Notes: The Synthesis of Esters of Angelic Acid

1960 ◽  
Vol 25 (12) ◽  
pp. 2217-2218 ◽  
Author(s):  
S. Morris Kupchan ◽  
Adriano Afonso
Keyword(s):  
Angelic Acid

Isolation and identification of a new conjugated carbofuran metabolite in carrots: angelic acid ester of 3-hydroxycarbofuran

1981 ◽  
Vol 29 (6) ◽  
pp. 1125-1129 ◽  
Author(s):  
Hiromi Sonobe ◽  
LaVerne R. Kamps ◽  
Eugene P. Mazzola ◽  
John A. G. Roach
Keyword(s):  
Acid Ester ◽  
Isolation And Identification ◽  
Angelic Acid

Piptoside, a novel alkali-labile glucoside from Piptocalyx moorei Oliv.

1966 ◽  
Vol 19 (4) ◽  
pp. 683 ◽  
Author(s):  
NV Riggs ◽  
JD Stevens
Keyword(s):  
Periodate Oxidation ◽  
Aqueous Sodium Hydroxide ◽  
Carbon Chain ◽  
Hydroxyl Group ◽  
Reaction Products ◽  
Spectroscopic Information ◽  
Michael Type Addition ◽  
Angelic Acid ◽  
Methyl Derivatives ◽  
Fission Yields

The β-D-glucopyranoside, piptoside, is cleaved by hot dilute acid to glucose and aglucone, the latter being partly converted with loss of carbon dioxide into a furan keto acid. Glucose is also liberated by the action of bases. With sodium methoxide, the aglucone residue rearranges to a pair of isomeric dilactone esters, whereas, with aqueous sodium hydroxide, fission of the carbon chain to (-)-2,3-dimethylsuccinic acid occurs; with alkaline hydrogen peroxide, oxidative chain fission yields a buty- rolactone-4,4-dicarboxylic acid. The structure and partial stereochemistry of each of the products follows from chemical and spectroscopic information. These results, as also those of periodate oxidation, are accounted for by formulation of the aglucone as a system of two spiro-joined γ-lactone rings, one of which is fused to a ketofuranose ring. The reaction products are analogous to well-known products from simple sugars. The hemiacetal hydroxyl group of the ketofuranose remains free in the glucoside and is unusally acidic towards diazomethane, the methyl derivatives not being alkalilabile.��� Biogenesis of the aglucone may follow Michael-type addition of a 3-dehydrohexonic acid (of unknown stereochemistry) to angelic acid, or some variant.

The alkaloids of Echium plantagineum L

1956 ◽  
Vol 9 (4) ◽  
pp. 512 ◽  
Author(s):  
CCJ Culvenor
Keyword(s):  
Carboxylic Acid ◽  
Hydroxyl Group ◽  
Angelic Acid

Two new alkaloids, echiumine, C20H31O6N, and echimidine, C20H31O7N, have been isolated from Echium plantagineum L. Both have a retronecine nucleus esterified on the 7-hydroxyl group with angelic acid. The main esterifying acid of echiumine is trachelanthic acid and of echimidine is 2-methyl-2,3,4-trihydroxypentane-3-carboxylic acid, identical with the esterifying acid of heliosupine. The structure of heliosupine, a diastereoisomer of echimidine, has been confirmed.

The biosynthesis of angelic acid in Cynoglossum officinale

1979 ◽  
Vol 18 (10) ◽  
pp. 1647-1649 ◽  
Author(s):  
Brian A. Mcgaw ◽  
Jack G. Woolley
Keyword(s):  
Cynoglossum Officinale ◽  
Angelic Acid

The Ultraviolet-induced Isomerization of Tiglic Acid to Angelic Acid

1952 ◽  
Vol 74 (24) ◽  
pp. 6292-6293 ◽  
Author(s):  
S. W. Pelletier ◽  
William L. McLeish
Keyword(s):  
Tiglic Acid ◽  
Angelic Acid
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