17233-93-1

Basic information

• Product Name: viridifloric acid
• Synonyms: viridifloric acid;[2R,3R,(+)]-2,3-Dihydroxy-2-isopropylbutanoic acid
• CAS NO: 17233-93-1
• Molecular Formula: C₇H₁₄O₄
• Molecular Weight: 162.18
• Mol File: 17233-93-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 119-121 °C(Solv: chloroform (67-66-3))
• Boiling Point: 331.7°Cat760mmHg
• Flash Point: 168.6°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.491
• PKA: 3.68±0.25(Predicted)
• CAS DataBase Reference: viridifloric acid(CAS DataBase Reference)
• NIST Chemistry Reference: viridifloric acid(17233-93-1)
• EPA Substance Registry System: viridifloric acid(17233-93-1)

Safety Data

• Hazardous Substances Data: 17233-93-1(Hazardous Substances Data)

Usage

Uses

(2R,3R)-Viridifloric Acid is an intermediate in the synthesis of (+)-Lycopsamine (L487525), which occurs in pyrrolizidine alkaloid-containing plants, which are the most common poisonous plants affecting livestock, wildlife, and humans. They are being known as hepatotoxins and tumorigens.It has been shown that pyrrolizidine Alkaloid-Derived DNA Adducts, are the common biological biomarker of pyrrolizidine alkaloid-induced liver tumor formation.

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 
• 856183-33-0 ethyl 2-(1-methylethyl)but-2-enoate 
• 67-56-1 methanol 
• 480-83-1 (+)-Echinatine 
• 7664-93-9 sulfuric acid 
• 903507-51-7 heliovicine 
• 903507-51-7 coromandaline 
• 561-34-2 (-)-threo-2-hydroxy-3-methoxy-2-isopropyl-butyric acid 
• 10035-10-6 hydrogen bromide 
• 14199-13-4 3-hydroxy-2-isopropyl-butyric acid ethyl ester 
• 89053-56-5 (2S-cis)-2-(1,1-dimethylethyl)-5-(1-methylethyl)-1,3-dioxolan-4-one 
• 87860-98-8 (4R,5R)-4-(1-Hydroxy-1-methylethyl)-2,2,5-trimethyl-1,3-dioxolan-4-carbonsaeure-methylester 
• 87826-83-3 (4R,5R)-2,2,5-Trimethyl-4-(1-methylethyl)-1,3-dioxolan-4-carbonsaeure-methylester 
• 87826-82-2 (4R,5R)-2,2,5-Trimethyl-4-(1-methylethenyl)-1,3-dioxolan-4-carbonsaeure-methylester 

Downstream Products

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

Relevant articles and documents

Stereoselective synthesis of (-)-trachelanthic acid and (+)-viridifloric acid, necic acid components of pyrrolizidine alkaloids from a common intermediate

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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.

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.