3-Hydroxypropionic acid

Last updated
3-Hydroxypropionic acid [1]
3-Hydroxypropionic-acid-2D-skeletal.svg
3-hydroxypropionic-acid-3D-balls.png
Names
Preferred IUPAC name
3-Hydroxypropanoic acid
Other names
3-Hydroxypropionic acid
Hydracrylic acid
Ethylene lactic acid
Identifiers
3D model (JSmol)
3DMet
773806
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.250 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-974-8
KEGG
PubChem CID
UNII
  • InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) Yes check.svgY
    Key: ALRHLSYJTWAHJZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
    Key: ALRHLSYJTWAHJZ-UHFFFAOYAU
  • O=C(O)CCO
Properties
C3H6O3
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Very soluble
Acidity (pKa)4.87 [2]
Related compounds
acetic acid
glycolic acid
propionic acid
lactic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds
1-propanol
2-propanol
propionaldehyde
acrolein
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.9. [2] It is very soluble in water, soluble in ethanol and diethyl ether. Upon distillation, it dehydrates to form acrylic acid, and is occasionally called hydracrylic acid

Contents

3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates.

Synthesis

3-Hydroxypropionic acid can be obtained by base-induced hydration of acrylic acid followed by reacidification. Another synthesis involves cyanation of ethylene chlorohydrin followed by hydrolysis of the resulting nitrile. Hydrolysis of propiolactone is yet another route. [3] Propiolactone, the dehydrated derivative of 3-hydroxypropionic acid, is produced by reaction of ketene and formaldehyde. [4]

3-Hydroxypropionic acid is listed as one of the "top" chemicals that could be produced from renewable resources. In particular, it could be produced by manipulation of glycerol, but this technology has not reached a commercial stage. [5] It can also be produced from glucose via pyruvate and malonyl coenzyme A. [4] [6]

Potential applications

3-Hydroxypropionic acid is of interest as a bio-derived precursor to acrylic acid. [5]

The polyester poly(3-hydroxypropionic acid) is a biodegradable polymer. [7] The method combines the high-molecular weight and control aspects of ring-opening polymerization with the commercial availability of the beta hydroxy acid, 3-hydroxypropionic acid which is abbreviated as 3-HP. Since 3-HPA can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HPA), is biorenewable.

Genetically encoded 3-hydroxypropionic acid inducible system

3-Hydroxypropionic acid can be produced by engineered microbes. [8]

A genetically encoded 3-hydroxypropionic acid inducible system has been characterized in bacteria demonstrating that such system in combination with fluorescent reporter protein can be utilized as a biosensor to measure intracellular and extracellular 3-HP concentrations by fluorescence output. [9]

See also

Related Research Articles

Hydrolysis is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.

<span class="mw-page-title-main">Acetyl-CoA</span> Chemical compound

Acetyl-CoA is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle to be oxidized for energy production.

Lactones are cyclic carboxylic esters are intramolecular esters derived from hydroxycarboxylic acids. They can be saturated or unsaturated. Some contain heteroatoms replacing one or more carbon atoms of the ring.

<span class="mw-page-title-main">Cellulase</span> Class of enzymes

Cellulase is any of several enzymes produced chiefly by fungi, bacteria, and protozoans that catalyze cellulolysis, the decomposition of cellulose and of some related polysaccharides:

<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Polyhydroxyalkanoates</span> Polyester family

Polyhydroxyalkanoates or PHAs are polyesters produced in nature by numerous microorganisms, including through bacterial fermentation of sugars or lipids. When produced by bacteria they serve as both a source of energy and as a carbon store. More than 150 different monomers can be combined within this family to give materials with extremely different properties. These plastics are biodegradable and are used in the production of bioplastics.

<span class="mw-page-title-main">Polylactic acid</span> Biodegradable polymer

Polylactic acid, also known as poly(lactic acid) or polylactide (PLA), is a thermoplastic polyester with backbone formula (C
3
H
4
O
2
)
n
or [–C(CH
3
)HC(=O)O–]
n
, formally obtained by condensation of lactic acid C(CH
3
)(OH)HCOOH
with loss of water. It can also be prepared by ring-opening polymerization of lactide [–C(CH
3
)HC(=O)O–]
2
, the cyclic dimer of the basic repeating unit.

<span class="mw-page-title-main">Polyester</span> Category of polymers, in which the monomers are joined together by ester links

Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

Alpha hydroxy carboxylic acids, or α-hydroxy carboxylic acids (AHAs), are a group of carboxylic acids featuring a hydroxy group located one carbon atom away from the acid group. This structural aspect distinguishes them from beta hydroxy acids, where the functional groups are separated by two carbon atoms. Notable AHAs include glycolic acid, lactic acid, mandelic acid, and citric acid.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

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

Gentiobiose is a disaccharide composed of two units of D-glucose joined with a β(1->6) linkage. It is a white crystalline solid that is soluble in water or hot methanol. Gentiobiose is incorporated into the chemical structure of crocin, the chemical compound that gives saffron its color. It is a product of the caramelization of glucose. During a starch hydrolysis process for glucose syrup, gentiobiose, which has bitterness, is formed as an undesirable product through the acid-catalyzed condensation reaction of two D-glucose molecules. One β-D-glucose unit elongation of the bitter disaccharide reduces its bitterness by a fifth, as determined by human volunteers using the trimer, gentiotriose. Gentiobiose is also produced via enzymatic hydrolysis of glucans, including pustulan and β-1,3-1,6-glucan.

β-Propiolactone Chemical compound

β-Propiolactone, often simply called propiolactone, is an organic compound with the formula CH2CH2CO2. It is a lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents. The carcinogenicity of this compound has limited its commercial applications.

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).

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

γ-Valerolactone Chemical compound

γ-Valerolactone (GVL) or gamma-valerolactone is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.

<span class="mw-page-title-main">Polyaspartic acid</span> Chemical compound

Polyaspartic acid (PASA) is a biodegradable, water-soluble condensation polymer based on the amino acid aspartic acid. It is a biodegradable replacement for water softeners and related applications. PASA can be chemically crosslinked with a wide variety of methods to yield PASA hydrogels. The resulting hydrogels are pH-sensitive such that under acidic conditions, they shrink, while the swelling capacity increases under alkaline conditions.

<span class="mw-page-title-main">Vinylsulfonic acid</span> Chemical compound

Vinylsulfonic acid is the organosulfur compound with the chemical formula CH2=CHSO3H. It is the simplest unsaturated sulfonic acid. The C=C double bond is a site of high reactivity. Polymerization gives polyvinylsulfonic acid, especially when used as a comonomer with functionalized vinyl and (meth)acrylic acid compounds. It is a colorless, water-soluble liquid, although commercial samples can appear yellow or even red.

<span class="mw-page-title-main">2-Ethyl-2-oxazoline</span> Chemical compound

2-Ethyl-2-oxazoline (EtOx) is an oxazoline which is used particularly as a monomer for the cationic ring-opening polymerization to poly(2-alkyloxazoline)s. This type of polymers are under investigation as readily water-soluble and biocompatible materials for biomedical applications.

<span class="mw-page-title-main">Diethyl acetamidomalonate</span> Chemical compound

Diethyl acetamidomalonate (DEAM) is a derivative of malonic acid diethyl ester. Formally, it is derived through the acetylation of ester from the unstable aminomalonic acid. DEAM serves as a starting material for racemates including both, natural and unnatural α-amino acids or hydroxycarboxylic acids. It is also usable as a precursor in pharmaceutical formulations, particularly in the cases of active ingredients like fingolimod, which is used to treat multiple sclerosis.

References

  1. Merck Index, 11th Edition, 4681.
  2. 1 2 Handbook of Chemistry and Physics, CRC press, 58th edition page D150-151 (1977)
  3. Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507. ISBN   978-3527306732.
  4. 1 2 Mika, László T.; Cséfalvay, Edit; Németh, Áron (2018). "Catalytic Conversion of Carbohydrates to Initial Platform Chemicals: Chemistry and Sustainability". Chemical Reviews. 118 (2): 505–613. doi:10.1021/acs.chemrev.7b00395. PMID   29155579.
  5. 1 2 Bozell, Joseph J.; Petersen, Gene R. (2010). "Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's "Top 10" revisited". Green Chemistry. 12 (4): 539. doi:10.1039/b922014c.
  6. Liu, Changshui; Ding, Yamei; Xian, Mo; Liu, Min; Liu, Huizhou; Ma, Qingjun; Zhao, Guang (2017). "Malonyl-CoA pathway: A promising route for 3-hydroxypropionate biosynthesis". Critical Reviews in Biotechnology. 37 (7): 933–941. doi:10.1080/07388551.2016.1272093. PMID   28078904.
  7. "3-HP" . Retrieved 27 May 2011.
  8. "Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide". 27 March 2013.
  9. Hanko, E.K.R.; Minton, N.P.; Malys, N. (2017). "Characterisation of a 3-hydroxypropionic acid-inducible system from Pseudomonas putida for orthogonal gene expression control in Escherichia coli and Cupriavidus necator". Scientific Reports. 7 (1724): 1724. Bibcode:2017NatSR...7.1724H. doi:10.1038/s41598-017-01850-w. PMC   5431877 . PMID   28496205.