480-83-1

Usage

Uses

Used in Pharmaceutical Industry:
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1alpha,7(2R,3R),7aal pha]]is used as an active pharmaceutical ingredient for the development of new drugs. Its unique chemical structure allows it to interact with specific biological targets, potentially leading to the development of novel therapeutic agents.
Used in Chemical Research:
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1alpha,7(2R,3R),7aal pha]]is also used in chemical research as a starting material or intermediate for the synthesis of more complex molecules. Its reactivity and functional groups make it a valuable tool for exploring new chemical reactions and developing innovative synthetic pathways.
Used in Cosmetics Industry:
Due to its unique chemical structure and potential reactivity, Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1alpha,7(2R,3R),7aal pha]]may also find applications in the cosmetics industry. It could be used as a key component in the formulation of new cosmetic products, such as skincare or hair care products, where its unique properties may provide specific benefits to the consumer.
Used in Agrochemical Industry:
In the agrochemical industry, Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro- 1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1alpha,7(2R*,3R*),7aal pha]]- may be utilized as a precursor for the development of new pesticides or other agricultural chemicals. Its unique structure and reactivity could potentially be harnessed to create novel products that address specific needs in the agricultural sector.

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

Synthetic route

<1,4-14C2>Putrescine dihydrochloride (69102-07-4) + (+/-)-<5-3H>isoretronecanol (102731-60-2) → (+)-Echinatine (480-83-1)

Conditions	Yield
In water for 168h; feeding by absorption through stem punctures to Cynoglossum officinale, 3H/14C ratio;

<1,4-14C2>Putrescine dihydrochloride (69102-07-4) + (+/-)-<5-3H>trachelanthamidine (102731-60-2) → (+)-Echinatine (480-83-1)

Conditions	Yield
In water for 168h; feeding by absorption through stem punctures to Cynoglossum officinale, 3H/14C ratio;

(+)-Echinatine (480-83-1) → (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (17132-48-8) + (+)-heliotridine (520-63-8)

Conditions	Yield
With barium dihydroxide	A 4% B 99%
With barium dihydroxide In water for 4h; Heating;	A 80% B 85%

methanol (67-56-1) + (+)-Echinatine (480-83-1) + platinum → erythro-2.3-dihydroxy-2-isopropyl-butyric acid (466-18-2, 17132-45-5, 17132-48-8, 17233-93-1, 23944-47-0, 23944-48-1, 23944-50-5) + heliotridan-7α-ol

Conditions	Yield
Hydrogenation;

sulfuric acid (7664-93-9) + (+)-Echinatine (480-83-1) + platinum → erythro-2.3-dihydroxy-2-isopropyl-butyric acid (466-18-2, 17132-45-5, 17132-48-8, 17233-93-1, 23944-47-0, 23944-48-1, 23944-50-5) + heliotridan-7-α-ol

Conditions	Yield
Hydrogenation;

(+)-Echinatine (480-83-1) → (+)-7,9-O,O'-(3,3-Pentamethyleneglutaryl)heliotridine (117565-67-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

(+)-Echinatine (480-83-1) → (+)-7,9-O,O'-(Glutaryl)heliotridine (117605-56-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

(+)-Echinatine (480-83-1) → 7,9-O,O'-<(2S,4R)-Dimethylglutaryl>heliotridine (108913-56-0, 109009-00-9, 117605-57-9, 117605-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

(+)-Echinatine (480-83-1) → 7,9-O,O'-<(2R,4S)-Dimethylglutaryl>heliotridine (108913-56-0, 109009-00-9, 117605-57-9, 117605-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

(+)-Echinatine (480-83-1) → (+)-7,9-O,O'-(3,3-Dimethylglutaryl)heliotridine (114817-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

(+)-Echinatine (480-83-1) → (+)-7,9-O,O'-(3,3-Tetramethyleneglutaryl)heliotridine (117605-55-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / barium hydroxide / H2O / 4 h / Heating 2: 1.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) DME, 48 h, 2.) reflux 14 h View Scheme

Upstream product

• 69102-07-4 <1,4-14C2>Putrescine dihydrochloride 
• 102731-60-2 (+/-)-<5-3H>isoretronecanol 
• 102731-60-2 (+/-)-<5-3H>trachelanthamidine 
• 72213-98-0 parsonsine 
• 20267-93-0 lycopsamine A N-oxide 

Downstream Products

• 466-18-2 erythro-2.3-dihydroxy-2-isopropyl-butyric acid 
• 17132-48-8 (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 520-63-8 (+)-heliotridine 

Relevant academic research and scientific papers

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.

Pyrrolizidine Alkaloid Biosynthesis. Synthesis of 3H-Labelled Trachelanthamidine and Isoretronecanol and their Incorporation into Three Pyrrolizidine Bases (Necines)

(+/-)-Isoretronecanol (22) and (+/-)-trachelanthamidine (24) were prepared by 1,3-dipolar cycloaddition of N-formylproline with ethyl propiolate followed by reduction steps.These 3H-labelled 1-hydroxymethylpyrrolizidines together with putrescine were fed to Senecio isatideus which produces retrorsine (1); S. pleistocephalus which yields rosmarinine (8); and Cynoglossum officinale which affords echinatine (5).The double labelling experiments demonstrated that isoretronecanol is incorporated much more efficiently into rosmarinine than into retrorsine or echinatine, whereas trachelanthamidine is a much more efficient precursor for retrorsine and echinatine.Base hydrolysis of retrorsine and echinatine labelled with trachelanthamidine and of rosmarinine labelled with isoretronecanol established that most of the 3H-label was in the base portions, retronecine (2), heliotridine (6), and rosmarinecine (9), respectively.Further degradation of retronecine and rosmarinecine showed that most of the radioactivity was confined to the β-alanine (4) portion.The biosynthetic pathways to isoretronecanol and trachelanthamidine apparently diverge prior to the formation of these 1-hydroxymethylpyrrolizidines, probably during the cyclisation of an immonium ion (14) to form the 1-formylpyrrolizidines (15) and (17).