Abietic Acid → Levopimaric acid

HRID 846536

反応式

HRID 846536 の反応式
[CH:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[CH2:9][O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])=[CH:3][CH:2]=1.[CH3:22][CH:23]([C:25]1[CH2:34][CH2:33][C@H:32]2[C:27](=[CH:28][CH2:29][C@H:30]3[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35][C@@:31]32[CH3:43])[CH:26]=1)[CH3:24]>>[CH3:22][C:23]([CH3:24])=[C:25]1[CH:26]=[C:27]2[CH2:28][CH2:29][C@H:30]3[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35][C@:31]3([CH3:43])[C@H:32]2[CH2:33][CH2:34]1.[CH3:24][CH:23]([C:25]1[CH2:34][CH2:33][C:32]2[C@:31]3([CH3:43])[C@@H:30]([CH2:29][CH2:28][C:27]=2[CH:26]=1)[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35]3)[CH3:22].[CH3:24][CH:23]([C:25]1[CH:26]=[C:27]2[CH2:28][CH2:29][C@H:30]3[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35][C@:31]3([CH3:43])[C@H:32]2[CH2:33][CH:34]=1)[CH3:22].[CH:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[CH2:9][O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])=[CH:5][CH:6]=1

参加物

6

反応物 2

HCID 10569Abietic AcidHCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol3 回

生成物 4

HCID 221062Levopimaric acidHCID 221118Neoabietic acidHCID 443613Palustric acidHCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

実験手順

Rosin from the species pinus halepensis was analyzed for content of various types of rosin acids. The rosin had an abietic acid content of 35%, a neoabietic acid content of 15%, a palustric acid content of 17.5% and a levopimaric acid content of 12.5% giving a total of rosin acids having conjugated double bonds of 80%. The rosin was dissolved in toluene to form a 25 to 30% solution. To the solution was added concentrated sulphuric acid, with stirring and cooling. Over 2 hours the temperature rose to 40°-45° C. then fell to about 30° C. The organic and acid phases separated and the organic phase was drawn off. The solvent was removed to yield a hard dimerized rosin having a softening point of from 125° to 130° C.

出典と根拠

ORDレコード
ord-43d93758208b4f3e9fe7b86a172d5187
出典データセット
uspto-grants-1992_08
特許番号
US05137563

関連ノート

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