3-Hydroxypropionic acid is a

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.9. It is very soluble in water, soluble in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

and

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

. Upon distillation, it dehydrates to form

acrylic acid Acrylic acid (IUPAC: prop-2-enoic 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 ...

, and is occasionally called hydracrylic acid 3-Hydroxypropionic acid is used in the industrial production of various chemicals such as

acrylate Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion . Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain ...

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. Propiolactone, the dehydrated derivative of 3-hydroxypropionic acid, is produced by reaction of

ketene In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary valence (chemistry), monovalent functional group, chemical groups (or two separate Substituent, substitution sites in the same molecule). The na ...

and

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

. 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 Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

, but this technology has not reached a commercial stage. It can also be produced from glucose via pyruvate and malonyl coenzyme A.

Potential applications

3-Hydroxypropionic acid is of interest as a bio-derived precursor to

. The

polyester Polyester is a category of polymers that contain one or two ester linkages 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 some natura ...

poly(3-hydroxypropionic acid) is a biodegradable polymer. 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 A microorganism, or microbe, is an organism of microscopic size, which may exist in its single-celled form or as a colony of cells. The possible existence of unseen microbial life was suspected from antiquity, with an early attestation in ...

. 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.

References

External links

* {{DEFAULTSORT:Hydroxypropanoic acid, 3- Beta hydroxy acids Propionic acids

Synthesis

Potential applications

Genetically encoded 3-hydroxypropionic acid inducible system

See also

References

External links