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Revision as of 17:53, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470548077 of page 3-Hydroxypropionic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 16:30, 1 May 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,495 edits →Synthesis: prep 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| verifiedrevid = 443653820 |verifiedrevid = 477218961
| Reference=<ref name="Merck">''Merck Index'', 11th Edition, '''4681'''.</ref> |Reference=<ref name="Merck">''Merck Index'', 11th Edition, '''4681'''.</ref>
| Name = 3-Hydroxypropionic acid |Name = 3-Hydroxypropionic acid
| ImageFile = 3-Hydroxypropanoic acid.png |ImageFile = 3-Hydroxypropionic-acid-2D-skeletal.svg
| ImageSize = 170px |ImageSize = 200px
| ImageName = Skeletal formula |ImageName = Skeletal formula
| ImageFile1 = 3-hydroxypropionic-acid-3D-balls.png |ImageFile1 = 3-hydroxypropionic-acid-3D-balls.png
| ImageSize1 = 210px |ImageSize1 = 210px
| ImageName1 = Ball-and-stick model |ImageName1 = Ball-and-stick model
| IUPACName = 3-Hydroxypropanoic acid |PIN = 3-Hydroxypropanoic acid
| OtherNames = 3-hydroxypropionic acid<br />hydracrylic acid<br />ethylene lactic acid |OtherNames = 3-Hydroxypropionic acid<br />Hydracrylic acid<br />Ethylene lactic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61460 | ChemSpiderID = 61460
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 503-66-2 | CASNo = 503-66-2
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33404 | ChEBI = 33404
| ChEMBL = 1205969
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03688 | DrugBank = DB03688
| EINECS = 207-974-8
| PubChem = 68152
| UNII = C4ZF6XLD2X
| 3DMet = B00221
| Beilstein = 773806
| SMILES = O=C(O)CCO | SMILES = O=C(O)CCO
⚫ }}
⚫ | Section2 = {{Chembox Properties
⚫ | Formula = C<sub>3</sub>H<sub>6</sub>O<sub>3</sub>
⚫ | MolarMass = 90.08 g/mol
| Density =
⚫ | MeltingPt = <25 °C<br>143 °C (sodium salt)
⚫ | BoilingPt = Decomposes
⚫ | Solubility = Very soluble
⚫ }}
⚫ | Section4 = {{Chembox Related
⚫ | Function = ]s
⚫ | OtherFunctn = ]<br />]<br />]<br />]<br />]<br />]<br />]
⚫ | OtherCpds = ]<br />]<br />]<br />]
}} }}
⚫ |Section2={{Chembox Properties
⚫ |Formula = C<sub>3</sub>H<sub>6</sub>O<sub>3</sub>
⚫ |MolarMass = 90.08 g/mol
⚫ |MeltingPt = <25 °C<br>143 °C (sodium salt)
⚫ |BoilingPt = Decomposes
⚫ |Solubility = Very soluble
|pKa = 4.87<ref name="CRC">Handbook of Chemistry and Physics, CRC press, 58th edition page D150-151 (1977)</ref>
⚫ }}
⚫ |Section4={{Chembox Related
⚫ |OtherFunction_label = ]s
⚫ |OtherFunction = ]<br />]<br />]<br />]<br />]<br />]<br />]
⚫ |OtherCompounds = ]<br />]<br />]<br />]
⚫ }}
}} }}

'''3-Hydroxypropionic acid''' is a ], specifically a ]. It is an acidic viscous liquid with a ] of 4.9.<ref name="CRC"/> It is very soluble in water, soluble in ] and ]. Upon distillation, it ] to form ], and is occasionally called '''hydracrylic acid'''

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

==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 ] is yet another route.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a13_507|title=Hydroxycarboxylic Acids, Aliphatic|year=2000|last1=Miltenberger|first1=Karlheinz|isbn=3527306730}}</ref> Propiolactone, the dehydrated derivative of 3-hydroxypropionic acid, is produced by reaction of ] and ].<ref name=CR/>

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 ], but this technology has not reached a commercial stage.<ref name=topten>{{cite journal |doi=10.1039/b922014c |title=Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's "Top 10" revisited |date=2010 |last1=Bozell |first1=Joseph J. |last2=Petersen |first2=Gene R. |journal=Green Chemistry |volume=12 |issue=4 |page=539 }}</ref> It can also be produced from glucose via pyruvate and malonyl coenzyme A.<ref name=CR>{{cite journal |doi=10.1021/acs.chemrev.7b00395 |title=Catalytic Conversion of Carbohydrates to Initial Platform Chemicals: Chemistry and Sustainability |date=2018 |last1=Mika |first1=László T. |last2=Cséfalvay |first2=Edit |last3=Németh |first3=Áron |journal=Chemical Reviews |volume=118 |issue=2 |pages=505–613 |pmid=29155579 }}</ref><ref>{{cite journal |doi=10.1080/07388551.2016.1272093 |title=Malonyl-CoA pathway: A promising route for 3-hydroxypropionate biosynthesis |date=2017 |last1=Liu |first1=Changshui |last2=Ding |first2=Yamei |last3=Xian |first3=Mo |last4=Liu |first4=Min |last5=Liu |first5=Huizhou |last6=Ma |first6=Qingjun |last7=Zhao |first7=Guang |journal=Critical Reviews in Biotechnology |volume=37 |issue=7 |pages=933–941 |pmid=28078904 }}</ref>

==Potential applications==
3-Hydroxypropionic acid is of interest as a bio-derived precursor to ].<ref name=topten/>

The ] poly(3-hydroxypropionic acid) is a ].<ref>{{cite web|title=3-HP|url=http://www.license.umn.edu/Products/Biodegradable-Polyester-Produced-From-Non-toxic--Renewable-Monomer__Z05135.aspx|access-date=27 May 2011}}</ref> The method combines the high-molecular weight and control aspects of ] 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 ].<ref>{{Cite web|url=http://www.popsci.com/science/article/2013-03/scientists-are-engineering-volcanic-microorganisms-chew-co2-spit-back-fuel|title = Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide|date = 27 March 2013}}</ref>

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.<ref>{{cite journal|last1=Hanko |first1=E.K.R. |last2=Minton |first2=N.P. |last3=Malys |first3=N. |title=Characterisation of a 3-hydroxypropionic acid-inducible system from ''Pseudomonas putida'' for orthogonal gene expression control in ''Escherichia coli'' and ''Cupriavidus necator'' |journal=Scientific Reports |volume=7 |number=1724 |date=2017 |page=1724 |doi=10.1038/s41598-017-01850-w |pmid=28496205 |pmc=5431877 |bibcode=2017NatSR...7.1724H}}</ref>

==See also==
*] (2-hydroxypropanoic acid)
* listed as hydracrylic acid in the Merck index, 12th Edition

==References==
{{reflist}}

==External links==
*{{cite EB1911|wstitle=Hydracrylic Acid|volume=14|page=34}}

{{DEFAULTSORT:Hydroxypropanoic acid, 3-}}
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