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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 373031410
| ImageFile = LPAC.svg | ImageFile = LPAC.svg
| ImageSize = | ImageSize =
| ImageName = LPAC | ImageName = LPAC
| IUPACName = 1-hydroxy-1-phenyl-propan-2-one | IUPACName = 1-hydroxy-1-phenyl-propan-2-one
| OtherNames = L-PAC<br>(R)-PAC | OtherNames = {{smallcaps|l}}-PAC<br>(R)-PAC
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| | PubChem = 92733
| CASNo =1798-60-3
| SMILES = CC(=O)(C1=CC=CC=C1)O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7V3493I8FQ
| PubChem = 92733
| SMILES = CC(=O)(C1=CC=CC=C1)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8096061
| ChEBI = 149766
| InChI = 1/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1
| InChIKey = ZBFFNPODXBJBPW-VIFPVBQEBH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZBFFNPODXBJBPW-VIFPVBQESA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=9 | H=10 | O=2
| Formula = C<sub>9</sub>H<sub>10</sub>O<sub>2</sub>
| Appearance = Yellow-green liquid
| MolarMass = 150.174 g/mol
| Density = 1.119 g/cm<sup>3</sup>
| Appearance =
| Density = | MeltingPtC = 9-11
| MeltingPt_ref = <ref>{{Cite web | url = http://synquestlabs.com/product/id/78258.html | title = 1-Phenyl-1-hydroxypropan-2-one }}</ref>
| MeltingPt =
| BoilingPt = | BoilingPtC = 253
| Solubility = | Solubility = Insoluble
| SolubleOther = Freely soluble in alcohols, ether, and aromatic solvents
| Solvent = other solvents
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


]
'''Phenylacetylcarbinol''' ('''PAC''') is an organic compound that has two ]s, one with ] and one with S-configuration. (R)-PAC, which is commonly called '''L-PAC''', is known as a ] in the synthesis of pharmaceuticals such as ] and ]. '''Phenylacetylcarbinol''' ('''PAC''') is an organic compound that has two ]s, one with ] and one with S-configuration. (R)-PAC, which is commonly called '''{{smallcaps|l}}-PAC''', is known as a ] in the synthesis of pharmaceuticals such as ] and ].


== Nomenclature == == Nomenclature ==


(R)-PAC or (R)-(−)-phenylacetylcarbinol is identical to {{smallcaps|l}}-PAC, referring to the outdated ]. (''R'')-PAC or (''R'')-(−)-phenylacetylcarbinol is identical to {{smallcaps|l}}-PAC, referring to the outdated ].<ref>{{cite journal | doi = 10.1007/s002530100781| title = Biotransformation of benzaldehyde into ( R )-phenylacetylcarbinol by filamentous fungi or their extracts| journal = Applied Microbiology and Biotechnology| volume = 57| issue = 3| pages = 309–315| year = 2001| last1 = B| first1 = Rosche| last2 = V| first2 = Sandford| last3 = M| first3 = Breuer| last4 = B| first4 = Hauer| last5 = P| first5 = Rogers}}</ref> (''R'')-PAC is the ] isomer of phenylacetylcarbinol.
<ref>Rosche et al. Appl Microbiol and Biotechnol; Vol. 57, Nr 3 (2001), pp 309-315; {{doi|10.1007/s002530100781}}</ref>
(R)-PAC is the ] isomer of phenylacetylcarbinol.


The IUPAC name of phenylacetylcarbinol is 1-hydroxy-1-phenylpropan-2-one. Synonyms are 1-hydroxy-1-phenyl-2-propanone and 1-Hydroxy-1-phenylacetone. The IUPAC name of phenylacetylcarbinol is 1-hydroxy-1-phenylpropan-2-one. Synonyms are 1-hydroxy-1-phenyl-2-propanone and 1-Hydroxy-1-phenylacetone.


==Production== ==Production==
(''R'')-PAC is widely synthesized by fermentation of ] and ]. In this process, colonies of ] (in particular, strains such as '']'', '']'', or '']'') are cultivated and added to a broth of water, ], and the enzyme ] in a vat. The yeast is left to grow for a period of time, after which the ] is introduced into the broth. The yeast then ferments the benzaldehyde into (''R'')-PAC.<ref> {{webarchive|url=https://web.archive.org/web/20060622070604/http://www.agro.cmu.ac.th/department/fe/JANoppol/NoppolThesis.pdf |date=2006-06-22 }}</ref> Boiling point at 12mmHg is 124-125C.

L-PAC is widely synthesized by fermentation of ] and ]. In this process, colonies of ] (in particular, strains such as ], ], or ]) are cultivated and added to a broth of water, ], and the enzyme ] in a vat. The yeast is left to grow for a period of time, after which the ] is introduced into the broth. The yeast then ferments the benzaldehyde into L-PAC.<ref></ref>


The majority of L-PAC is generated in pharmaceutical plants in ], as an intermediate precursor in the production of pseudoephedrine. The majority of L-PAC is generated in pharmaceutical plants in ], as an intermediate precursor in the production of pseudoephedrine.


There are also biochemical reactions where enzymes such as Acetohydroxyacid Synthase I <ref>]</ref> from ''E. coli'' condense pyruvate and benzaldehyde into R-PAC. Such methods have much higher conversion rates in comparison to the conventional yeast fermentation.<ref></ref> There are also biochemical reactions where enzymes such as acetohydroxyacid synthase I from ''E. coli'' condense pyruvate and benzaldehyde into R-PAC. Such methods have much higher conversion rates in comparison to the conventional yeast fermentation.<ref>{{cite journal | doi = 10.1002/bit.20392 | pmid = 15685598 | title = Column flow reactor using acetohydroxyacid synthase I from ''Escherichia'' coli as catalyst in continuous synthesis of R-phenylacetyl carbinol | journal = Biotechnology and Bioengineering | volume = 89 | issue = 6 | pages = 733–740 | year = 2005 | last1 = Engel | first1 = Stanislav | last2 = Vyazmensky | first2 = Maria | last3 = Berkovich | first3 = Dvora | last4 = Barak | first4 = Ze'ev | last5 = Merchuk | first5 = Jose | last6 = Chipman | first6 = David M. | doi-access = free }}</ref>


==References== ==References==
<references/> <references/>


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