Relevant Data

Food Additives Approved in the United States

Flavouring Substances Approved by European Union:

  • Benzoic acid [show]

Food Additives Approved by WHO:


General Information

Chemical nameBenzoic acid
E No.E 210
INS.210
CAS number65-85-0
GroupNo
Component of the group Sorbic acid - sorbates; Benzoic acid - benzoates (E 200 - 213)
Sorbic acid - sorbates; Benzoic acid - benzoates; p-hydroxybenzoates (E 200 - 219)
Benzoic acid - benzoates (E 210 - 213)

From webgate.ec.europa.eu


Computed Descriptors

Download SDF
2D Structure
CID243
IUPAC Namebenzoic acid
InChIInChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChI KeyWPYMKLBDIGXBTP-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C=C1)C(=O)O
Molecular FormulaC7H6O2
Wikipediabenzoic acid

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight122.123
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity104.0
CACTVS Substructure Key Fingerprint A A A D c Y B g M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A C A m A A w C I A A A g C I A i D S C A A C A A A k A A A I i A E A C M g I J j K A F R C A c Q A k w A E I m Y e I y C C O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area37.3
Monoisotopic Mass122.037
Exact Mass122.037
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count9
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


Food Additives Biosynthesis/Degradation


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9557
Human Intestinal AbsorptionHIA+0.9886
Caco-2 PermeabilityCaco2+0.9187
P-glycoprotein SubstrateNon-substrate0.8494
P-glycoprotein InhibitorNon-inhibitor0.9914
Non-inhibitor0.9941
Renal Organic Cation TransporterNon-inhibitor0.9136
Distribution
Subcellular localizationMitochondria0.6419
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8003
CYP450 2D6 SubstrateNon-substrate0.9672
CYP450 3A4 SubstrateNon-substrate0.8374
CYP450 1A2 InhibitorNon-inhibitor0.8532
CYP450 2C9 InhibitorNon-inhibitor0.9861
CYP450 2D6 InhibitorNon-inhibitor0.9570
CYP450 2C19 InhibitorNon-inhibitor0.9878
CYP450 3A4 InhibitorNon-inhibitor0.9822
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9863
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9708
Non-inhibitor0.9882
AMES ToxicityNon AMES toxic0.9923
CarcinogensNon-carcinogens0.6024
Fish ToxicityHigh FHMT0.7212
Tetrahymena Pyriformis ToxicityHigh TPT0.8716
Honey Bee ToxicityHigh HBT0.7230
BiodegradationReady biodegradable0.8983
Acute Oral ToxicityIII0.8104
Carcinogenicity (Three-class)Non-required0.7497

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-1.5012LogS
Caco-2 Permeability1.8481LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7896LD50, mol/kg
Fish Toxicity2.5602pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.4980pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Temellini A, Mogavero S, Giulianotti PC, Pietrabissa A, Mosca F, Pacifici GM: Conjugation of benzoic acid with glycine in human liver and kidney: a study on the interindividual variability. Xenobiotica. 1993 Dec;23(12):1427-33.[8135043 ]
  2. Dix KJ, Coleman DP, Jeffcoat AR: Comparative metabolism and disposition of gemfibrozil in male and female Sprague-Dawley rats and Syrian golden hamsters. Drug Metab Dispos. 1999 Jan;27(1):138-46.[9884323 ]
  3. Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51.[2293213 ]
  4. Parry GE, Bunge AL, Silcox GD, Pershing LK, Pershing DW: Percutaneous absorption of benzoic acid across human skin. I. In vitro experiments and mathematical modeling. Pharm Res. 1990 Mar;7(3):230-6.[2339094 ]
  5. Nielsen NM, Bundgaard H: Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties. J Pharm Sci. 1988 Apr;77(4):285-98.[3379586 ]
  6. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79.[357810 ]
  7. Downard CD, Roberts LJ 2nd, Morrow JD: Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Clin Pharmacol Ther. 1995 Apr;57(4):441-5.[7712673 ]
  8. Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6.[2420162 ]
  9. Nacht S, Yeung D, Beasley JN Jr, Anjo MD, Maibach HI: Benzoyl peroxide: percutaneous penetration and metabolic disposition. J Am Acad Dermatol. 1981 Jan;4(1):31-7.[7204686 ]
  10. LeBel M, Ferron L, Masson M, Pichette J, Carrier C: Benzyl alcohol metabolism and elimination in neonates. Dev Pharmacol Ther. 1988;11(6):347-56.[3229281 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzoic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentBenzoic acids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzoic acid - Benzoyl - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound 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.

From ClassyFire


Targets

General Function:
Receptor binding
Specific Function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular Weight:
39473.75 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General Function:
Rna polymerase iii regulatory region dna binding
Specific Function:
Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling.
Gene Name:
PRDX5
Uniprot ID:
P30044
Molecular Weight:
22086.245 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Gtpase activity
Specific Function:
Involved in the transport of proteins between the endosomes and the trans Golgi network.
Gene Name:
RAB9A
Uniprot ID:
P51151
Molecular Weight:
22837.38 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Xenon atom binding
Specific Function:
Endoribonuclease responsible for the inhibition of the translation by cleaving mRNA. Inhibits cell-free protein synthesis. Cleaves phosphodiester bonds only in single-stranded RNA (By similarity).
Gene Name:
HRSP12
Uniprot ID:
P52758
Molecular Weight:
14493.53 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Transcription factor activity, bacterial-type rna polymerase core promoter proximal region sequence-specific binding
Specific Function:
Hydrogen peroxide sensor. Activates the expression of a regulon of hydrogen peroxide-inducible genes such as katG, gor, ahpC, ahpF, oxyS (a regulatory RNA), dps, fur and grxA. OxyR expression is negatively autoregulated by binding to a 43 bp region upstream of its own coding sequence. OxyR is inactivated by reduction of its essential disulfide bond by the product of GrxA, itself positively regulated by OxyR. Has also a positive regulatory effect on the production of surface proteins that control the colony morphology and auto-aggregation ability.
Gene Name:
oxyR
Uniprot ID:
P0ACQ4
Molecular Weight:
34275.59 Da
General Function:
Trisaccharide binding
Specific Function:
Positively regulates the transcription of the maltose regulon whose gene products are responsible for uptake and catabolism of malto-oligosaccharides. Binds and recognizes a DNA motif (called the malT box): 5'-GGA[TG]GA-3'.
Gene Name:
malT
Uniprot ID:
P06993
Molecular Weight:
103117.49 Da
General Function:
Intramolecular oxidoreductase activity, interconverting keto- and enol-groups
Specific Function:
Can use enol isomers of phenylpyruvate, 2-hydroxy-2,4-pentadienoate and (p-hydroxyphenyl)pyruvate as substrates.
Gene Name:
pptA
Uniprot ID:
P31992
Molecular Weight:
8672.84 Da
General Function:
Ferric iron binding
Gene Name:
clcA
Uniprot ID:
O67987
Molecular Weight:
28952.3 Da
General Function:
Hydrolase activity
Gene Name:
cumD
Uniprot ID:
P96965
Molecular Weight:
31489.385 Da
General Function:
Chloride peroxidase activity
Gene Name:
cpo
Uniprot ID:
O31168
Molecular Weight:
30354.465 Da
General Function:
Oxidoreductase activity
Specific Function:
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred.
Gene Name:
nfsB
Uniprot ID:
Q01234
Molecular Weight:
23949.98 Da
General Function:
Hydroxyquinol 1,2-dioxygenase activity
Specific Function:
Catalyzes the ortho-cleavage of the aromatic ring of hydroxyquinol.
Gene Name:
chqB
Uniprot ID:
Q5PXQ6
Molecular Weight:
31966.33 Da
General Function:
Dna-directed dna polymerase activity
Gene Name:
repA
Uniprot ID:
Q52546
Molecular Weight:
26728.84 Da
Specific Function:
The biological activity of the toxin is produced by the A chain, which activates intracellular adenyl cyclase.
Gene Name:
eltB
Uniprot ID:
P32890
Molecular Weight:
14133.255 Da
General Function:
Dipeptidyl-peptidase activity
Specific Function:
Hydrolyzes cocaine to benzoate and ecgonine methyl ester, endowing the bacteria with the ability to utilize cocaine as a sole source of carbon and energy for growth, as this bacterium lives in the rhizosphere of coca plants. Also efficiently hydrolyzes cocaethylene, a more potent cocaine metabolite that has been observed in patients who concurrently abuse cocaine and alcohol. Is able to prevent cocaine-induced convulsions and lethality in rat.
Gene Name:
cocE
Uniprot ID:
Q9L9D7
Molecular Weight:
62131.125 Da
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da

From T3DB