3,3-Dimethyl-1-butanol

Last updated
3,3-Dimethyl-1-butanol
3,3-Dimethyl-1-butanol.svg
Names
Preferred IUPAC name
3,3-Dimethylbutan-1-ol
Other names
3,3-Dimethyl-1-butanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.884 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3
    Key: DUXCSEISVMREAX-UHFFFAOYSA-N
  • InChI=1/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3
    Key: DUXCSEISVMREAX-UHFFFAOYAW
  • CC(C)(C)CCO
Properties
C6H14O
Molar mass 102.177 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,3-Dimethyl-1-butanol (DMB) is a structural analog of choline. [1]

Contents

Effects

DMB inhibits microbial trimethylamine (TMA) formation in mice and in human feces, thereby reducing plasma trimethylamine N-oxide (TMAO) levels after choline or carnitine supplementation. [1] It consequently inhibited choline-enhanced endogenous macrophage foam cell formation and atherosclerotic lesion development in mice without alterations in circulating cholesterol levels. [1]

While mice placed on a choline supplemented diet showed an increase in the proportions of the bacterial taxon Clostridiales in the gut, DMB induced a decrease in the proportions of this taxon. [1]

Mice showed no evidence of toxicity to chronic (16-week) DMB exposure. [1] [2]

Occurrence

DMB is found in some balsamic vinegars, red wines, and some cold-pressed extra virgin olive oils and rapeseed oils. [1]

Related Research Articles

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Choline is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.

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<span class="mw-page-title-main">Bacillota</span> Phylum of bacteria

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<span class="mw-page-title-main">Butyric acid</span> Chemical compound

Butyric acid, also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.

<i>Lactobacillus acidophilus</i> Species of bacterium

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<span class="mw-page-title-main">Trimethylamine</span> Chemical compound responsible for rotten fish odor

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<span class="mw-page-title-main">Trimethylaminuria</span> Medical condition

Trimethylaminuria (TMAU), also known as fish odor syndrome or fish malodor syndrome, is a rare metabolic disorder that causes a defect in the normal production of an enzyme named flavin-containing monooxygenase 3 (FMO3). When FMO3 is not working correctly or if not enough enzyme is produced, the body loses the ability to properly convert the fishy-smelling chemical trimethylamine (TMA) from precursor compounds in food digestion into trimethylamine oxide (TMAO), through a process called N-oxidation.

<span class="mw-page-title-main">Trimethylglycine</span> Chemical compound

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<span class="mw-page-title-main">Free fatty acid receptor 2</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">TAAR5</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">Microbiota</span> Community of microorganisms

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Skin immunity is a property of skin that allows it to resist infections from pathogens. In addition to providing a passive physical barrier against infection, the skin also contains elements of the innate and adaptive immune systems which allows it to actively fight infections. Hence the skin provides defense in depth against infection.

<span class="mw-page-title-main">Microbiome</span> Microbial community assemblage and activity

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Emily P. Balskus is an American chemical biologist, enzymologist, microbiologist, and biochemist born in Cincinnati, Ohio in 1980. She has been on the faculty of the Chemistry and Chemical Biology department of Harvard University since 2011 and is currently the Morris Kahn Professor. She has published more than 80 peer-reviewed papers and three book chapters. Since 2012 she has been invited to give over 170 lectures, has held positions on various editorial boards, and served as a reviewer for ACS and Nature journals among others. Balskus also currently serves as a consultant for Novartis, Kintai Therapeutics, and Merck & Co.

References

  1. 1 2 3 4 5 6 Wang, Zeneng; Roberts, Adam B.; Buffa, Jennifer A.; Levison, Bruce S.; Zhu, Weifei; Org, Elin; Gu, Xiaodong; Huang, Ying; Zamanian-Daryoush, Maryam; Culley, Miranda K.; DiDonato, Anthony J.; Fu, Xiaoming; Hazen, Jennie E.; Krajcik, Daniel; DiDonato, Joseph A.; Lusis, Aldons J.; Hazen, Stanley L. (December 2015). "Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis". Cell. 163 (7): 1585–1595. doi:10.1016/j.cell.2015.11.055. PMC   4871610 . PMID   26687352.
  2. EP0081050A1,Kaufhold, Manfred Dr,"Process for the production of pure neohexanol",issued 1983-06-15