Isoprenoid

DATA No : IIP0028 INFORMANT : Hiroshi Sagami

NAME : [2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-ol

COMMON NAME	:	Undecaprenol, wt3c7-C55-prenol, Prenol-11
SYMBOL	:
FORMULA	:	C₅₅H₉₀O MOL.WT (average) : 767.303

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

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SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	1H-NMR spectrum at 100MHz (with spectrum)(Ref. 0021). The head and tail sites of undecaprenol exibit a fast motion as exibited in the short chain isoprenols. Undecaprenol appears to induce a non-bilayer (isotropic) organization of phospholipid molecules in PE/PC (2:1) vesicles.(Ref. 0085)

MASS SPECTRA	:	(with spectrum)(Ref. 0021)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

The compound was isolated from silkworm feces.(Ref. 0003) Plant(Ref. 0021).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. Dolichol and dolichol derivatives destabilize unsaturated phosphatidylethanolamine containing bilayer structures and promote hexagonal II phase formation. Dolichol and dolichyl-P increase the fatty acid fluidity in phosphatidylethanolamine mixtures(Ref. 0044).

REFERENCES

[0003]

AUTHOR	:	Fukawa,H., Toyoda, M., Shimizu, T.,and Murohashi, M.
TITLE	:	Isolation of new isoprenyl alcohols from silkworm feces
JOURNAL	:	Tetrahedron Lett.
VOL	:	49 PAGE : 6209 -6213 (1966)

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[0021]

AUTHOR	:	Mankowski, T., Jankowski, W., Chojnacki, T., and Franke, P.
TITLE	:	C55-Dolichol: occurrence in pig liver and preparation by hydrogenation of plant undecaprenol PubMed ID:1276128
JOURNAL	:	Biochemistry.
VOL	:	15 PAGE : 2125-2130 (1976)

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[0044]

AUTHOR	:	Valtersson, C., van Duyn, G., Verkleij, A. J., Chojnacki, T., de Kruijff, B., and Dallner, G.
TITLE	:	The influence of dolichol, dolichol esters, and dolichyl phosphate on phospholipid polymorphism and fluidity in model membranes PubMed ID:3919007
JOURNAL	:	J Biol Chem.
VOL	:	260 PAGE : 2742-2751 (1985)

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[0085]

AUTHOR	:	Knudsen, M. J., and Troy, F. A.
TITLE	:	Nuclear magnetic resonance studies of polyisoprenols in model membranes PubMed ID:2611961
JOURNAL	:	Chem Phys Lipids.
VOL	:	51 PAGE : 205-212 (1989)

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