Cannabis Compound Database: Showing Compound Card for Acetophenone (CDB000548)

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Record Information

Version

1.0

Created at

2020-03-19 00:43:06 UTC

Updated at

2020-12-07 19:07:30 UTC

CannabisDB ID

CDB000548

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common 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. Acetophenone has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ) and is a constituent of marijuana smoke ( Ref:DOI ). Acetophenone is volatilized during the combustion of cannabis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₈H₈O

Average Molecular Weight

120.15

Monoisotopic Molecular Weight

120.0575

IUPAC Name

1-phenylethan-1-one

Traditional Name

acetophenone

CAS Registry Number

98-86-2

SMILES

CC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3

InChI Key

KWOLFJPFCHCOCG-UHFFFAOYSA-N

Chemical Taxonomy

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

acetophenones (CHEBI:27632 )
an aromatic compound (PHENYL )
a methyl-ethyl-ketone (PHENYL )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Cucurbitaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Environmental role:

Hazardous air pollutant

Industrial application:

Drug

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	20 °C	Not Available
Boiling Point	202 °C	Wikipedia
Water Solubility	6.13 mg/mL at 25 °C	Not Available
logP	1.58	Not Available

Predicted Properties

Property	Value	Source
logP	1.65	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	16.1	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.46 m³·mol⁻¹	ChemAxon
Polarizability	13.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0033910

DrugBank ID

DB04619

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetophenone

METLIN ID

Not Available

PubChem Compound

7410

PDB ID

AC0

ChEBI ID

27632

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Acetophenone (CDB000548)

Structure for CDB000548 (Acetophenone)