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
Density	0.844 g/cm3 @ 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 [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]^[2]

Occurrence

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

References

^ ^a ^b ^c ^d ^e ^f 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.
^ EP0081050A1, Kaufhold, Manfred Dr, "Process for the production of pure neohexanol", issued 1983-06-15

[cell.2015.11.055-1] ^ ^a ^b ^c ^d ^e ^f 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

[1]

[2]