Cannabis Compound Database: Showing Compound Card for Benzoic acid (CDB004927)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:51:20 UTC

Updated at

2022-12-13 23:36:28 UTC

CannabisDB ID

CDB004927

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Benzoic acid

Description

Benzoic acid, also known as benzoate, belongs to the class of organic compounds known as benzoic acids. These are organic compounds containing a benzene ring which bears at least one carboxyl group. Benzoic acid exists as a white solid and is a weakly acidic compound (based on its pKa). The name is derived from gum benzoin, which was for a long time its only source. Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. Benzoic acid is found in all living species, ranging from bacteria to plants to humans. Benzoic acid has a faint, balsam, or urine like odor. Benzoic acid is found naturally in a number of plants and foods, such as American cranberries, bilberries, apples, italian sweet red peppers, and garden onions and in a lower concentration in carrots, dills, and parsnips. Benzoic acid has also been detected, but not quantified in fennels, anise, avocado, cloves, grapefruit, strawberries, olives, plums, red raspberries, Chinese cinnamons, and black pepper (spice). More specifically the benzoic acid content in strawberries is up to 29 mg/kg, cayenne pepper and mustard seeds is up to 10 mg/kg, cloves, salvia, thyme and nutmeg have up to 50 mg/kg and cinnamon has up to 335 mg/kg. Benzoic acid and its salts are widely used as food preservatives. Benzoic acid inhibits the growth of mold, yeast and some bacteria. It is especially useful in carbonated beverages, as it presents its strongest antibacterial activity at pH 2.5–4.0. Benzoic acid is used as a preservative in syrups, fruit salads, icings, jams, jellies, preserves, salted margarine, mincemeat, pickles and relishes, pie, pastry fillings, prepared salads, fruit cocktails, soy sauce, and caviar. The use level ranges from 0.05 to 0.1%. Benzoic acid is also naturally produced in humans when gut bacteria process polyphenols (from ingested fruits or beverages). It often is conjugated to glycine in the liver and excreted as hippuric acid (PMID: 5012256 ). Medically, benzoic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot. Benzoic acid was also used as an expectorant, analgesic, and antiseptic in the early 20th century. Industrially, benzoic acid is an important precursor for the industrial synthesis of many other organic substances and plastics. Benzoic acid in the acid form is quite toxic but its sodium salt is much less toxic. Studies of the subacute toxicity of benzoic acid in mice indicated that ingestion of benzoic acid or its sodium salt caused weight loss, diarrhea, irritation of internal membranes, internal bleeding, enlargement of liver and kidney, hypersensitivity, and paralysis followed by death. Benzoic acid is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide benzoique	ChEBI
Aromatic carboxylic acid	ChEBI
Benzenecarboxylic acid	ChEBI
Benzeneformic acid	ChEBI
Benzenemethanoic acid	ChEBI
Benzoesaeure	ChEBI
Dracylic acid	ChEBI
e210	ChEBI
Phenylcarboxylic acid	ChEBI
Phenylformic acid	ChEBI
Aromatic carboxylate	Generator
Benzenecarboxylate	Generator
Benzeneformate	Generator
Benzenemethanoate	Generator
Dracylate	Generator
Phenylcarboxylate	Generator
Phenylformate	Generator
Benzoate	Generator
Benzenemethonic acid	HMDB
Benzoic acid sodium salt	HMDB
Carboxybenzene	HMDB
Diacylate	HMDB
Diacylic acid	HMDB
Oracylic acid	HMDB
Sodium benzoate	HMDB
Sodium benzoic acid	HMDB
Acid, benzoic	HMDB
Kendall brand OF benzoic acid sodium salt	HMDB
Benzoate, potassium	HMDB
Potassium benzoate	HMDB
Ucephan	HMDB

Chemical Formula

C₇H₆O₂

Average Molecular Weight

122.12

Monoisotopic Molecular Weight

122.0368

IUPAC Name

benzoic acid

Traditional Name

benzoic acid

CAS Registry Number

65-85-0

SMILES

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

InChI Identifier

InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)

InChI Key

WPYMKLBDIGXBTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids

Alternative Parents

Substituents

Benzoic acid
Benzoyl
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoic acids (CHEBI:30746 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Microbe:

Serratia:

Serratia marcescens

Air pollutant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	122.4 °C	Not Available
Boiling Point	250 °C	Wikipedia
Water Solubility	3.4 mg/mL at 25 °C	Not Available
logP	1.87	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.72	ALOGPS
logP	1.63	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.31 m³·mol⁻¹	ChemAxon
Polarizability	11.97 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)	splash10-0pk9-8900000000-3d79c70c455799ab33e3	2014-09-20	View Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0a70-0900000000-5284a0c1c77a1979e1f4	Spectrum
GC-MS	Benzoic acid, 1 TMS, GC-MS Spectrum	splash10-056r-3900000000-1c74c32fa650fcd4cb4d	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-05i0-6900000000-fa50606b2e84fc4cefe9	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-d08dbc757a6de6c3f54e	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0adi-9800000000-40f904bf20072c72a08b	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0pk9-9800000000-b93fc1120a1c74b88fa3	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-05i0-5900000000-1b6bbf98557af374f3a5	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0570-0900000000-ecd208f1e7b4d5ad85f2	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0a70-0900000000-5284a0c1c77a1979e1f4	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-056r-3900000000-1c74c32fa650fcd4cb4d	Spectrum
GC-MS	Benzoic acid, non-derivatized, GC-MS Spectrum	splash10-0a70-0900000000-cec9e1ab69521049d1e4	Spectrum
Predicted GC-MS	Benzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kmi-7900000000-5ad752bd6787261a11d0	Spectrum
Predicted GC-MS	Benzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-7900000000-1c4c0dbbb165ef614f43	Spectrum
Predicted GC-MS	Benzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Benzoic acid, 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)	splash10-00b9-9500000000-f312a552bef1a2927e64	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9100000000-dafd91c9134bc4143743	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00b9-9400000000-29ca905567aa5c59d46b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positive	splash10-05i0-6900000000-fa50606b2e84fc4cefe9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a6r-9600000000-d08dbc757a6de6c3f54e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0adi-9800000000-2693809ae064e720bf58	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pk9-9800000000-2c6be5ecee1848091a24	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-4644ee08861e75d0b808	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00b9-9400000000-11baabb3c0bb283b1c6e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004l-9100000000-4875643627420279223b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-97a21f3206f5c1f0ba7e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-4644ee08861e75d0b808	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00b9-9400000000-11baabb3c0bb283b1c6e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004l-9100000000-4875643627420279223b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-97a21f3206f5c1f0ba7e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-0900000000-94c7f13620a367bf5516	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00di-0900000000-f060e7aa8085ec6be223	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00di-0900000000-a28fdef9c1c00d45c3ff	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-0900000000-3cad9aa6b0980c87bcc3	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-ee9de948bfb30da0a400	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-1900000000-c18a9b04d65d91fdd99e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-9300000000-0878408a026788c942a0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-3900000000-f25040451834faf3bf91	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-9500000000-b352342b60fd48a0c127	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-1d11331d7d21e32dbdba	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (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
Lysosomal acid lipase/cholesteryl ester hydrolase	LIPA	10q23.2-q23.3	P38571	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Liver carboxylesterase 1	CES1	16q22.2	P23141	details
Cocaine esterase	CES2	16q22.1	O00748	details
Acylphosphatase-2	ACYP2	2p16.2	P14621	details
Acylphosphatase-1	ACYP1	14q24.3	P07311	details
Glycine N-acyltransferase	GLYAT	11q12.1	Q6IB77	details
Carboxylesterase 5A	CES5A	16q12.2	Q6NT32	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0456 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0861 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0436 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.0718 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0943 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0225 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0001870

DrugBank ID

DB03793

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30746

References

General References

Tomokuni K, Ogata M: Direct colorimetric determination of hippuric acid in urine. Clin Chem. 1972 Apr;18(4):349-51. [PubMed:5012256 ]

Enzymes

Enzyme Details

1. Lysosomal acid lipase/cholesteryl ester hydrolase

General function:: Involved in lipid metabolic process
Specific function:: Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:: LIPA
Uniprot ID:: P38571
Molecular weight:: 45418.71

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

3. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Enzyme Details

4. Cocaine esterase

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:: CES2
Uniprot ID:: O00748
Molecular weight:: 68898.39

Enzyme Details

5. Acylphosphatase-2

General function:: Involved in acylphosphatase activity
Specific function:: Its physiological role is not yet clear.
Gene Name:: ACYP2
Uniprot ID:: P14621
Molecular weight:: 11139.52

Enzyme Details

6. Acylphosphatase-1

General function:: Involved in acylphosphatase activity
Specific function:: Its physiological role is not yet clear.
Gene Name:: ACYP1
Uniprot ID:: P07311
Molecular weight:: 11260.84

Enzyme Details

7. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Enzyme Details

8. Carboxylesterase 5A

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:: CES5A
Uniprot ID:: Q6NT32
Molecular weight:: 63925.82

Showing Compound Card for Benzoic acid (CDB004927)

Structure for CDB004927 (Benzoic acid)

Enzymes