Cannabis Compound Database: Showing Compound Card for Benzophenone (CDB000564)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 4 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:43:58 UTC

Updated at

2020-12-07 19:07:31 UTC

CannabisDB ID

CDB000564

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Benzophenone

Description

Benzophenone, also known as alpha-oxoditane or diphenyl ketone, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. The chemical formula of benzophenone is (C6H5)2CO, generally abbreviated to Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is found in fruits, such as grapes. It is used as an additive in flavorings or perfumes for "sweet-woody-geranium‚Äù-like notes. Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100% efficiency. The resulting diradical will subtract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Benzophenone can be used as a photo initiator in UV-curing applications such as inks, imaging, and clear coatings in the printing industry. Benzophenone can also serve as a preservative from ultraviolet (UV) light, preventing damage to scents and colors in products such as perfumes and soaps. Although it is considered as "essentially nontoxic‚Äù, benzophenone has been found to be an endocrine disruptor capable of binding to the pregnane X receptor (PMID: 14613717 ). Benzophenone 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 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
alpha-Oxodiphenylmethane	ChEBI
alpha-Oxoditane	ChEBI
Benzoylbenzene	ChEBI
Diphenyl ketone	ChEBI
DIPHENYLMETHANONE	ChEBI
PH2CO	ChEBI
a-Oxodiphenylmethane	Generator
Α-oxodiphenylmethane	Generator
a-Oxoditane	Generator
Α-oxoditane	Generator
1DZP	HMDB
Adjutan 6016	HMDB
ADK stab 1413	HMDB
alpha -Oxodiphenylmethane	HMDB
alpha -Oxoditane	HMDB
Benzopheneone	HMDB
BENZOPHENONE (8ci)	HMDB
Benzophenone (diphenyl-ketone)	HMDB
Benzoyl-benzene	HMDB
BZQ	HMDB
Di(phenyl)methanone	HMDB
Diphenyl-methanon	HMDB
Diphenyl-methanone	HMDB
Diphenylketone	HMDB
Diphenylmethanone, 9ci	HMDB
FEMA 2134	HMDB
Kayacure BP	HMDB
Ketone, diphenyl	HMDB
METHANONE, diphenyl- (9ci)	HMDB
Phenyl ketone	HMDB

Chemical Formula

C₁₃H₁₀O

Average Molecular Weight

182.22

Monoisotopic Molecular Weight

182.0732

IUPAC Name

diphenylmethanone

Traditional Name

benzophenone

CAS Registry Number

119-61-9

SMILES

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

InChI Identifier

InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

InChI Key

RWCCWEUUXYIKHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Aryl-phenylketone
Diphenylmethane
Aryl ketone
Benzoyl
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones (CHEBI:41308 )

Ontology

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	26 °C	Not Available
Boiling Point	305.4 °C	Wikipedia
Water Solubility	0.14 mg/mL at 25 °C	Not Available
logP	3.18	Not Available

Predicted Properties

Property	Value	Source
logP	3.03	ALOGPS
logP	3.43	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-7.5	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	2	ChemAxon
Refractivity	56.63 m³·mol⁻¹	ChemAxon
Polarizability	20.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-6900000000-e66f1faddf56bc55ae47	2014-09-20	View Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-b948527870febd59c85e	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-4900000000-93e6c7526327719d728d	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a4i-3900000000-23d78741cacbe9443a57	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-eb0842414a2a12ff24b3	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-7c028c0aa3b44d2ee6be	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-b948527870febd59c85e	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-4900000000-93e6c7526327719d728d	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a4i-3900000000-23d78741cacbe9443a57	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-eb0842414a2a12ff24b3	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20	Spectrum
GC-MS	Benzophenone, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-7c028c0aa3b44d2ee6be	Spectrum
Predicted GC-MS	Benzophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a59-3900000000-94e3675023c8e5cf8b46	Spectrum
Predicted GC-MS	Benzophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-1f9db6636ef926e9a822	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0a4i-0900000000-c08dc4bd854f23a10ab6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-0900000000-1f9db6636ef926e9a822	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-f048592c39e6448959f3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-0900000000-35d1d32df051465b3618	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3900000000-4e792aa67452f41d4fd0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-2ea2893ee5ce1f203589	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-fb40d9e5c26915affa0d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-7900000000-d9d95ec382ac97a7af66	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-052cd8aa2cc34939880f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-0900000000-f0b9223dd578ae5d011f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9200000000-4239c3243d5a26b7658f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-2aea314e447f6c21a0a5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-81ba80bd5ec599f30980	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-2900000000-2142e08d17da4d6f92a3	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 2	NR1I2	3q12-q13.3	O75469	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 2	NR1I2	3q12-q13.3	O75469	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 2	NR1I2	3q12-q13.3	O75469	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 2	NR1I2	3q12-q13.3	O75469	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0032049

DrugBank ID

DB01878

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

Benzophenone

METLIN ID

Not Available

PubChem Compound

3102

PDB ID

BZQ

ChEBI ID

41308

References

General References

Mikamo E, Harada S, Nishikawa J, Nishihara T: Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor. Toxicol Appl Pharmacol. 2003 Nov 15;193(1):66-72. doi: 10.1016/j.taap.2003.08.001. [PubMed:14613717 ]
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 ]

Enzymes

Enzyme Details

1. Nuclear receptor subfamily 1 group I member 2

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular weight:: 49761.2

Showing Compound Card for Benzophenone (CDB000564)

Structure for CDB000564 (Benzophenone)

Enzymes