Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:09:59 UTC |
---|
Update date | 2020-09-17 15:34:39 UTC |
---|
Primary ID | FDB012106 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Acetophenone |
---|
Description | Acetophenone, also known as 1-phenylethanone or acetylbenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. The chemical formula of acetophenone is C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is used as a flavouring ingredient for fruit flavours and as a leavening agent. Acetophenone is also the starting material for the synthesis of some pharmaceuticals and is listed as an approved excipient by the U.S. FDA. Acetophenone is currently listed as a Group D carcinogen indicating that it does not produce carcinogenic effects in humans. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes. Acetophenone is found in many foods, some of which are chicory, spearmint, watermelon, rocket salad, and pepper (spice), apple, cheese, apricot, banana, beef, and cauliflower. |
---|
CAS Number | 98-86-2 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
1-Phenylethanone | ChEBI | Acetylbenzene | ChEBI | Benzoyl methide | ChEBI | Methyl phenyl ketone | ChEBI | Phenyl methyl ketone | ChEBI | 1-Phenyl-1-ethanone | HMDB | 1-Phenyl-ethanone | HMDB | 1-Phenylethan-1-one | HMDB | 1-Phenylethanone (acetophenone) | HMDB | 1-Phenylethanone, 9ci | HMDB | Acetofenon | HMDB | Acetophenon | HMDB | Acetyl-benzene | HMDB | Acetylbenzol | HMDB | alpha-Acetophenone | HMDB | Benzoylmethide | HMDB | Dymex | HMDB | FEMA 2009 | HMDB | Hypnon | HMDB | Hypnone | HMDB | Ketone, methyl phenyl | HMDB | Methyl phenyl-ketone | HMDB | Methylphenylketone | HMDB | Nchem.180-comp5 | HMDB | Phenyl | HMDB | Phenylethanone | HMDB | Phenylmethylketone | HMDB | α-acetophenone | biospider | 1-phenylethan-1-one | biospider | 1-Phenylethanone, 9CI | db_source | Benzene, acetyl- | biospider | Ethanone, 1-phenyl- | biospider | Ketone, methyl phenyl- | biospider | nchem.180-comp5 | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C8H8O |
---|
IUPAC name | 1-phenylethan-1-one |
---|
InChI Identifier | InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
---|
InChI Key | KWOLFJPFCHCOCG-UHFFFAOYSA-N |
---|
Isomeric SMILES | CC(=O)C1=CC=CC=C1 |
---|
Average Molecular Weight | 120.1485 |
---|
Monoisotopic Molecular Weight | 120.057514878 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbonyl compounds |
---|
Direct Parent | Alkyl-phenylketones |
---|
Alternative Parents | |
---|
Substituents | - Alkyl-phenylketone
- Acetophenone
- Aryl alkyl ketone
- Benzoyl
- Benzenoid
- Monocyclic benzene moiety
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Environmental role: Industrial application: Biological role: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Liquid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 79.97%; H 6.71%; O 13.32% | DFC |
---|
Melting Point | Mp 20° | DFC |
---|
Boiling Point | Bp5 67° | DFC |
---|
Experimental Water Solubility | 6.13 mg/mL at 25 oC | SOUTHWORTH,GR & KELLER,JL (1986) |
---|
Experimental logP | 1.58 | HANSCH,C ET AL. (1995) |
---|
Experimental pKa | pKa1 -6.4 (25°, H2SO4 aq.) | DFC |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | d204 1.03 | DFC |
---|
Refractive Index | n20D 1.5342 | DFC |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9700000000-224496fb4a326cb28b65 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9800000000-5d4a6da80c6c3c5f5fbb | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-8900000000-72a8572391def7a73d00 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0pdi-9600000000-d687340f90f63f7dc2db | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0pdi-9500000000-3f26e145dcae1ef98802 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9600000000-558d4c95783742599522 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0adi-9700000000-6f2471f8e98524af3f5b | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0fr2-1900000000-a41b0cedd919c67e41f4 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9700000000-224496fb4a326cb28b65 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9800000000-5d4a6da80c6c3c5f5fbb | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-8900000000-72a8572391def7a73d00 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0pdi-9600000000-d687340f90f63f7dc2db | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0pdi-9500000000-3f26e145dcae1ef98802 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0a6r-9600000000-558d4c95783742599522 | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0adi-9700000000-6f2471f8e98524af3f5b | Spectrum | GC-MS | Acetophenone, non-derivatized, GC-MS Spectrum | splash10-0fr2-1900000000-a41b0cedd919c67e41f4 | Spectrum | Predicted GC-MS | Acetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0pi0-9700000000-60050b91c62443766d21 | Spectrum | Predicted GC-MS | Acetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-7c012935d15ff7510bb2 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-2aa01ede85e5b5caa8d8 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-6900000000-d47a5846f1d60b451390 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-ba5d67d7d79e78cf111e | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-2900000000-b904a793250c40e784a3 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9400000000-f72df069d2851aa2de2a | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-9fe47ad4ae02d8640b56 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-016r-5900000000-bb7919a9d31b496bf441 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fbc-9100000000-9e7d314dd7e6128835bc | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9200000000-9aee9a6157b9ef0e6d58 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-66cb89e73dbfd10f0117 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-a1759373fa5762f762e4 | 2021-09-24 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | 7132 |
---|
ChEMBL ID | CHEMBL274467 |
---|
KEGG Compound ID | C07113 |
---|
Pubchem Compound ID | 7410 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 27632 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB04619 |
---|
HMDB ID | HMDB33910 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | HDG06-B:HDG06-B |
---|
EAFUS ID | 26 |
---|
Dr. Duke ID | ACETOPHENONE|METHYL-PHENYLKETONE |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002685 |
---|
HET ID | AC0 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | 98-86-2 |
---|
GoodScent ID | rw1000131 |
---|
SuperScent ID | 7410 |
---|
Wikipedia ID | Acetophenone |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
must |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| flower |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| almond |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| hawthorne |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| sweet |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| pungent |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| hawthorn |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| mimosa |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| acacia |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| chemical |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
|
|
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|