15503-87-4

Basic information

• Product Name: NISTC15503874
• Synonyms: NISTC15503874;(15E)-12,18-Dihydroxysenecionan-11,16-dione;Usaramine;Mucronatine;(15E)-Retrorsine;trans-Retrorsine;Usaramin
• CAS NO: 15503-87-4
• Molecular Formula: C18H25NO6
• Molecular Weight: 351.3942
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 15503-87-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 178-180℃
• Boiling Point: 583.2°Cat760mmHg
• Flash Point: 306.5°C
• Appearance: /
• Density: 1.32±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 12.00±0.40(Predicted)
• CAS DataBase Reference: NISTC15503874(CAS DataBase Reference)
• NIST Chemistry Reference: NISTC15503874(15503-87-4)
• EPA Substance Registry System: NISTC15503874(15503-87-4)

Safety Data

• Hazard Codes: A poison.:
• Safety Statements: x." target="_blank">A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.:
• Hazardous Substances Data: 15503-87-4(Hazardous Substances Data)

Usage

Description

A pyrrolizidine alkaloid first isolated from Crotalaria usararnoensis E. G. Baker, this base has more recently been found in C. brevifolia and C. rnucronata. The alkaloid has [α]20D + 6.1° (c 0.38, EtOH) or + 7.1° (c 1.83, EtOH). It yields a picrate, m.p. 230- 2°C (dec.); picrolonate, m.p. 148-150°C (dec.); reineckate, m.p. 190-2°C (dec.) and methiodide, m.p. 229-230°C (dec.). Alkaline hydrolysis furnishes retronecine and retronecic acid, m.p. 177-9°C. It has been suggested that the base may be identical with Mucronatine (q.v.).

Hazard

A poison.

References

Culvenor, Smith., Austral. J. Chern., 19,2127 (1966) Sawhney et al., Ind. J. Chern., 5, 655 (1967)

Upstream product

• 82485-07-2 9-O-(tert-Butyldimethylsilyl)retronecine 
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• 2385-77-5 (R)-Citronellal 
• 1117-61-9 (3R)-citronellol 
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• 120093-49-4 (3R)-α-methylene-3,7-dimethyl-6-octen-1-al 
• 122445-38-9 (4R)-2,2-Dimethyl-4-<1(1R)-1,5-dimethyl-4-hexenyl>-4-(hydroxymethyl)-1,3-dioxolane 
• 122445-36-7 (2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate 
• 139608-86-9 (S)-4-((R)-1,5-Dimethyl-hex-4-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 122445-39-0 (4S)-4-Carbomethoxy-2,2-dimethyl-4-<(1R)-1,5-dimethyl-4-hexenyl>-1,3-dioxolane 
• 122445-42-5 (2S,3R)-2-Hydroxy-2-hydroxymethyl-3-methyl-hexanedioic acid 1-(2-trimethylsilanyl-ethyl) ester 
• 122445-43-6 (4R,5S)-5-<<2-(Trimethylsilyl)ethoxy>carbonyl>-5-(hydroxymethyl)-4-methyl-5-pentanolide 
• 122445-37-8 (4S)-2,2-Dimethyl-4-<1(1R)-1,5-dimethyl-4-hexenyl>-4-<(pivalyloxy)methyl>-1,3-dioxolane 
• 122445-47-0 (2S,3R)-5-Eth-(E)-ylidene-2-hydroxy-2-hydroxymethyl-3-methyl-hexanedioic acid 1-(2-trimethylsilanyl-ethyl) ester 

Downstream Products

• 23092-97-9 retronecine pyrrole 
• 28463-14-1 retronecic acid 
• 480-54-6 retrorsine 

Relevant articles and documents

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Stereoselective Synthesis of the Pyrrolizidine Alkaloids (-)-Integerrimine and (+)-Usaramine

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.