950. The relation between dextro- and isodextro-pimaric acid

Green, B.; Harris, Adelaide; Whalley, W. B.

doi:10.1039/jr9580004715

Cited by 10 publications

(4 citation statements)

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“…The -lactones obtained by the treatment with concentrated sulfuric acid of dihydrodextropimaric and dihydroisodextropimaric acids are obviously different. These results clearly indicate that dextroand isodextropimaric acids are epimeric at C-7 at least (64,99).…”

Section: Stereochemistrymentioning

confidence: 70%

Diterpenoids

Tsutsui¹,

Tsutsui²

1959

Chem. Rev.

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Section: Stereochemistrymentioning

confidence: 70%

Diterpenoids

Tsutsui¹,

Tsutsui²

1959

Chem. Rev.

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“…The title compound has been isolated from a mixture of resin acids. It was identified as pimaric acid on the basis of the comparison of its physical and spectral data with literature values (Green et al, 1958;Harris et al, 1948). Pimaric acid exhibits a wide range of biological activities such as trypanocidal activity (Rubio et al, 2005), potent BK channel activity (Imaizumi et al, 2002).…”

Section: S1 Commentmentioning

confidence: 99%

1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Chen

Zhao

et al. 2009

Acta Cryst E

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“…T h e rotatory dispersion observations of Bose and Strz~ck (7) provide a n i~~~p o r t a n t addition to the body of evidence (6, 8,8 ) For personal use only.…”

Section: Hooc' Hooc' Hooc"mentioning

confidence: 99%

The Structure of Sandaracopimaric Acid

Edwards¹,

Nicolson²,

Rodger³

1960

Can. J. Chem.

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Sandaracopi~naric acid has been shown to be 7-epipimara-8(14),18-dienoic acid (II), and Ukita's acid to be T-epi-13p-pin1ara-9(14),18-dienoic acid (VI). A hydroxyl-containing acid from Sandarac resin is described.Sandaracopimaric acid was isolated by Henry (1) and by Tschirch and Wolff (2) from the resin of the N. African sandarac tree (Callitris qz~adrivalvis). Recently an improved isolation procedure was described by Petru and Galilc ( 3 ) , who also demonstrated that the acid belonged to the pi~naric group. They claimed (4) that both pimaric acid and sandaracopilnaric acid gave the sanle partial dehydrogenatio~l product I and hence had the sanle configuration at C-7. Even if this conclusion had been correct their xvorlc left the location of the double bond and the stereoche~nistry a t the other a s y~n~n e t r i c centers unlcnown. I n continuance of our interest in the stereochemistry of the pi~naric acids3 we have examined sandaracopirnaric acid, and proved it to be the C-7 epi~ner (11) of pimaric acid (7-epipimara-8(14) ,18-dienoic acid) .4Using the ~nethocl of Petru and Galilc (3) we obtained an ether-soluble anlrnoniu~n salt fro111 the resin. This was co~lverted into the sodium salt, which was then precipitated from its aqueous solution by addition of concentrated sodium hydroxide solution. The precipitate did not crystallize readily, so the acids liberated from it were chromatographed on silica gel. In this way a 2.2% yield of sandaracopimaric acid and a 1.3% yield of a higher ~nelting acid were obtained. The latter had m.p. 270" and [a],, -11" in ethanol.\

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950. The relation between dextro- and isodextro-pimaric acid

Cited by 10 publications

References 0 publications

Diterpenoids

Diterpenoids

1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

The Structure of Sandaracopimaric Acid

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