Names | |||
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Preferred IUPAC name Butane-1,3-diol | |||
Other names 1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane | |||
Identifiers | |||
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3D model (JSmol) | |||
1731276 1718944 (R) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.003.209 | ||
EC Number |
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E number | E1502 (additional chemicals) | ||
2409 2493173 (R) | |||
KEGG | |||
MeSH | 1,3-Butylene+glycol | ||
PubChem CID | |||
RTECS number |
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UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C4H10O2 | |||
Molar mass | 90.122 g·mol−1 | ||
Appearance | Colourless liquid | ||
Density | 1.0053 g cm−3 | ||
Melting point | −50 °C (−58 °F; 223 K) | ||
Boiling point | 204 to 210 °C; 399 to 410 °F; 477 to 483 K | ||
1 kg dm−3 | |||
log P | −0.74 | ||
Vapor pressure | 8 Pa (at 20 °C) | ||
Refractive index (nD) | 1.44 | ||
Thermochemistry | |||
Std molar entropy (S⦵298) | 227.2 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −501 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −2.5022 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Warning | |||
H319, H413 | |||
P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
Flash point | 108 °C (226 °F; 381 K) | ||
394 °C (741 °F; 667 K) | |||
Related compounds | |||
Related butanediol | 1,2-Butanediol | ||
Related compounds | 2-Methylpentane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol. [1] [2] [3] It is used in flavoring, [4] and as a precursor to some antibiotics. [5]
Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol: [6]
Dehydration of 1,3-butanediol gives 1,3-butadiene:
1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R) enantiomer being more active. [7] [8] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis. [9] [10] [11] [12] [13] [14]
1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper ( Capsicum annuum ), red bell peppers, and yellow bell peppers. [15] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule. [16]
In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
Succinic acid is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.
In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.
Polyvinyl alcohol (PVOH, PVA, or PVAl) is a water-soluble synthetic polymer. It has the idealized formula [CH2CH(OH)]n. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) adhesive formulations, in a variety of coatings, and 3D printing. It is colourless (white) and odorless. It is commonly supplied as beads or as solutions in water. Without an externally added crosslinking agent, PVA solution can be gelled through repeated freezing-thawing, yielding highly strong, ultrapure, biocompatible hydrogels which have been used for a variety of applications such as vascular stents, cartilages, contact lenses, etc.
In organic chemistry, enols are a type of Functional group or intermediate in organic chemistry with the formula R2C=CROH. The term enol is an abbreviation of alkenol, a portmanteaus deriving from "-ene"/"alkene" and the "-ol". Many kinds of enols are known.
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.
Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran (THF) by replacement of the methylene group (CH2) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a peroxide. 1,3-dioxolane is used as a solvent and as a comonomer in polyacetals.
In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing C−PO(OR)2 groups, where R is an organic group. If R is hydrogen then the compound is a dialkyl phosphite, which is a different functional group. Phosphonic acids, typically handled as salts, are generally nonvolatile solids that are poorly soluble in organic solvents, but soluble in water and common alcohols.
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.
β-Hydroxybutyric acid, also known as 3-hydroxybutyric acid or BHB, is an organic compound and a beta hydroxy acid with the chemical formula CH3CH(OH)CH2CO2H; its conjugate base is β-hydroxybutyrate, also known as 3-hydroxybutyrate. β-Hydroxybutyric acid is a chiral compound with two enantiomers: D-β-hydroxybutyric acid and L-β-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature. In humans, D-β-hydroxybutyric acid is one of two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor (GPCR).
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.
2,3-Butanediol is the organic compound with the formula (CH3CHOH)2. It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.
In organic chemistry, 3-hydroxybutanal is an organic compound with the formula CH3CH(OH)CH2CHO and the structure H3C−CH(OH)−CH2−CH=O. It is classified as an aldol and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of the dimerization of acetaldehyde. A thick colorless or pale-yellow liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.
Neopentyl glycol is an organic chemical compound. It is used in the synthesis of polyesters, paints, lubricants, and plasticizers. When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water. By esterification reaction with fatty or carboxylic acids, synthetic lubricating esters with reduced potential for oxidation or hydrolysis, compared to natural esters, can be produced.
2-Methyl-2,4-pentanediol (MPD) is an organic compound with the formula (CH3)2C(OH)CH2CH(OH)CH3. This colourless liquid is a chiral diol. It is produced industrially from diacetone alcohol by hydrogenation. Total European and USA production was 15000 tonnes in 2000.
Brianna Stubbs is an elite British rower and research scientist who won two gold medals for Great Britain at the 2013 U23 and 2016 World Rowing Championships. She was the youngest person to row across the English Channel when she completed the feat in 2004, at the age of 12. Her research is focussed on the metabolism of ketone drinks, and has been based at Oxford University. In 2014, she was included in the BBC's 100 Women.
Exogenous ketones are a class of ketone bodies that are ingested using nutritional supplements or foods. This class of ketone bodies refers to the three water-soluble ketones. These ketone bodies are produced by interactions between macronutrient availability such as low glucose and high free fatty acids or hormone signaling such as low insulin and high glucagon/cortisol. Under physiological conditions, ketone concentrations can increase due to starvation, ketogenic diets, or prolonged exercise, leading to ketosis. However, with the introduction of exogenous ketone supplements, it is possible to provide a user with an instant supply of ketones even if the body is not within a state of ketosis before ingestion. However, drinking exogenous ketones will not trigger fat burning like a ketogenic diet.