The PROBABLE IDENTITY OF Α- AND Β-Linoleic ACIDS

Riemenschneider, R. W.; Wheeler, D. H.; Sando, Charles E.

doi:10.1016/s0021-9258(18)73791-5

Cited by 28 publications

(8 citation statements)

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“…Riemenschneider et al (7) concluded that bromination of cis-9-cis-12-octade- This conclusion was supported by previous observations that bromine adds to a double bond exclusively by cis-addition or by trans-addition. Applying the same arguments to the oxidation of -linoleic acid, they concluded that alkaline potassium permanganate oxidation or peracetic acid oxidation would give only two racemates of 9,10,12,13-tetrahydroxystearic acid.…”

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confidence: 73%

“…trans-9,10-Dihydroxy-lS-octadecenoic acid (XVIII). 12,13-Dibromo-9-octadecenoic acid (39.0 g.; 0.088 mole) was oxidized in dilute alkaline solution with potassium permanganate by the method of Riemenschneider et al (7). The product was recovered by extracting the decolorized and acidified permanganate solution with ether (3 X 400 cc.).…”

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confidence: 99%

“…Alkaline potassium permanganate oxidation of trans-9,10-dihydroxy-12-octadecenoic acid. Eighty-nine milligrams (0.00027 mole) of trans-9,10-dihydroxy-12-octadecenoic acid (m. p. 97°) was oxidized with aqueous alkaline permanganate solution using the method of Riemenschneider et al (7). The crude product after filtration from the acidified and decolorized potassium permanganate solution melted at 138-149°, yield 55 mg., or 55.8%.…”

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The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

McKay¹,

Bader²

1948

J. Org. Chem.

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The eight diastereoisomers of 9,10,12,13-tetrahydroxystearic acid were prepared from a -linoleic acid (cis-9-cis-12-octadecadienoic acid). A new method of preparation was developed which establishes the spacial relationships of the hydroxyl groups in each diastereoisomer.Hazura (1) was the first to isolate a 9,10,12,13-tetrahydroxystearic acid (sativic acid) from the alkaline potassium permanganate oxidation of linoleic acid.Further study (2)(3)(4)(5)(6) of this oxidation reaction resulted in methods for improving the yield and it is now established that two diastereoisomers of the tetrahydroxystearic acid are formed in this reaction. The melting points of these acids are 173°( I) and 164°( II). The more soluble one has also been reported to melt at 157-159°, but according to Riemenschneider et al. ( 7) this is an eutectic mixture of the «-and jS-sativic1 acids melting at 173°and 164°. Nicolet and Cox (8) obtained two different diastereoisomers of 9,10,12,13-tetrahydroxystearic acid by treating linoleic acid with hypochlorous and hypobromous acids to form the dichloroand dibromo-dihydroxystearic acids. Replacement of the halogen atoms by hydroxyl groups gave two tetrahydroxystearic acids melting at 145°a nd 135°. Later work suggests that these acids are the same as the two diastereoisomers obtained in the peracetic acid oxidation of linoleic acid (9), or the alkaline potassium permanganate oxidation of linolelaidic acid (10) which are now described as melting at 146°( III) and 126°or 122°( IV). Kass and Burr (10) prepared a third set of diastereoisomers of 9,10,12,13-tetrahydroxystearic acid by the alkaline potassium permanganate oxidation of the trans-cis or cis-trans geometric isomer of linoleic acid. The melting points of these acids are given as 156-158°( V) and 126°( VI). The melting point of the former has now been raised to 164°. A seventh diastereoisomer of tetrahydroxystearic acid was re-1. A method is described for the preparation of the eight diastereoisomers of 9,10,12,13-tetrahydroxystearic acid from -linoleic acid. The special arrangements of the hydroxyl groups in each diastereoisomer are deduced from this method of preparation.2. Two new fatty acids cis-and trans-9,10-dihydroxy-12-octadecenoic acid are also described.3. The present system of nomenclature applied to the tetrahydroxystearic acids is discussed.

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The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

McKay¹,

Bader²

1948

J. Org. Chem.

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“…This was shown by melting point, neutral equivalent and elementary analysis to be one of the high melting forms of 9,10,12,13-tetrahydroxystearic (sativic) acid. 16 Thus from three runs there was obtained, in addition to 13 g. of 9,10-dihydroxystearic acid (m. p., 129-30°), 2.0 g. of sativic acid melting at 172-173°.…”

Section: Methodsmentioning

confidence: 99%

Hydroxylated Stearic Acids. II. The Periodate Oxidation of the 9,10-Dihydroxystearic Acids and the 1,9,10-Trihydroxyoctadecanes^1a

Wittcoff¹,

Moe²,

Iwen³

1948

J. Am. Chem. Soc.

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“…Vidyarthi and Mallya (265) have also contributed to the component glyceride analysis of similar liquid fats by a systematic examination of (debrominated) products obtained from fractions of brominated glycerides separated from suitable solvents,-a procedure which was also suggested, but not reported upon in detail, by Gunde and Hilditch (88). A limitation of the latter method which has not received due consideration is the known incomplete and variable separation of unsaturated components as bromine addition products (22,37,82,111,214,230,232).…”

Section: Component Glycerides Of Natural Fatsmentioning

confidence: 99%

Composition and Structural Characteristics of Glycerides in Relation to Classification and Environment.

Longenecker¹

1941

Chem. Rev.

112

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The PROBABLE IDENTITY OF Α- AND Β-Linoleic ACIDS

Cited by 28 publications

References 10 publications

The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

Hydroxylated Stearic Acids. II. The Periodate Oxidation of the 9,10-Dihydroxystearic Acids and the 1,9,10-Trihydroxyoctadecanes^1a

Composition and Structural Characteristics of Glycerides in Relation to Classification and Environment.

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The PROBABLE IDENTITY OF Α- AND Β-Linoleic ACIDS

Cited by 28 publications

References 10 publications

The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

The Preparation and Properties of the Eight Diastereoisomers of 9,10,12,13-Tetrahydroxystearic Acid

Hydroxylated Stearic Acids. II. The Periodate Oxidation of the 9,10-Dihydroxystearic Acids and the 1,9,10-Trihydroxyoctadecanes1a

Composition and Structural Characteristics of Glycerides in Relation to Classification and Environment.

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Hydroxylated Stearic Acids. II. The Periodate Oxidation of the 9,10-Dihydroxystearic Acids and the 1,9,10-Trihydroxyoctadecanes^1a