480-82-0

Basic information

• Product Name: Indicin
• Synonyms: Indicin;indicine;(14β,20S)-3β-[(2,6-Dideoxy-β-D-allopyranosyl)oxy]pregn-5-ene-14,20-diol;Calogenin-3-O-β-D-digitoxopyranoside;(2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methyl-butyric acid [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl ester;[(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate;[(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methyl-butanoate
• CAS NO: 480-82-0
• Molecular Formula: C₁₅H₂₅NO₅
• Molecular Weight: 299.3627
• Mol File: 480-82-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 463.3°Cat760mmHg
• Flash Point: 234°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.57E-10mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethanol ()Slightly, Methanol (Slightly)
• CAS DataBase Reference: Indicin(CAS DataBase Reference)
• NIST Chemistry Reference: Indicin(480-82-0)
• EPA Substance Registry System: Indicin(480-82-0)

Safety Data

• Hazardous Substances Data: 480-82-0(Hazardous Substances Data)

Usage

Uses

Indicine is the major pyrrolizidine alkaloid of Heliotropium indicum, one of the most widely used herbs in India. Indicine is a potentially hepatoxic agent and is also used to determine the amount of urinary pregnanediol as a method of ovulation detection in humans.

InChI:InChI=1/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15+/m0/s1

Upstream product

• 72213-98-0 parsonsine 
• 95462-07-0 4(R)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 480-85-3 retronecine 
• 94773-28-1 trans-α-isopropylcrotonic acid 
• 23944-47-0 (+/-)-trachelanthic acid 
• 132585-75-2 (1'S,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one 
• 23944-50-5 (2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 95363-32-9 (4R,5S)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 126331-49-5 (2S,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid 
• 126453-22-3 (2R,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid 
• 20267-93-0 lycopsamine A N-oxide 

Downstream Products

• 41708-76-3 (+)-indicine N-oxide 

Relevant articles and documents

Enantiospecific synthesis of (+)- and (-)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-a and AD-mix-P, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.

Ideamine N-Oxides: Pyrrolizidine Alkaloids Sequestered by the Danaine Butterfly, Idea leuconoe

Two new pyrrolizidine alkaloids, ideamines A and B, together with other analogs (lycopsamine and parsonsine) were isolated in the N-oxide forms from adult bodies of the Apocynaceae-feeding danaine butterfly, Idea leuconoe.Ideamine A was characterized as a homolog of lycopsamine, in which the viridifloric acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety.Likewise, ideamine B was identified as a nor-derivative of parsonsine, in which the trachelanthic acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety diastereomeric to the necic acid from ideamine A.

Total syntheses of indicine N-oxide, intermedine N-oxide, and their enantiomers using carbohydrate as a chiral educt

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