1,3-Butanediol

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1,3-Butanediol
Skeletal formula of 1,3-butanediol 1,3-Butanediol.png
Skeletal formula of 1,3-butanediol
Ball and stick model of 1,3-butanediol (S) 1,3-Butanediol-3D-balls.png
Ball and stick model of 1,3-butanediol (S)
Spacefill model of 1,3-butanediol (S) 1,3-Butanediol-3D-spacefill.png
Spacefill model of 1,3-butanediol (S)
Names
Preferred IUPAC name
Butane-1,3-diol
Other names
1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane
Identifiers
3D model (JSmol)
1731276

1718944 (R)
1718943 (S)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.209 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
PubChem CID
RTECS number
  • EK0440000
UNII
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 X mark.svgN
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N X mark.svgN
  • CC(O)CCO
Properties
C4H10O2
Molar mass 90.122 g·mol−1
AppearanceColourless 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)
1.44
Thermochemistry
Std molar
entropy
(S298)
227.2 J K−1 mol−1
−501 kJ mol−1
−2.5022 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319, H413
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 108 °C (226 °F; 381 K)
394 °C (741 °F; 667 K)
Related compounds
Related butanediol
1,2-Butanediol

1,4-Butanediol
2,3-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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH, not to be confused with 1,4 Butanediol. With two alcohol functional groups, the molecule is classified as a diol. The compound without the R (or D) designation is racemic, which is what has been used in most studies before 2023. 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 grape flavoring, [4] and as a precursor to some antibiotics. [5]

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol: [6]

CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH

Dehydration of 1,3-butanediol gives 1,3-butadiene:

CH3CH(OH)CH2CH2OH → CH2=CH-CH=CH2 + 2 H2O

Pharmacology

1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R), also known as (D), enantiomer being more active. [7] [8] Fatty acid esters of 1,3-butanediol such as the acetoacetate, lactate or hexanoate have been researched for inducing ketogenesis. [9] [10] [11] [12] [13] [14] [15]

Occurrence

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper ( Capsicum annuum ), red bell peppers, and yellow bell peppers. [16] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule. [17]

Related Research Articles

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In chemistry, an alcohol, is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Propylene glycol</span> Chemical compound

Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.

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Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

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.

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<span class="mw-page-title-main">Phosphonate</span> Organic compound containing C–PO(OR)2 groups

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β-Hydroxybutyric acid Chemical compound

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).

Free fatty acid receptors (FFARs) are G-protein coupled receptors (GPRs). GPRs are a large family of receptors. They reside on their parent cells' surface membranes, bind any one of a specific set of ligands that they recognize, and thereby are activated to elicit certain types of responses in their parent cells. Humans express more than 800 different types of GPCRs. FFARs are GPCR that bind and thereby become activated by particular fatty acids. In general, these binding/activating fatty acids are straight-chain fatty acids consisting of a carboxylic acid residue, i.e., -COOH, attached to aliphatic chains, i.e. carbon atom chains of varying lengths with each carbon being bound to 1, 2 or 3 hydrogens. For example, propionic acid is a short-chain fatty acid consisting of 3 carbons (C's), CH3-CH2-COOH, and docosahexaenoic acid is a very long-chain polyunsaturated fatty acid consisting of 22 C's and six double bonds : CH3-CH2-CH1=CH1-CH2-CH1=CH1-CH2-CH1=CH1-CH2-CH1=CH1-CH2-CH1=CH1-CH2-CH1=CH1-CH2-CH2-COOH.

<span class="mw-page-title-main">(R,R)-butanediol dehydrogenase</span> Class of enzymes

In enzymology, a (R,R)-butanediol dehydrogenase (EC 1.1.1.4) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">2,3-Butanediol</span> Chemical compound

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.

<span class="mw-page-title-main">Neopentyl glycol</span> Chemical compound

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<span class="mw-page-title-main">2-Methyl-2,4-pentanediol</span> Chemical compound

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Exogenous ketones are a class of ketone bodies that are ingested using nutritional supplements or foods. This class of ketone bodies refers mainly to β-hydroxybutyrate [BHB]. The body can make BHB endogenously, via the liver, 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.

<span class="mw-page-title-main">2-Methyl-2-propyl-1,3-propanediol</span> Chemical compound

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References

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