3,3-Dimethyl-1-butanol

3,3-Dimethyl-1-butanol
Names
	Preferred IUPAC name 3,3-Dimethylbutan-1-ol
	Other names 3,3-Dimethyl-1-butanol
Identifiers
CAS Number	624-95-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	11732;
ECHA InfoCard	100.009.884
PubChem CID	12233;
UNII	543OYD666T ;
CompTox Dashboard (EPA)	DTXSID3060796 ;
	InChI 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;
	SMILES CC(C)(C)CCO;
Properties
Chemical formula	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). Infobox references

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

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]

Occurrence

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

References

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.

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[cell.2015.11.055-1] 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.