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Chemical Compound Review

Cetaffine     hexadecan-1-ol

Synonyms: Cetanol, Cetylol, Hyfatol, Cetal, Ethal, ...
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Disease relevance of SSD

  • Gas-phase pyrolysis of 1-hexadecanol results in a series of monounsaturated alcohols and alpha-olefins analogous to fragmentation found for methyl palmitate, as well as an additional peak corresponding to the pyrolytic dehydration product, 1-hexadecene [1].
  • Growth of Acinetobacter sp. strain HO1-N on n-hexadecanol: physiological and ultrastructural characteristics [2].
  • Farnesol, tetradecanol, hexadecanol, and hexadecenol all were significantly enriched in (13)C compared to bulk dissolved and particulate organic carbon and compared to the biomarkers of purple sulfur bacteria [3].
  • HPC was more cytotoxic (IC50, 37 microM) than its phosphate metabolite (IC50, 140 microM), but its toxicity was similar to that of its metabolite hexadecanol (IC50, 28 microM), suggesting that only the former metabolic route leads to detoxification [4].
  • Sequence analysis of the V3 region of HIV-1 isolates indicated that patients with high-affinity/avidity antibodies to PNDMN and PNDSC had a PND with an internal 12-amino acid sequence (serotype-specific domain, SSD) that was highly homologous (> 90%) with the MN and SC SSD [5].

Psychiatry related information on SSD

  • Patients were divided on the basis of intake MDE recovery into residual depressive symptoms (SSD; N=82) and asymptomatic (N=155) recovery groups [6].

High impact information on SSD

  • The hexadecanol content of SLS fibroblasts was abnormally elevated [7].
  • SSD is essential for protein translocation, is unique to SecA, and is absent from other DEAD proteins [8].
  • Binding is abrogated by deletion of residues 219-244 that lie within SSD, a novel substrate specificity element of the ATPase subdomain [8].
  • In the accompanying paper (James, P. F., and Zoeller, R. A. (1997) J. Biol. Chem. 272, 23532-23539), we reported the isolation of a series of mutants from the fibroblast-like cell line, CHO-K1, that are deficient in the incorporation of the long chain fatty alcohol, hexadecanol, into complex lipids [9].
  • When the mutant SSD cells are fed [3H]acetate, radioactivity accumulates in farnesol, much of which is secreted into the medium [10].

Chemical compound and disease context of SSD


Biological context of SSD

  • In lipid-poor medium, SSD cell growth is arrested [10].
  • In every assay performed the revertant SSR cells exhibited a phenotype that was essentially wild type, demonstrating that the SSD mutant phenotype was the result of a single mutation [10].
  • Consistent with the composition of the meibomian gland secretion, exogenous acyl-CoA longer than C14 and shorter than C20 gave maximal rates of esterification of hexadecanol [15].
  • Tetradecanol and hexadecanol are not anesthetic to tadpoles, but they did expand the membrane [16].
  • The threshold for detection of displacements of visual objects is higher during voluntary saccades than it is during steady gaze ("saccadic suppression of displacement"; SSD) [17].

Anatomical context of SSD


Associations of SSD with other chemical compounds


Gene context of SSD

  • We studied the binding and effect of a series of n-alkanols up to hexadecanol (C16) on two model proteins, BSA and myoglobin (MGB), using hydrogen-tritium exchange and light scattering [27].
  • Our method explicitly accounts for MLC-specific effects (spectral hardening, tongue-and-groove, head scatter) as well as changes in SSD with isocentric displacement, assuming that the body moves rigidly with the isocenter [28].
  • The calculation shows that the effect of SSD on PSF for high energy photon beams is not significant for small fields, but can be as high as 1% for large fields [29].
  • The RPC has measured both TPR20/TPR10 and the corresponding ratio of percent depth dose (D20/D10) at a constant SSD for 685 photon beams (4-25 MV) for most makes and models if accelerators [30].
  • The Br. thermoruber Lon gene (Bt-lon) encodes an 88 kDa protein characterized by an N-terminal domain, a central ATPase domain which includes an SSD (sensor- and substrate-discrimination) domain, and a C-terminal protease domain [31].

Analytical, diagnostic and therapeutic context of SSD

  • It is argued that %dd(10), the percentage depth dose at 10 cm in a 10 x 10 cm2 photon beam at a SSD of 100 cm, is a better beam quality specifier for radiotherapy beams than the commonly used values of TPR10(20) or nominal accelerating potential (NAP) [32].
  • METHODS: The studies were performed using the SSD 2000 Multiview Ultrasound Scanner and the UST 5536 7.0-MHz laparoscopic transducer probe [33].
  • The properties of Infasurf, a replacement lung surfactant derived from calf lung lavage organic extract, can be modified in a controlled fashion by adding hexadecanol (HD) [34].
  • Langmuir monolayers of mixtures of straight-chain and branched molecules of hexadecanol and eicosanol were studied using surface pressure-area isotherms, Brewster angle microscopy, and interfacial rheology measurements [35].
  • In athymic mice, half-body irradiation was performed in an AECL Cobalt unit, at an SSD of 80 cm [36].


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  2. Growth of Acinetobacter sp. strain HO1-N on n-hexadecanol: physiological and ultrastructural characteristics. Singer, M.E., Tyler, S.M., Finnerty, W.R. J. Bacteriol. (1985) [Pubmed]
  3. Characterization and in situ carbon metabolism of phototrophic consortia. Glaeser, J., Overmann, J. Appl. Environ. Microbiol. (2003) [Pubmed]
  4. Is metabolism an important arbiter of anticancer activity of ether lipids? Metabolism of SRI 62-834 and hexadecylphosphocholine by [31P]-NMR spectroscopy and comparison of their cytotoxicities with those of their metabolites. Bishop, F.E., Dive, C., Freeman, S., Gescher, A. Cancer Chemother. Pharmacol. (1992) [Pubmed]
  5. Pattern of antibody response against the V3 loop in children with vertically acquired immunodeficiency virus type 1 (HIV-1) infection. De Rossi, A., Zanotto, C., Mammano, F., Ometto, L., Del Mistro, A., Chieco-Bianchi, L. AIDS Res. Hum. Retroviruses (1993) [Pubmed]
  6. Major depressive disorder: a prospective study of residual subthreshold depressive symptoms as predictor of rapid relapse. Judd, L.L., Akiskal, H.S., Maser, J.D., Zeller, P.J., Endicott, J., Coryell, W., Paulus, M.P., Kunovac, J.L., Leon, A.C., Mueller, T.I., Rice, J.A., Keller, M.B. Journal of affective disorders. (1998) [Pubmed]
  7. Sjögren-Larsson syndrome. Impaired fatty alcohol oxidation in cultured fibroblasts due to deficient fatty alcohol:nicotinamide adenine dinucleotide oxidoreductase activity. Rizzo, W.B., Dammann, A.L., Craft, D.A. J. Clin. Invest. (1988) [Pubmed]
  8. Allosteric communication between signal peptides and the SecA protein DEAD motor ATPase domain. Baud, C., Karamanou, S., Sianidis, G., Vrontou, E., Politou, A.S., Economou, A. J. Biol. Chem. (2002) [Pubmed]
  9. An animal cell mutant with a deficiency in acyl/alkyl-dihydroxyacetone-phosphate reductase activity. Effects on the biosynthesis of ether-linked and diacyl glycerolipids. James, P.F., Lake, A.C., Hajra, A.K., Larkins, L.K., Robinson, M., Buchanan, F.G., Zoeller, R.A. J. Biol. Chem. (1997) [Pubmed]
  10. Squalene synthase-deficient mutant of Chinese hamster ovary cells. Bradfute, D.L., Silva, C.J., Simoni, R.D. J. Biol. Chem. (1992) [Pubmed]
  11. Fatty aldehyde dehydrogenases in Acinetobacter sp. strain HO1-N: role in hexadecanol metabolism. Singer, M.E., Finnerty, W.R. J. Bacteriol. (1985) [Pubmed]
  12. Photoallergic and allergic reaction to 2-hydroxy-4-methoxybenzophenone (sunscreen) and allergy to cetyl alcohol in cosmetic cream. Kiec-Swierczynska, M., Krecisz, B., Swierczynska-Machura, D. Contact Derm. (2005) [Pubmed]
  13. Contact allergy in 330 dermatological patients. Blondeel, A., Oleffe, J., Achten, G. Contact Derm. (1978) [Pubmed]
  14. Evaluating skin-protective materials against contact irritants and allergens. An in vivo screening human model. Zhai, H., Willard, P., Maibach, H.I. Contact Derm. (1998) [Pubmed]
  15. Acyl-CoA reductase and acyl-CoA: fatty alcohol acyl transferase in the microsomal preparation from the bovine meibomian gland. Kolattukudy, P.E., Rogers, L. J. Lipid Res. (1986) [Pubmed]
  16. Erythrocyte membrane expansion due to the volatile anesthetics, the 1-alkanols, and benzyl alcohol. Bull, M.H., Brailsford, J.D., Bull, B.S. Anesthesiology (1982) [Pubmed]
  17. Saccadic suppression of displacement: separate influences of saccade size and of target retinal eccentricity. Li, W., Matin, L. Vision Res. (1997) [Pubmed]
  18. Sjögren-Larsson syndrome: inherited defect in the fatty alcohol cycle. Rizzo, W.B., Dammann, A.L., Craft, D.A., Black, S.H., Tilton, A.H., Africk, D., Chaves-Carballo, E., Holmgren, G., Jagell, S. J. Pediatr. (1989) [Pubmed]
  19. The dihydroxyacetonephosphate pathway for biosynthesis of ether lipids in Leishmania mexicana promastigotes. Heise, N., Opperdoes, F.R. Mol. Biochem. Parasitol. (1997) [Pubmed]
  20. Some properties of a hexadecane hydroxylation system in rabbit intestinal mucosa microsomes. Ichihara, K., Ishihara, K., Kusunose, E., Kusunose, M. J. Biochem. (1981) [Pubmed]
  21. Incorporation of [hydrogen-3] alkylglycerolether and [carbon-14] hexadecanol into bovine colostrum and milk lipids. Ahrné, L., Palmquist, D.L. J. Dairy Sci. (1982) [Pubmed]
  22. Radiation protection of the patient during radiotherapy. Novotny, J., Tarakanath, M.S. Strahlentherapie. (1976) [Pubmed]
  23. Alkyldihydroxyacetone-P synthase. Solubilization, partial purification, new assay method, and evidence for a ping-pong mechanism. Brown, A.J., Snyder, F. J. Biol. Chem. (1982) [Pubmed]
  24. Sjögren-Larsson syndrome: accumulation of free fatty alcohols in cultured fibroblasts and plasma. Rizzo, W.B., Craft, D.A. J. Lipid Res. (2000) [Pubmed]
  25. Modification of a standard cobalt-60 unit for total body irradiation at 150 cm SSD. Peters, V.G., Herer, A.S. Int. J. Radiat. Oncol. Biol. Phys. (1984) [Pubmed]
  26. Alcohol dehydrogenases in Acinetobacter sp. strain HO1-N: role in hexadecane and hexadecanol metabolism. Singer, M.E., Finnerty, W.R. J. Bacteriol. (1985) [Pubmed]
  27. Steric hindrance is not required for n-alkanol cutoff in soluble proteins. Eckenhoff, R.G., Tanner, J.W., Johansson, J.S. Mol. Pharmacol. (1999) [Pubmed]
  28. A stochastic convolution/superposition method with isocenter sampling to evaluate intrafraction motion effects in IMRT. Naqvi, S.A., D'Souza, W.D. Medical physics. (2005) [Pubmed]
  29. Peak scatter factors for high energy photon beams. Li, X.A. Medical physics. (1999) [Pubmed]
  30. An empirical relationship for determining photon beam quality in TG-21 from a ratio of percent depth doses. Followill, D.S., Tailor, R.C., Tello, V.M., Hanson, W.F. Medical physics. (1998) [Pubmed]
  31. Identification of a gene encoding Lon protease from Brevibacillus thermoruber WR-249 and biochemical characterization of its thermostable recombinant enzyme. Lee, A.Y., Tsay, S.S., Chen, M.Y., Wu, S.H. Eur. J. Biochem. (2004) [Pubmed]
  32. Beam quality specification for photon beam dosimetry. Kosunen, A., Rogers, D.W. Medical physics. (1993) [Pubmed]
  33. Laparoscopic insufflation of the abdomen reduces portal venous flow. Jakimowicz, J., Stultiëns, G., Smulders, F. Surgical endoscopy. (1998) [Pubmed]
  34. Modifying calf lung surfactant by hexadecanol. Alonso, C., Bringezu, F., Brezesinski, G., Waring, A.J., Zasadzinski, J.A. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  35. Interfacial rheology and structure of straight-chain and branched fatty alcohol mixtures. Kurtz, R.E., Lange, A., Fuller, G.G. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
  36. In vivo radiosensitizing effect of the adenovirus E1A gene in murine and human malignant tumors. Martin-Duque, P., Sánchez-Prieto, R., Romero, J., Martinez-Lamparero, A., Cebrian-Sagarriga, S., Guinea-Viniegra, J., Dominguez, C., Lleonart, M., Cano, A., Quintanilla, M., Ramón Y Cajal, S. Int. J. Oncol. (1999) [Pubmed]
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