Cholesterol → Palmitic Acid

HRID 1445318Notes

Reaction equation

[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:29]([OH:48])(=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[C:29]([OH:48])(=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[C:29]([OH:48])(=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

Reactant 2

HCID 5997Cholesterol3×

HCID 445639Oleic Acid

Product 3

HCID 985Palmitic Acid

HCID 5997Cholesterol

HCID 445639Oleic Acid

Procedure

The 13C NMR spectrum of BBGL-II displayed 59 major, resolved resonances, of which five were due to quaternary 13C nuclei, i.e., not detected by 13C DEPT experiments. From low field to high field (Table III), the five quaternary 13C resonances were assigned as two ester carbonyl resonances, and C-5 (olefinic), C-13, and C-10 resonances of the cholesterol moiety. Of the total number of 13C resonances, 15 could be identified as CH by DEPT spectrum editing (FIG. 3a), together with 27 CH2 and six CH3 groups (FIG. 3b). Five of the CH3 resonances were assigned to the cholesterol residue (Table III), and the sixth, weaker one at δC 14.13 to a combination of the signals of the ω methyl carbons of fatty acid ester groups, which typically may not be resolved from each other. The two major olefinic CH resonances at ˜130 ppm were assigned to a predominant, unsaturated fatty acid ester group (oleic acid, 18:1), although additional weaker resonances in that region indicated the presence of minor proportions of other unsaturated fatty acid ester groups. The CH resonances at 122.12 and 79.46 ppm were assigned to C-6 and C-3 of the cholesterol moiety, respectively. Good agreement was obtained between the 13C chemical shifts of BBGL-II and those of its lipid components, cholesterol, palmitic acid, and oleic acid, except for nuclei near the points of attachment of the residues (Table III). The 13C assignments for cholesterol in chloroform-d solution are based on those reported (24) for a pyridine-d5 solution, while ensuring that the assignments were consistent with the results of the DEPT experiments.

Sources & evidence

ORD record: ord-53b76a888f334cb4b8ed30f1aaa442e5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666846B2

Reaction notes

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