient in products designed to combat microbial growth on the skin. This can be particularly useful in skincare products that aim to reduce acne, fungal infections, or other skin-related issues caused by microbial imbalances.
Used in Research and Development:
INTEGERRIMINE's unique chemical properties and antimicrobial activity make it an interesting compound for further research and development. Scientists can study its structure and interactions with other molecules to potentially discover new applications or develop more effective drugs based on its properties.
References
Manske., Can. 1. Res., 17B, 1,8 (1939)
Adams, van Doulen.,J. Arner. Chern. Soc., 75,4631 (1953)
Gellest, Mate., Austral. 1. Chern., 17, 158 (1964)
Check Digit Verification of cas no
The CAS Registry Mumber 480-79-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 0 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 480-79:
(5*4)+(4*8)+(3*0)+(2*7)+(1*9)=75
75 % 10 = 5
So 480-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3
480-79-5Relevant articles and documents
A synthesis of senecionine, a representative of hepatoxic, macrocyclic pyrrolizidine alkaloids of retronecine type
Niwa,Sakata,Yamada
, p. 1990 - 1993 (2007/10/02)
Described is a synthesis of (-)-senecionine, the best-known hepatoxic, 12-membered pyrrolizidine alkaloid of retronecine type. Integerrinecic acid lactone methyl ester was converted into protected senecic acid, which was regioselectively coupled with (+)-retronecine, achieving the first synthesis of (-)-senecionine.
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.
Total synthesis of optically active integerrimine, a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type. III. Regioselective elaboration of the unsymmetrical twelve-membered dilactone and total synthesis of (-)-integerrimine
Niwa,Miyachi,Uosaki,et al.
, p. 4609 - 4610 (2007/10/02)
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