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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 373031410 |
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| ImageFile = LPAC.svg |
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| ImageFile = LPAC.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageName = LPAC |
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| ImageName = LPAC |
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| IUPACName = 1-hydroxy-1-phenyl-propan-2-one |
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| IUPACName = 1-hydroxy-1-phenyl-propan-2-one |
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| OtherNames = L-PAC<br>(R)-PAC |
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| OtherNames = {{smallcaps|l}}-PAC<br>(R)-PAC |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| | PubChem = 92733 |
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| CASNo =1798-60-3 |
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| SMILES = CC(=O)(C1=CC=CC=C1)O |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 7V3493I8FQ |
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| PubChem = 92733 |
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| SMILES = CC(=O)(C1=CC=CC=C1)O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8096061 |
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| ChEBI = 149766 |
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| InChI = 1/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1 |
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| InChIKey = ZBFFNPODXBJBPW-VIFPVBQEBH |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZBFFNPODXBJBPW-VIFPVBQESA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=9 | H=10 | O=2 |
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| Formula = C<sub>9</sub>H<sub>10</sub>O<sub>2</sub> |
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| Appearance = Yellow-green liquid |
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| MolarMass = 150.174 g/mol |
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| Density = 1.119 g/cm<sup>3</sup> |
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| Appearance = |
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| Density = |
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| MeltingPtC = 9-11 |
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| MeltingPt_ref = <ref>{{Cite web | url = http://synquestlabs.com/product/id/78258.html | title = 1-Phenyl-1-hydroxypropan-2-one }}</ref> |
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| MeltingPt = |
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| BoilingPt = |
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| BoilingPtC = 253 |
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| Solubility = |
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| Solubility = Insoluble |
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| SolubleOther = Freely soluble in alcohols, ether, and aromatic solvents |
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| Solvent = other solvents |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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] |
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'''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 ]. |
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'''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 ]. |
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== Nomenclature == |
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== Nomenclature == |
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(R)-PAC or (R)-(−)-phenylacetylcarbinol is identical to {{smallcaps|l}}-PAC, referring to the outdated ]. |
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(''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. |
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<ref>Rosche et al. Appl Microbiol and Biotechnol; Vol. 57, Nr 3 (2001), pp 309-315; {{doi|10.1007/s002530100781}}</ref> |
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(R)-PAC is the ] isomer of phenylacetylcarbinol. |
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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. |
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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. |
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==Production== |
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==Production== |
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(''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. |
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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> |
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The majority of L-PAC is generated in pharmaceutical plants in ], as an intermediate precursor in the production of pseudoephedrine. |
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The majority of L-PAC is generated in pharmaceutical plants in ], as an intermediate precursor in the production of pseudoephedrine. |
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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> |
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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> |
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==References== |
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==References== |
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