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3,3-Dimethyl-1-butanol

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3,3-Dimethyl-1-butanol
Names
Preferred IUPAC name 3,3-Dimethylbutan-1-ol
Other names 3,3-Dimethyl-1-butanol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.884 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3Key: DUXCSEISVMREAX-UHFFFAOYSA-N
  • InChI=1/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3Key: DUXCSEISVMREAX-UHFFFAOYAW
SMILES
  • CC(C)(C)CCO
Properties
Chemical formula C6H14O
Molar mass 102.177 g·mol
Density 0.844 g/cm @ Temp: 15 °C
Melting point -60 °C
Boiling point 143 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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. It consequently inhibited choline-enhanced endogenous macrophage foam cell formation and atherosclerotic lesion development in mice without alterations in circulating cholesterol levels.

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.

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

Occurrence

DMB is found in some balsamic vinegars, red wines, and some cold-pressed extra virgin olive oils and grape seed oils.

References

  1. ^ 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 
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