480-83-1

Basic information

• Product Name: 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]]-
• Synonyms: 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]]-;ECHINATINE;(2S,3S)-2,3-Dihydroxy-2-isopropylbutyric acid [(5R,6S)-6-hydroxy-1-azabicyclo[3.3.0]oct-3-en-4-yl]methyl;(2S,3S)-2,3-Dihydroxy-2-isopropylbutyric acid [(5R,6S)-6-hydroxy-1-azabicyclo[3.3.0]oct-3-en-4-yl]methyl ester;Echitine
• CAS NO: 480-83-1
• Molecular Formula: C₁₅H₂₅NO₅
• Molecular Weight: 299.36
• Mol File: 480-83-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 463.3°C at 760 mmHg
• Flash Point: 234°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.57E-10mmHg at 25°C
• Refractive Index: 1.567
• PKA: 12.59±0.29(Predicted)
• CAS DataBase Reference: 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]]-(CAS DataBase Reference)
• NIST Chemistry Reference: 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]]-(480-83-1)
• EPA Substance Registry System: 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]]-(480-83-1)

Safety Data

• Hazardous Substances Data: 480-83-1(Hazardous Substances Data)

Usage

Uses

(+)-Echinatine is a pyrrolizidine alkaloid found in some medicinal herb preparations such as Asmachilca, which is a Peruvian preparation contributing to bronchodialtion and other protoxic effects. However these alkaloids are generally toxic in regards to human consumption.

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

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

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 articles and documents

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.

Unusual macrocyclic pyrrolizidine alkaloids from Parsonsia heterophylla A. Cunn and Parsonsia spiralis Wall (Apocynaceae)

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