GB585828A - Improvements in or relating to the production of monoesters of isoascorbic acid - Google Patents

Improvements in or relating to the production of monoesters of isoascorbic acid

Info

Publication number
GB585828A
GB585828A GB15212/43A GB1521243A GB585828A GB 585828 A GB585828 A GB 585828A GB 15212/43 A GB15212/43 A GB 15212/43A GB 1521243 A GB1521243 A GB 1521243A GB 585828 A GB585828 A GB 585828A
Authority
GB
United Kingdom
Prior art keywords
acid
isoascorbic
isoascorbic acid
hours
esters
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB15212/43A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Hoffmann La Roche Inc
Original Assignee
F Hoffmann La Roche AG
Hoffmann La Roche Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG, Hoffmann La Roche Inc filed Critical F Hoffmann La Roche AG
Publication of GB585828A publication Critical patent/GB585828A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62—Three oxygen atoms, e.g. ascorbic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Fat soluble isoascorbyl esters are especially valuable as anti-oxidants for edible fats.ALSO:Esters of isoascorbic acid containing an unsubstituted ene-diol group are prepared by reacting isoascorbic acid with a saturated aliphatic monocarboxylic acid in the presence of concentrated sulphuric acid as an esterification catalyst and solvent for the reaction products, or with acyl halides derived from such monocarboxylic acids. The preferred strength of the sulphuric acid is about 95 per cent, since at this concentration it is especially adapted for performing the dual function of esterification catalyst and solvent. In examples: (1) d-isoascorbic acid is esterified by treatment at room temperature with lauric acid in the presence of 95 per cent sulphuric acid for about 6 hours. The reaction mixture is poured slowly on to ice, extracted with ether, evaporated and dried, and finally washed with petroleum ether; (2) d-isoascorbic acid is heated with palmitoyl chloride for six hours at 75 DEG C. The product is extracted with hot water, cooled and filtered; (3) d-isoascorbic acid is heated with myristoyl chloride in the presence of pyridine at 50 DEG C. for two hours. d-Isoascorbic acid is esterified as described in example (1), with (4) myristic acid; (5) palmitic acid; (6) stearic acid; (7) caproic acid; (8) 9 : 10-dihydroxystearic acid. It is stated that an important result of the process of the present invention is that the esters formed retain the characteristic properties of compounds containing an unsubstituted enediol group. The compounds of the invention have valuable anti-oxidant properties and are particularly suitable as anti-oxidants for edible fats.
GB15212/43A 1942-05-11 1943-09-16 Improvements in or relating to the production of monoesters of isoascorbic acid Expired GB585828A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US585828XA 1942-05-11 1942-05-11

Publications (1)

Publication Number Publication Date
GB585828A true GB585828A (en) 1947-02-26

Family

ID=22017723

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15212/43A Expired GB585828A (en) 1942-05-11 1943-09-16 Improvements in or relating to the production of monoesters of isoascorbic acid

Country Status (1)

Country Link
GB (1) GB585828A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1239682B (en) * 1962-11-14 1967-05-03 Hoffmann La Roche Process for the preparation of 6-O-ascorbic acid and isoascorbic acid monooleate
US4151178A (en) * 1976-10-05 1979-04-24 Kansas State University Research Foundation Method of synthesizing fatty acid esters of ascorbic acid
EP0182934A1 (en) * 1984-11-29 1986-06-04 Frisco-Findus Ag Surfactants
CN110128381A (en) * 2019-06-14 2019-08-16 河北美荷药业有限公司 A kind of preparation method of ascorbyl laurate

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1239682B (en) * 1962-11-14 1967-05-03 Hoffmann La Roche Process for the preparation of 6-O-ascorbic acid and isoascorbic acid monooleate
US4151178A (en) * 1976-10-05 1979-04-24 Kansas State University Research Foundation Method of synthesizing fatty acid esters of ascorbic acid
EP0182934A1 (en) * 1984-11-29 1986-06-04 Frisco-Findus Ag Surfactants
CN110128381A (en) * 2019-06-14 2019-08-16 河北美荷药业有限公司 A kind of preparation method of ascorbyl laurate

Similar Documents

Publication Publication Date Title
US3714144A (en) Process for the production of sucrose esters of fatty acids
US2350435A (en) Derivatives of ascorbic acid
GB585828A (en) Improvements in or relating to the production of monoesters of isoascorbic acid
US2938027A (en) Process of preparing esters of acetyl tartaric and citric acids
US2523309A (en) Preparation of diglycerides
GB903613A (en) Improvements in or relating to the production of acetoacetic acid esters
US2408897A (en) Derivatives of isoascorbic acid
GB579333A (en) Improvements in or relating to the production of monoesters of ascorbic acid
US2454748A (en) Ascorbic acid tetraester preparation
US2126460A (en) Preparation of cellulose esters containing dicarboxylic acid radicals
DE915566C (en) Process for the preparation of N-acylated amino sugars
US2408182A (en) Derivatives of isoascorbic acid
US2232433A (en) Method of preparing terpin esters
GB783463A (en) Esters purification process
US2032749A (en) Esterification of cellulose
US2022446A (en) Process of preparing organic cellulose esters
US2758998A (en) Process for preparing citrazinamide
US1909388A (en) Production of tetra-acyl-glycocholyl thujylamines
SU371217A1 (en) WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20
US3555088A (en) Plicatyl hydrazide
US1701229A (en) Ucts therefrom
US3644481A (en) Plicatic acid esters
SU405871A1 (en) METHOD OF OBTAINING COMPLEX ETHER OF SALICILYLIDE
US3799958A (en) Ester synthesis for preparation of specific glycerides
SU31430A1 (en) Linatiole acetylation method