ANGELIC ANHYDRIDE

Base Information

• Chemical Name: ANGELIC ANHYDRIDE
• CAS No.: 94487-74-8
• Molecular Formula: C10H14 O3
• Molecular Weight: 182.22
• Hs Code.: 2916190090
• Mol file: 94487-74-8.mol

Synonyms:2-Butenoicacid, 2-methyl-, anhydride, (Z,Z)- (9CI); Angelic anhydride (7CI)

Chemical Property of ANGELIC ANHYDRIDE

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.464
• Boiling Point: 108 °C / 13mmHg
• Flash Point: 119.788°C
• PSA: 43.37000
• Density: 1,02 g/cm3
• LogP: 1.98860
• Storage Temp.: 0-10°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Angelic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Angelic Anhydride is a reagent in the improved synthesis of angelate esters, which are the active chemical behind the strong pain-relieving and spasmolytic action of extracts from the plant butterbur.

Technology Process of ANGELIC ANHYDRIDE

There total 4 articles about ANGELIC ANHYDRIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Angelic acid (565-63-9) → (Z)-2-methyl-2-butenoic anhydride (94487-74-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; xylene; at 20 ℃; for 1h;

Reference yield:

Angelic acid (565-63-9) + (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one (77573-43-4) → (Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (E)-2-methyl-2-butenoic anhydride (14316-68-8) + AngOTig (1356334-21-8) + ingenol-5,20-acetonide-3-tiglate (1356490-35-1,87980-68-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

Reference yield:

Angelic acid (565-63-9) + (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one (77573-43-4) → (Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (E)-2-methyl-2-butenoic anhydride (14316-68-8) + AngOTig (1356334-21-8) + ingenol-5,20-acetonide-3-tiglate (1356490-35-1,87980-68-5) + 3-O-angeloyl-5,20-O-isopropylideneingenol (87980-68-5)

Guidance literature:

With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide; In toluene; at 60 ℃; for 18h;

upstream raw materials:

Angelic acid

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

Downstream raw materials:

ingenol mebutate

ingenol-3-tigliate

3-O-angeloyl-5,20-O-isopropylideneingenol

ingenol-5,20-acetonide-3-tiglate

Refernces

• 1、 Liang, Xifu,Grue-Sorensen, Gunnar,Petersen, Anders Klarskov,H?gberg, Thomas. "Semisynthesis of ingenol 3-angelate (PEP005): Efficient stereoconservative angeloylation of alcohols". supporting information. p. 2647 - 2652. Retrieved 2013/01/15.