Cannabis Compound Database: Showing Compound Card for Benzaldehyde (CDB000562)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 3 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:43:51 UTC

Updated at

2020-12-07 19:07:31 UTC

CannabisDB ID

CDB000562

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Benzaldehyde

Description

Benzaldehyde, also known as benzenecarbonal or benzenemethylal, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Benzaldehyde is a colorless liquid with a characteristic almond-like odor. It is a strong, sweet, and almond tasting compound. Benzaldehyde is found, on average, in the highest concentration within a few different foods, such as black walnuts, almonds, and corns and in a lower concentration in safflowers, kohlrabis, and ceylon cinnamons. Benzaldehyde has also been detected, but not quantified in, Mexican oregano, winter savories, strawberries, lingonberries, and common persimmons. Benzaldehyde has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. It is currently used in only seven cosmetic products, with the highest reported used concentration of 0.5 %, in perfumes. Benzaldehyde is a ‚ÄúGenerally Regarded As Safe‚Äù (GRAS) food additive in the U.S.A. and is accepted as a flavoring substance in the European Union. Although there is limited data available in regards of potential skin irritation and sensitization caused by benzaldehyde, the available data on the safety of the use of benzoic acid is currently used to support the safe use of benzaldehyde. (PMID: 16835129 , Int J Toxicol. 2006;25 Suppl 1:11-27.). This is because benzaldehyde rapidly metabolizes to benzoic acid in the skin, rendering the available dermal irritation and sensitization data on the latter sufficient to support the safety of Benzaldehyde. Benzaldehyde is absorbed through the skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Several studies have suggested that benzaldehyde can have carcinostatic or antitumor properties ( Ref:DOI ). Overall, at the concentrations used in cosmetics, benzaldehyde is not considered a carcinogenic risk to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Artificial almond oil	ChEBI
Benzanoaldehyde	ChEBI
Benzene carbaldehyde	ChEBI
Benzene carboxaldehyde	ChEBI
Benzenecarbonal	ChEBI
Benzenecarboxaldehyde	ChEBI
Benzenemethylal	ChEBI
Benzoic acid aldehyde	ChEBI
Benzoic aldehyde	ChEBI
Benzylaldehyde	ChEBI
Ethereal oil OF bitter almonds	ChEBI
Phenylformaldehyde	ChEBI
Phenylmethanal	ChEBI
Synthetic oil OF bitter almond	ChEBI
Benzoate aldehyde	Generator
Almond artificial essential oil	HMDB
Artificial bitter almond oil	HMDB
Artificial essential oil OF almond	HMDB
Benzadehyde	HMDB
Benzaldehyde FFC	HMDB
Benzene methylal	HMDB
Benzoate	HMDB
Benzoic acid	HMDB
Benzoyl hydride	HMDB
Benzyaldehyde	HMDB
BEZ	HMDB
Caswell no. 076	HMDB
FEMA no. 2127	HMDB
Oil OF bitter almond	HMDB
Phenylmethanal benzenecarboxaldehyde	HMDB
Benzaldehyde, formyl-(14)C-labeled	MeSH, HMDB

Chemical Formula

C₇H₆O

Average Molecular Weight

106.12

Monoisotopic Molecular Weight

106.0419

IUPAC Name

benzaldehyde

Traditional Name

benzaldehyde

CAS Registry Number

100-52-7

SMILES

O=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

InChI Key

HUMNYLRZRPPJDN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoyl derivatives

Direct Parent

Benzoyl derivatives

Alternative Parents

Substituents

Benzoyl
Benzaldehyde
Aryl-aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzaldehydes (CHEBI:17169 )
an aryl aldehyde (BENZALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Plant:

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Food and nutrition:

Flavoring agent

Personal care products:

Perfuming agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-26 °C	Not Available
Boiling Point	178.1 °C	Wikipedia
Water Solubility	6.95 mg/mL at 25 °C	Not Available
logP	1.48	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.6	ALOGPS
logP	1.69	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-7.1	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	32.64 m³·mol⁻¹	ChemAxon
Polarizability	11.02 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0pdi-9600000000-2c76a7cdbd4023dd3eff	2015-03-01	View Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-731755b6449c9d44f340	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-7900000000-7d98ce9e964eb9bae123	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-9700000000-af6ef18ad5441da71000	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0pdi-9500000000-eee2fac3cee7076204ca	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-731755b6449c9d44f340	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-7900000000-7d98ce9e964eb9bae123	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0a6r-9700000000-af6ef18ad5441da71000	Spectrum
GC-MS	Benzaldehyde, non-derivatized, GC-MS Spectrum	splash10-0pdi-9500000000-eee2fac3cee7076204ca	Spectrum
Predicted GC-MS	Benzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9800000000-930ad158d75deff2317a	Spectrum
Predicted GC-MS	Benzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-056r-9400000000-d5e049f5a5c77b8864cb	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9100000000-dca76d402f152bd3f562	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9100000000-ce8274b57c274e79f894	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-0a6r-9600000000-731755b6449c9d44f340	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0a6r-7900000000-7d98ce9e964eb9bae123	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0a6r-9700000000-e4f830b1b36028903665	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-0pdi-9500000000-eee2fac3cee7076204ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-2900000000-effe07b6b286033801ed	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-6345a1cf40f283a793a2	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-296abcf15a77a1f53d6a	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9200000000-086efee77b92115c17ca	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-266f38215789f236324e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-266f38215789f236324e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-828e61a7919a0eb81940	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2900000000-18b3fa1f2954aac5b323	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9500000000-66c17c5a52895b2cc4d3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-8900000000-aae71de8ab13b4993f86	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-84ecaabc5b5d7c2807f5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-99509376f83dc0a53432	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldehyde dehydrogenase family 8 member A1	ALDH8A1	6q23.2	Q9H2A2	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0006115

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Benzaldehyde

METLIN ID

Not Available

PubChem Compound

240

PDB ID

Not Available

ChEBI ID

17169

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 ]
Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. doi: 10.1080/10915810600716612. [PubMed:16835129 ]

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase family 8 member A1

General function:: Involved in oxidoreductase activity
Specific function:: Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro)
Gene Name:: ALDH8A1
Uniprot ID:: Q9H2A2
Molecular weight:: 53400.9

Showing Compound Card for Benzaldehyde (CDB000562)

Structure for CDB000562 (Benzaldehyde)

Enzymes