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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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Hyperosmolar Hyperglycemic State01:21

Hyperosmolar Hyperglycemic State

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Hyperosmolar Hyperglycemic State, or HHS, is a serious and life-threatening complication of type 2 diabetes mellitus. It is characterized by three main features: severe hyperglycemia, profound dehydration, and elevated serum osmolality, all occurring without significant ketoacidosis.HHS typically develops in older adults or individuals with limited access to fluids. This may result from illness, cognitive impairment, or medications such as diuretics or corticosteroids. These factors reduce...
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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Related Experiment Video

Updated: Apr 24, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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β-hydroxybutyrate: much more than a metabolite.

John C Newman1, Eric Verdin2

  • 1Division of Geriatrics, University of California San Francisco, San Francisco, CA, USA; Gladstone Institutes, University of California San Francisco, 1650 Owens St., San Francisco, CA 94158, USA.

Diabetes Research and Clinical Practice
|September 7, 2014
PubMed
Summary

Beta-hydroxybutyrate (βOHB) is an energy source and a signaling molecule. It regulates cellular functions and gene expression, impacting metabolic diseases like type 2 diabetes.

Keywords:
AcetylationEpigeneticsHDACKetone bodiesLow carbohydrate

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Determining Basal Energy Expenditure and the Capacity of Thermogenic Adipocytes to Expend Energy in Obese Mice
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Isolating Brown Adipocytes from Murine Interscapular Brown Adipose Tissue for Gene and Protein Expression Analysis
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Determining Basal Energy Expenditure and the Capacity of Thermogenic Adipocytes to Expend Energy in Obese Mice
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Isolating Brown Adipocytes from Murine Interscapular Brown Adipose Tissue for Gene and Protein Expression Analysis
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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Metabolic Disease Research

Background:

  • Ketone body beta-hydroxybutyrate (βOHB) serves as an energy carrier during fasting and exercise.
  • Beyond energy, βOHB possesses critical cellular signaling functions.
  • βOHB's signaling roles link environmental cues to cellular activity and gene expression.

Purpose of the Study:

  • To elucidate the multifaceted roles of beta-hydroxybutyrate (βOHB) beyond its metabolic functions.
  • To explore βOHB's signaling pathways, including its interactions with HDACs and cell surface receptors.
  • To understand the implications of βOHB's regulatory functions in metabolic diseases such as type 2 diabetes.

Main Methods:

  • Investigated βOHB as an endogenous inhibitor of histone deacetylases (HDACs).
  • Examined βOHB's function as a ligand for cell surface receptors.
  • Analyzed the signaling activities of βOHB's downstream metabolic products (acetyl-CoA, succinyl-CoA, NAD+).

Main Results:

  • βOHB acts as an endogenous inhibitor of histone deacetylases (HDACs).
  • βOHB functions as a ligand for at least two cell surface receptors.
  • Metabolic products of βOHB, including acetyl-CoA, succinyl-CoA, and NAD+, exhibit signaling activities.

Conclusions:

  • βOHB is a key signaling molecule with diverse cellular regulatory functions.
  • These regulatory roles of βOHB are crucial for connecting the environment to cellular function and gene expression.
  • Understanding βOHB's signaling is vital for the pathogenesis and therapeutic strategies for metabolic diseases like type 2 diabetes.