1-Hexadecanol

1-Hexadecanol is a fatty alcohol used to make other chemicals.

1H NMR investigations of inclusion complexes between beta-cyclodextrin and 1-hexadecanol.[Pubmed:18045091]

Curr Drug Discov Technol. 2007 Dec;4(4):295-7.

The inclusion complex between beta-CD and 1-Hexadecanol is synthesized and identified via (1)H NMR spectrum. The possible conformation of the inclusion complex is figured out. Via MM2 calculations, the possibility of complexation is verified.

Metabolic engineering of Saccharomyces cerevisiae to improve 1-hexadecanol production.[Pubmed:25466225]

Metab Eng. 2015 Jan;27:10-19.

Fatty alcohols are important components of a vast array of surfactants, lubricants, detergents, pharmaceuticals and cosmetics. We have engineered Saccharomyces cerevisiae to produce 1-Hexadecanol by expressing a fatty acyl-CoA reductase (FAR) from barn owl (Tyto alba). In order to improve fatty alcohol production, we have manipulated both the structural genes and the regulatory genes in yeast lipid metabolism. The acetyl-CoA carboxylase gene (ACC1) was over-expressed, which improved 1-Hexadecanol production by 56% (from 45mg/L to 71mg/L). Knocking out the negative regulator of the INO1 gene in phospholipid metabolism, RPD3, further enhanced 1-Hexadecanol production by 98% (from 71mg/L to 140mg/L). The cytosolic acetyl-CoA supply was next engineered by expressing a heterologous ATP-dependent citrate lyase, which increased the production of 1-Hexadecanol by an additional 136% (from 140mg/L to 330mg/L). Through fed-batch fermentation using resting cells, over 1.1g/L 1-Hexadecanol can be produced in glucose minimal medium, which represents the highest titer reported in yeast to date.

Metabolic engineering of Saccharomyces cerevisiae to produce 1-hexadecanol from xylose.[Pubmed:26830023]

Microb Cell Fact. 2016 Feb 1;15:24.

BACKGROUND: An advantageous but challenging approach to overcome the limited supply of petroleum and relieve the greenhouse effect is to produce bulk chemicals from renewable materials. Fatty alcohols, with a billion-dollar global market, are important raw chemicals for detergents, emulsifiers, lubricants, and cosmetics production. Microbial production of fatty alcohols has been successfully achieved in several industrial microorganisms. However, most of the achievements were using glucose, an edible sugar, as the carbon source. To produce fatty alcohols in a renewable manner, non-edible sugars such as xylose will be a more appropriate feedstock. RESULTS: In this study, we aim to engineer a Saccharomyces cerevisiae strain that can efficiently convert xylose to fatty alcohols. To this end, we first introduced the fungal xylose utilization pathway consisting of xylose reductase (XR), xylitol dehydrogenase (XDH), and xylulose kinase (XKS) into a fatty alcohol-producing S. cerevisiae strain (XF3) that was developed in our previous studies to achieve 1-Hexadecanol production from xylose at 0.4 g/L. We next applied promoter engineering on the xylose utilization pathway to optimize the expression levels of XR, XDH, and XKS, and increased the 1-Hexadecanol titer by 171 %. To further improve the xylose-based fatty alcohol production, two optimized S. cerevisiae strains from promoter engineering were evolved with the xylose as the sole carbon source. We found that the cell growth rate was improved at the expense of decreased fatty alcohol production, which indicated 1-Hexadecanol was mainly produced as a non-growth associated product. Finally, through fed-batch fermentation, we successfully achieved 1-Hexadecanol production at over 1.2 g/L using xylose as the sole carbon source, which represents the highest titer of xylose-based 1-Hexadecanol reported in microbes to date. CONCLUSIONS: A fatty alcohol-producing S. cerevisiae strain was engineered in this study to produce 1-Hexadecanol from xylose. Although the xylose pathway we developed in this study could be further improved, this proof-of-concept study, for the first time to our best knowledge, demonstrated that the xylose-based fatty alcohol could be produced in S. cerevisiae with potential applications in developing consolidated bioprocessing for producing other fatty acid-derived chemicals.

Effects of dioctadecyl dimethyl ammonium chloride on the rheological behavior of behenyl trimethyl ammonium chloride/1-hexadecanol/water ternary system.[Pubmed:16839564]

J Colloid Interface Sci. 2006 Oct 1;302(1):341-6.

The effects of dioctadecyl dimethyl ammonium chloride (DODAC) on the rheological properties of ternary systems consisting of behenyl trimethyl ammonium chloride (C22TAC), 1-Hexadecanol (C16OH), and water are studied to improve the long-term stability and to establish the preparation method of cosmetic products. The basic ternary systems behave as solids at low stresses, due to the formation of lamella liquid crystals called alpha gel. The additions of DODAC to ternary systems cause the rupture of alpha gel structures and transformation to vesicles. The structures of molecular assemblies are confirmed through particle size distribution, differential scanning calorimetry, and freeze fracture electron microscopy. The vesicle structures formed in coexistence of single-chain surfactant and double-chain surfactant are highly stable. Because the quaternary systems are considered to be constructed by the mixtures of alpha gel and vesicles at the appropriate concentrations of DODAC, the rheology can be controlled by the structural balance between them.