17233-93-1

Usage

Uses

Used in Pharmaceutical Industry:
Viridifloric acid is used as an intermediate in the synthesis of (+)-Lycopsamine, a compound found in pyrrolizidine alkaloid-containing plants. These plants are known for their hepatotoxic and tumorigenic effects, making viridifloric acid a crucial component in the development of pharmaceuticals targeting liver-related diseases and cancer.
Used in Research and Development:
Viridifloric acid is utilized in research and development for understanding the mechanisms of pyrrolizidine alkaloid-induced liver tumor formation. Its role in the synthesis of (+)-Lycopsamine and its connection to DNA adducts make it an important compound for studying the effects of these poisonous plants on human and animal health.
Used in Toxicology Studies:
Due to its presence in hepatotoxic and tumorigenic plants, viridifloric acid is used in toxicology studies to investigate the effects of pyrrolizidine alkaloids on liver function and tumor development. This helps in understanding the risks associated with exposure to these plants and the potential development of countermeasures or treatments for their toxic effects.

InChI:InChI=1/C7H14O4/c1-4(2)7(11,5(3)8)6(9)10/h4-5,8,11H,1-3H3,(H,9,10)/t5-,7-/m1/s1

Upstream product

• 23944-47-0 (+/-)-trachelanthic acid 
• 94773-28-1 (E)-2-(1-methylethyl)-2-butenoic acid 
• 17132-45-5 (+/-)-trachelanthic acid 
• 6224-43-7 iso-lycopsamine 
• 132585-76-3 (1'R,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one 
• 81816-10-6 4(R)-(1-methylethyl)-2,2,5(R)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 856183-33-0 ethyl 2-(1-methylethyl)but-2-enoate 
• 26131-12-4 isoechinatine 
• 94773-28-1 trans-α-isopropylcrotonic acid 
• 87826-82-2 (4R,5R)-2,2,5-Trimethyl-4-(1-methylethenyl)-1,3-dioxolan-4-carbonsaeure-methylester 
• 87826-83-3 (4R,5R)-2,2,5-Trimethyl-4-(1-methylethyl)-1,3-dioxolan-4-carbonsaeure-methylester 
• 87860-98-8 (4R,5R)-4-(1-Hydroxy-1-methylethyl)-2,2,5-trimethyl-1,3-dioxolan-4-carbonsaeure-methylester 
• 89053-56-5 (2S-cis)-2-(1,1-dimethylethyl)-5-(1-methylethyl)-1,3-dioxolan-4-one 
• 14199-13-4 3-hydroxy-2-isopropyl-butyric acid ethyl ester 

Downstream Products

• 95462-13-8 morifoline 
• 7493-58-5 4-methyl-2,3-pentanedione 

Relevant academic research and scientific papers

ISO-LYCOPSAMINE, A PYRROLIZIDINE ALKALOID FROM HELIOTROPIUM KERALENSE

The pyrrolizidine alkaloids of Heliotropium keralense have been isolatedand characterized.They are iso-lycopsamine, a new pyrrolizidine alkaloid, intermedine and retronecine. iso-Lycopsamine was formulated as 1,2-dehydro-1-hydroxymethyl-7β-(+)-viridifloroxy-8α-pyrrolizidine on the basis of spectroscopic measurements and hydrolysis.

Isoechinatine, a pyrrolizidine alkaloid from Cynoglossum furcatum

The pyrrolizidine alkaloids of Cynoglossum furcatum have been isolated and characterized. They are isoechinatine 1, a new pyrrolizidine ester alkaloid, echinatine, neocoramandaline and a free necine heliotridine. Isoechinatine is formulated as 9-(O)-(+)-viridiflorylheliotridine. 3-Hydroxy 6-methylpyridine has also been isolated and characterized.

Absolute configuration and synthesis of β- and δ-lactones present in the pheromone system of the giant white butterfly Idea leuconoe

Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the β-lactones la and lb is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the δ-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents

(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine (2) obtained by hydrolysis of monocrotaline (1), isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine (7), intermedine (13), lycopsamine (15), and the new nonnatural product 16, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.

Stereoselective Synthesis of Alcohols, XV. Stereoselective Synthesis of α-Alkyl-α,β-dihydroxycarboxylic Ester Derivatives: Synthesis of (+)-Viridifloric Acid

Reaction of the alkyl 1,3-dioxolan-4-carboxylates 2 with lithium diisopropylamide generated the enolates 3 which on reaction with methyl iodide yielded the products 4 (favoured) and 5.The reaction of the enolate (+)-3e with acetone under thermodynamic con

MINOR ALKALOIDS OF HELIOTROPIUM CURASSAVICUM

Isolation and structure determination of the minor alkaloids of Heliotropium curassavicum are described.These include the new pyrrolizidine alkaloids, heliocurassavine , heliocoromandaline , heliocurassavicine , heliocurassavinine , curassavinine , coromandalinine , heliovinine and curassanecine .Structures were established by high resolution 1H NMR, mass spectrometry and paper electrophoresis of the alkaloids and their hydrolysis products. - Key Word Index-Pyrrolizidine alkaloids; heliocurassavine; heliocurassavinine; heliocurassavicine; heliocoromadaline; curassavinine; coromandalinine; heliovinine; curassanecine.