480-82-0

Usage

Uses

Used in Pharmaceutical Applications:
Indicin is used as a hepatotoxic agent for its potential effects on liver function. This characteristic makes it a valuable compound for research and pharmaceutical development, particularly in understanding liver-related conditions and their treatment.
Used in Fertility and Ovulation Detection:
Indicin is used as a biomarker for determining the amount of urinary pregnanediol, which serves as a method of ovulation detection in humans. This application aids in fertility studies and assists in the development of ovulation detection tools and treatments for infertility.

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

• 20267-93-0 lycopsamine A N-oxide 
• 126453-22-3 (2R,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid 
• 480-85-3 retronecine 
• 126331-49-5 (2S,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic 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 
• 95462-07-0 4(R)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 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 
• 72213-98-0 parsonsine 

Downstream Products

• 41708-76-3 (+)-indicine N-oxide 

Relevant academic research and scientific papers

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.

An Efficient Enantioselective Synthesis of Indicine N-Oxide, an Antitumor Pyrrolizidine Alkaloid

Indicine N-oxide (1), a pyrrolizidine alkaloid potentially useful for an anticancer drug was synthesized in the natural form through regioselective coupling of (+)-retronecine (2) and the protected necic acids 16a and 16b, the latter being efficiently prepared from the optically pure lactone 5.

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.

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.