:3,3-Dimethyl-1-butanol
{{one source|date=January 2016}}
{{Chembox
| ImageFile = 3,3-Dimethyl-1-butanol.svg
| ImageSize = 200px
| ImageAlt =
| PIN = 3,3-Dimethylbutan-1-ol
| OtherNames = 3,3-Dimethyl-1-butanol
| Section1 = {{Chembox Identifiers
| CASNo = 624-95-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 543OYD666T
| PubChem = 12233
| ChemSpiderID = 11732
| SMILES = CC(C)(C)CCO
| InChI = 1/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3
| InChIKey = DUXCSEISVMREAX-UHFFFAOYAW
| StdInChI = 1S/C6H14O/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3
| StdInChIKey = DUXCSEISVMREAX-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C = 6 | H = 14 | O = 1
| Appearance =
| Density = 0.844 g/cm3 (15 °C)
| MeltingPtC = -60
| BoilingPtC = 143
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
3,3-Dimethyl-1-butanol (DMB) is a structural analog of choline.{{cite journal|last1=Wang|first1=Zeneng|last2=Roberts|first2=Adam B.|last3=Buffa|first3=Jennifer A.|last4=Levison|first4=Bruce S.|last5=Zhu|first5=Weifei|last6=Org|first6=Elin|last7=Gu|first7=Xiaodong|last8=Huang|first8=Ying|last9=Zamanian-Daryoush|first9=Maryam|last10=Culley|first10=Miranda K.|last11=DiDonato|first11=Anthony J.|last12=Fu|first12=Xiaoming|last13=Hazen|first13=Jennie E.|last14=Krajcik|first14=Daniel|last15=DiDonato|first15=Joseph A.|last16=Lusis|first16=Aldons J.|last17=Hazen|first17=Stanley L.|title=Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis|journal=Cell|date=December 2015|volume=163|issue=7|pages=1585–1595|doi=10.1016/j.cell.2015.11.055|url= |pmid=26687352|pmc=4871610}}
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.{{Cite patent|number=EP0081050A1|title=Process for the production of pure neohexanol|gdate=1983-06-15|invent1=Kaufhold|inventor1-first=Manfred Dr|url=https://patents.google.com/patent/EP0081050/en}}
Occurrence
DMB is found in some balsamic vinegars, red wines, and some cold-pressed extra virgin olive oils and grape seed oils.