Showing Compound Benzoic acid (FDB008739)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:13 UTC

Update date

2024-11-29 22:26:50 UTC

Primary ID

FDB008739

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Benzoic acid

Description

Widespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits.

CAS Number

65-85-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
E210	db_source
FEMA 2131	db_source

Predicted Properties

Property	Value	Source
Water Solubility	7.08 g/L	ALOGPS
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

Chemical Formula

C7H6O2

IUPAC name

benzoic acid

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

Isomeric SMILES

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

Average Molecular Weight

122.123

Monoisotopic Molecular Weight

122.036779433

Classification

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

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Asthma

Role

Environmental role:

Air pollutant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 68.85%; H 4.95%; O 26.20%	DFC
Melting Point	Mp 122°	DFC
Boiling Point	Bp10 133°	DFC
Experimental Water Solubility	3.4 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	1.87	HANSCH,C ET AL. (1995)
Experimental pKa	4.19
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	300 (E1%/1cm 46.8) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

427

DrugBank ID

DB03793

HMDB ID

HMDB01870

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

65-85-0

GoodScent ID

rw1033731

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

427

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

Descriptor	ID	Definition	Reference
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	DUKE
Anesthetic		A drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti otitic	52217	An agent that reduces inflammation and infection in the ear, commonly used to treat otitis media (middle ear infection) and other ear disorders, promoting hearing health and alleviating symptoms such as pain and discomfort.	DUKE
Anti pyretic	35493	An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.	DUKE
Anti-salmonella	33282	An agent that targets and eliminates Salmonella bacteria, reducing the risk of food poisoning and gastrointestinal infections. Therapeutically, it is used to treat salmonellosis, a disease caused by Salmonella infection, and to prevent outbreaks in high-risk individuals, such as those with weakened immune systems.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-yeast	33281	An agent that inhibits the growth of yeast, playing a role in preventing fungal infections. Therapeutically, it is used to treat conditions such as candidiasis and athlete's foot, and has applications in managing digestive issues and skin infections.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Expectorant	52217	An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.	DUKE
Name	48318	flavor	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phytoalexin	26115	A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.	DUKE
Tyrosinase inhibitor	59997	An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology.	DUKE
Uricosuric		A substance that increases uric acid excretion in the urine, reducing blood plasma concentration. It plays a biological role in preventing uric acid buildup. Therapeutically, it's used to treat gout and hyperuricemia, managing symptoms and preventing complications. Key medical uses include reducing uric acid levels and alleviating gout attacks.	DUKE
Vulnerary	73336	An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Liver carboxylesterase 1	CES1	P23141
Lysosomal acid lipase/cholesteryl ester hydrolase	LIPA	P38571
Carboxylesterase 5A	CES5A	Q6NT32
Cocaine esterase	CES2	O00748
Acylphosphatase-2	ACYP2	P14621
Acylphosphatase-1	ACYP1	P07311

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Hippuric Acid	SMP0123209	Not Available
Metabolism and Physiological Effects of 4-Hydroxyhippuric Acid	SMP0125537	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
urine	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.