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

Description

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 a complex organic compound with a unique chemical structure. It is characterized by its ester functional group and the presence of multiple hydroxyl groups, which contribute to its potential reactivity and applications in various fields.

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, this compound 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 
• 20267-93-0 lycopsamine A N-oxide 
• 72213-98-0 parsonsine 

Downstream Products

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

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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