Benzoic acid (YMDB02301)

Identification

YMDB ID

YMDB02301

Name

Benzoic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

65-85-0

Weight

Average: 122.1213
Monoisotopic: 122.036779436

InChI Key

WPYMKLBDIGXBTP-UHFFFAOYSA-N

InChI

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

IUPAC Name

benzoic acid

Traditional IUPAC Name

benzoic acid

Chemical Formula

C₇H₆O₂

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

122.4 °C

Experimental Properties

Property	Value	Reference
Water Solubility	3.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.87 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Balsam	FDB008739
Faint	FDB008739
Urine	FDB008739

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a70-0900000000-5284a0c1c77a1979e1f4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-056r-3900000000-1c74c32fa650fcd4cb4d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-6900000000-fa50606b2e84fc4cefe9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9600000000-d08dbc757a6de6c3f54e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0adi-9800000000-40f904bf20072c72a08b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pk9-9800000000-b93fc1120a1c74b88fa3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-5900000000-1b6bbf98557af374f3a5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0570-0900000000-ecd208f1e7b4d5ad85f2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a70-0900000000-5284a0c1c77a1979e1f4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-056r-3900000000-1c74c32fa650fcd4cb4d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a70-0900000000-cec9e1ab69521049d1e4	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-7900000000-5ad752bd6787261a11d0	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7900000000-1c4c0dbbb165ef614f43	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00b9-9500000000-f312a552bef1a2927e64	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9100000000-dafd91c9134bc4143743	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00b9-9400000000-29ca905567aa5c59d46b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positive	splash10-05i0-6900000000-fa50606b2e84fc4cefe9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a6r-9600000000-d08dbc757a6de6c3f54e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0adi-9800000000-2693809ae064e720bf58	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pk9-9800000000-2c6be5ecee1848091a24	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-4644ee08861e75d0b808	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00b9-9400000000-11baabb3c0bb283b1c6e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004l-9100000000-4875643627420279223b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-97a21f3206f5c1f0ba7e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-4644ee08861e75d0b808	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00b9-9400000000-11baabb3c0bb283b1c6e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004l-9100000000-4875643627420279223b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-97a21f3206f5c1f0ba7e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-0900000000-94c7f13620a367bf5516	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00di-0900000000-f060e7aa8085ec6be223	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00di-0900000000-a28fdef9c1c00d45c3ff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-0900000000-3cad9aa6b0980c87bcc3	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-ee9de948bfb30da0a400	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-1900000000-c18a9b04d65d91fdd99e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-9300000000-0878408a026788c942a0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-3900000000-f25040451834faf3bf91	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-9500000000-b352342b60fd48a0c127	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-1d11331d7d21e32dbdba	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0pk9-8900000000-3d79c70c455799ab33e3	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.

External Links:

Resource	Link
CHEBI ID	30746
HMDB ID	HMDB01870
Pubchem Compound ID	243
Kegg ID	C00180
ChemSpider ID	238
FOODB ID	FDB008739
Wikipedia ID	Benzoic_Acid
BioCyc ID	Not Available

Structure for #<Compound:0xb136c28c>