NMR of sterols and sphingolipids

Extensive 1H and 13C NMR data for sterols and sphingolipid bases are presented in the following papers:

Wilson, W.K., Sumpter, R.M., Warren, J.J., Rogers, P.S., Ruan, B., and Schroepfer, G.J., Jr., Analysis of unsaturated C27 sterols by nuclear magnetic resonance spectroscopy, J. Lipid Res. 37, 1529-1555 (1996).

Kisic, A., Tsuda, M., Kulmacz, R.J., Wilson, W.K., and Schroepfer, G.J., Jr., Sphingolipid bases. A revisitation of the O-methyl derivatives of sphingosine. Isolation and characterization of diacetate derivatives, with revised 13C nuclear magnetic resonance assignments for D-erythro-sphingosine, J. Lipid Res. 36, 787-803 (1995).

 

Some useful NMR data for unsaturated sterols are also given below.

1H NMR chemical shifts of unsaturated sterols

Data updated to July 1997

Chemical shifts from 500-MHz spectra collected at 25 degrees C, in dilute CDCl3 solution (generally <10 mM)

C27 free sterols

Double bond

H-18

H-19

H-21

D0

.647

.802

.897

D4

.677

1.048

.900

D5 (cholesterol)

.678

1.008

.914

D6

.691

.780

.906

D7

.534

.796

.920

D8

.609

.950

.923

D8(14)

.840

.689

.929

D14

.899

.822

.910

D4,6

.725

.997

.909

D5,7

.620

.946

.941

D5,8

.652

1.188

.934

D5,8(14)

.877

.889

.941

D5,20E

.545

1.010

1.628

D5,22E

.693

1.010

1.009

D5,22Z

.719

1.017

.956

D5,24

.680

1.009

.937

D5,25

.681

1.009

.928

D6,8

.576

.793

.939

D6,8(14)

.893

.643

.942

D7,9(11)

.505

.902

.915

D7,14

.829

.788

.925

D7,24

.536

.797

.942

D8,14

.818

.991

.938

D8,24

.610

.951

.946

D5,7,9(11)

.566

1.246

.922

D5,7,9-19-nortriene

.588

.995

Vitamin D3

.543

.919

D5,22E,24

.709

1.012

1.045

D6,8,14

.817

.854

.955

Boldface indicates estimated values

 

 

C27 sterol acetates

Double bond

H-18

H-19

H-21

D0

.646

.816

.897*

D4

.676

1.061

.901*

D5 (cholesterol Ac)

.677

1.019

.914*

D6

.689

.794

.906*

D7

.533

.810

.919*

D8

.606

.963

.923*

D8(14)

.838

.704

.929*

D14

.898

.836

.910*

D4,6

.724

1.010

.910*

D5,7

.618

.953

.941*

D5,8

.650

1.200

.934*

D5,8(14)

.875

.899

.941*

D5,20E

.544

1.020

1.628*

D5,22E

.692

1.020

1.009*

D5,22Z

.720

1.027

.956*

D5,24

.678

1.019

.936*

D6,8

.573

.806

.939*

D6,8(14)

.892

.657

.941*

D7,9(11)

.503

.916

.915*

D7,14

.827

.801

.924*

D7,24

.533

.810

.941*

D8,14

.816

1.004

.938*

D8,24

.607

.963

.945*

D5,7,9(11)

.563

1.256

.922*

Vitamin D3 Ac

.540

.919*

D5,7,9-19-nortriene

.594

.997*

D5,22E,24

.706

1.021

1.045*

D6,8,14

.814

.867

.956*

 

 

Methyl resonances sorted in order of increasing chemical shift

C27 free sterols

 

Double bond

Chemical shift

D7,9(11)

.505

D7

.534

Vitamin D3

.543

D5,20E

.545

D5,7,9(11)

.566

D6,8

.576

D5,7,9-19-nortriene

.588

D8

.609

D8,24

.610

D5,7

.620

D6,8(14)

.643

D0

.647

D0

.647

D5,8

.652

D4

.677

D5

.678

D5,24

.680

D5,25

.681

D8(14)

.689

D6

.691

D5,22E,24

.709

D4,6

.725

D6

.780

D7,14

.788

D6,8

.793

D7

.796

D6,8,14

.817

D8,14

.818

D14

.822

D7,14

.829

D8(14)

.840

D6,8,14

.854

D5,8(14)

.877

D5,8(14)

.889

D6,8(14)

.893

D0

.897

D14

.899

D4

.900

D7,9(11)

.902

D6

.906

D4,6

.909

D14

.910

D5

.914

D7,9(11)

.915

Vitamin D3

.919

D7

.920

D5,7,9(11)

.922

D8

.923

D7,14

.925

D5,25

.928

D8(14)

.929

D5,8

.934

D5,24

.937

D8,14

.938

D6,8

.939

D5,7

.941

D5,8(14)

.941

D6,8(14)

.942

D5,7

.946

D8,24

.946

D8

.950

D8,24

.951

D6,8,14

.955

D8,14

.991

D5,7,9-19-nortriene

.995

D4,6

.997

D5

1.008

D5,24

1.009

D5,25

1.009

D5,20E

1.010

D5,22E,24

1.012

D5,22E,24

1.045

D4

1.048

D5,8

1.188

D5,7,9(11)

1.246

D5,20E

1.628

 

Methyl resonances sorted in order of increasing chemical shift

C27 sterol acetates

Double bond

Chemical shift

D7,9(11)

.503

D7

.533

D7,24

.533

Vitamin D3 Ac

.540

D5,7,9(11)

.563

D6,8

.573

D5,7,9-19-nortriene

.594

D8

.606

D8,24

.607

D5,7

.618

D0

.646

D5,8

.650

D6,8(14)

.657

D4

.676

D5

.677

D5,24

.678

D6

.689

D5,22E

.692

D8(14)

.704

D5,22Z

.720

D4,6

.724

D6

.794

D7,14

.801

D6,8

.806

D7

.810

D7,24

.810

D8,14

.816

D0

.816

D7,14

.827

D14

.836

D8(14)

.838

D6,8,14

.867

D6,8,14

.867

D5,8(14)

.875

D6,8(14)

.892

D0

.897*

D14

.898

D5,8(14)

.899

D4

.901*

D6

.906*

D14

.910*

D4,6

.910*

D5

.914*

D7,9(11)

.915*

D7,9(11)

.916

D7

.919*

Vitamin D3 Ac

.919*

D5,7,9(11)

.922*

D8

.923*

D7,14

.924*

D8(14)

.929*

D5,8

.934*

D5,24

.936*

D8,14

.938*

D6,8

.939*

D5,7

.941*

D5,8(14)

.941*

D6,8(14)

.941*

D7,24

.941*

D8,24

.945*

D5,7

.953

D5,22Z

.956*

D6,8,14

.956*

D8

.963

D8,24

.963

D5,7,9-19-nortriene

.997*

D8,14

1.004

D5,22E

1.009*

D4,6

1.010

D5

1.019

D5,24

1.019

D5,22E

1.020

D5,22E,24

1.021

D5,22E,24

1.021

D5,22Z

1.027

D5,22E,24

1.045*

D4

1.061

D5,8

1.200

D5,7,9(11)

1.256

Asterisk (*) indicates H-21 (shown for acetate data only)