BENZOIC ACID
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
Food Additives Approved by European Union:
General Information
Synonyms: | BENZENECARBOXYLIC ACID, CARBOXYBENZENE, DRACYLIC ACID, PHENYL FORMIC ACID |
Chemical Names: | BENZOIC ACID |
CAS number: | 65-85-0 |
COE number: | 21 |
JECFA number: | 850 |
FEMA number: | 2131 |
INS: | 210 |
Functional Class: |
Food Additives PRESERVATIVE |
From apps.who.int
Evaluations
Evaluation year: | 2002 |
ADI: | 0-5 mg/kg bw (1996) |
Meeting: | 46 |
Specs Code: | R |
Comments: | No safety concern at current levels of intake when used as a flavouring agent (2002) |
Report: | TRS 913-JECFA 59/112 |
Tox Monograph: | FAS 48-JECFA 57/227 (2001) |
Specification: | COMPENDIUM ADDENDUM 12/FNP 52 Add. 12/67 (METALS LIMITS) (2004); FAO JECFA Monographs 1 vol.1/147 |
From apps.who.int
GSFA Provisions for BENZOIC ACID
Number | Food Category | Max Level | Notes |
---|---|---|---|
14.2.7 | Aromatized alcoholic beverages (e.g. beer, wine and spirituous cooler-type beverages, low alcoholic refreshers) |
1,000 mg/kg | Note 13 |
07.0 | Bakery wares |
1,000 mg/kg | Note 13 |
04.1.2.7 | Candied fruit |
1,000 mg/kg | Note 13 |
06.5 | Cereal and starch based desserts (e.g. rice pudding, tapioca pudding) |
1,000 mg/kg | Note 13 |
05.3 | Chewing gum |
1,500 mg/kg | Note 13 |
14.2.2 | Cider and perry |
1,000 mg/kg | Note 124,Note 13 |
05.1.3 | Cocoa-based spreads, including fillings |
1,500 mg/kg | Note XS86,Note 13 |
14.1.5 | Coffee, coffee substitutes, tea, herbal infusions, and other hot cereal and grain beverages, excluding cocoa |
1,000 mg/kg | Note 13 |
14.1.2.3 | Concentrates for fruit juice |
1,000 mg/kg | Note 122,Note 91,Note 13,Note 127 |
14.1.3.3 | Concentrates for fruit nectar |
1,000 mg/kg | Note 122,Note 91,Note 13,Note 127 |
14.1.3.4 | Concentrates for vegetable nectar |
600 mg/kg | Note 13 |
05.2 | Confectionery including hard and soft candy, nougats, etc. other than food categories 05.1, 05.3 and 05.4 |
1,500 mg/kg | Note 13,Note XS309R |
04.1.2.12 | Cooked fruit |
1,000 mg/kg | Note 13 |
09.2.4.2 | Cooked mollusks, crustaceans, and echinoderms |
2,000 mg/kg | Note 13,Note 82 |
04.2.2.8 | Cooked or fried vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), and seaweeds |
1,000 mg/kg | Note 13 |
08.3.1.2 | Cured (including salted) and dried non-heat treated processed comminuted meat, poultry, and game products |
1,000 mg/kg | Note 3,Note 13 |
08.2.1.2 | Cured (including salted) and dried non-heat treated processed meat, poultry, and game products in whole pieces or cuts |
1,000 mg/kg | Note 3,Note 13 |
01.7 | Dairy-based desserts (e.g. pudding, fruit or flavoured yoghurt) |
300 mg/kg | Note 13 |
05.4 | Decorations (e.g. for fine bakery wares), toppings (non-fruit) and sweet sauces |
1,500 mg/kg | Note 13 |
13.5 | Dietetic foods (e.g. supplementary foods for dietary use) excluding products of food categories 13.1 - 13.4 and 13.6 |
2,000 mg/kg | Note 13 |
13.3 | Dietetic foods intended for special medical purposes (excluding products of food category 13.1) |
1,500 mg/kg | Note 13 |
13.4 | Dietetic formulae for slimming purposes and weight reduction |
1,500 mg/kg | Note 13 |
04.1.2.2 | Dried fruit |
800 mg/kg | Note 13 |
04.2.2.2 | Dried vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), seaweeds, and nuts and seeds |
1,000 mg/kg | Note 13 |
10.4 | Egg-based desserts (e.g. custard) |
1,000 mg/kg | Note 13 |
02.3 | Fat emulsions mainly of type oil-in-water, including mixed and/or flavoured products based on fat emulsions |
1,000 mg/kg | Note 13 |
02.2.2 | Fat spreads, dairy fat spreads and blended spreads |
1,000 mg/kg | Note 13 |
02.4 | Fat-based desserts excluding dairy-based dessert products of food category 01.7 |
1,000 mg/kg | Note 13 |
04.1.2.10 | Fermented fruit products |
1,000 mg/kg | Note 13 |
04.2.2.7 | Fermented vegetable (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera) and seaweed products, excluding fermented soybean products of food categories 06.8.6, 06.8.7, 12.9.1, 12.9.2.1 and 12.9.2.3 |
1,000 mg/kg | Note 13 |
13.6 | Food supplements |
2,000 mg/kg | Note 13 |
04.1.2.11 | Fruit fillings for pastries |
1,000 mg/kg | Note 13 |
04.1.2.3 | Fruit in vinegar, oil, or brine |
1,000 mg/kg | Note 13 |
14.1.2.1 | Fruit juice |
1,000 mg/kg | Note 122,Note 91,Note 13 |
14.1.3.1 | Fruit nectar |
1,000 mg/kg | Note 122,Note 91,Note 13 |
04.1.2.8 | Fruit preparations, including pulp, purees, fruit toppings and coconut milk |
1,000 mg/kg | Note 13 |
04.1.2.9 | Fruit-based desserts, including fruit-flavoured water-based desserts |
1,000 mg/kg | Note 13 |
04.1.2.6 | Fruit-based spreads (e.g. chutney) excluding products of food category 04.1.2.5 |
1,000 mg/kg | Note 13 |
05.1.5 | Imitation chocolate, chocolate substitute products |
1,500 mg/kg | Note 13 |
04.1.2.5 | Jams, jellies, marmelades |
1,000 mg/kg | Note 13 |
10.2.1 | Liquid egg products |
5,000 mg/kg | Note 13 |
14.2.5 | Mead |
1,000 mg/kg | Note 13 |
12.4 | Mustards |
1,000 mg/kg | Note 13 |
11.4 | Other sugars and syrups (e.g. xylose, maple syrup, sugar toppings) |
1,000 mg/kg | Note 13 |
06.4.3 | Pre-cooked pastas and noodles and like products |
1,000 mg/kg | Note 13 |
12.7 | Salads (e.g. macaroni salad, potato salad) and sandwich spreads excluding cocoa- and nut-based spreads of food categories 04.2.2.5 and 05.1.3 |
1,500 mg/kg | Note 13 |
12.6 | Sauces and like products |
1,000 mg/kg | Note 13 |
12.2.2 | Seasonings and condiments |
1,000 mg/kg | Note 13 |
09.3 | Semi-preserved fish and fish products, including mollusks, crustaceans, and echinoderms |
2,000 mg/kg | Note 13,Note 120 |
09.2.5 | Smoked, dried, fermented, and/or salted fish and fish products, including mollusks, crustaceans, and echinoderms |
200 mg/kg | Note 121,Note 13 |
15.1 | Snacks - potato, cereal, flour or starch based (from roots and tubers, pulses and legumes) |
1,000 mg/kg | Note 13 |
12.5 | Soups and broths |
500 mg/kg | Note 339,Note 338,Note 13 |
11.6 | Table-top sweeteners, including those containing high-intensity sweeteners |
2,000 mg/kg | Note 13 |
04.2.2.6 | Vegetable (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), seaweed, and nut and seed pulps and preparations (e.g. vegetable desserts and sauces, candied vegetables) other than food category 04.2.2.5 |
3,000 mg/kg | Note 13 |
04.2.2.5 | Vegetable (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), seaweed, and nut and seed purees and spreads (e.g., peanut butter) |
1,000 mg/kg | Note 13 |
04.2.2.3 | Vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), and seaweeds in vinegar, oil, brine, or soybean sauce |
2,000 mg/kg | Note 13 |
12.3 | Vinegars |
1,000 mg/kg | Note 13 |
14.1.4 | Water-based flavoured drinks, including "sport," "energy," or "electrolyte" drinks and particulated drinks |
250 mg/kg | Note 13,Note 301 |
14.2.4 | Wines (other than grape) |
1,000 mg/kg | Note 13 |
From www.fao.org
Computed Descriptors
Download SDF2D Structure | |
CID | 243 |
IUPAC Name | benzoic acid |
InChI | InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) |
InChI Key | WPYMKLBDIGXBTP-UHFFFAOYSA-N |
Canonical SMILES | C1=CC=C(C=C1)C(=O)O |
Molecular Formula | C7H6O2 |
Wikipedia | benzoic acid |
From Pubchem
Computed Properties
Property Name | Property Value |
---|---|
Molecular Weight | 122.123 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 1 |
Complexity | 104.0 |
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 Area | 37.3 |
Monoisotopic Mass | 122.037 |
Exact Mass | 122.037 |
Compound Is Canonicalized | True |
Formal Charge | 0 |
Heavy Atom Count | 9 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9557 |
Human Intestinal Absorption | HIA+ | 0.9886 |
Caco-2 Permeability | Caco2+ | 0.9187 |
P-glycoprotein Substrate | Non-substrate | 0.8494 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9914 |
Non-inhibitor | 0.9941 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9136 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6419 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8003 |
CYP450 2D6 Substrate | Non-substrate | 0.9672 |
CYP450 3A4 Substrate | Non-substrate | 0.8374 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8532 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9861 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9570 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9878 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9822 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9863 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9708 |
Non-inhibitor | 0.9882 | |
AMES Toxicity | Non AMES toxic | 0.9923 |
Carcinogens | Non-carcinogens | 0.6024 |
Fish Toxicity | High FHMT | 0.7212 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.8716 |
Honey Bee Toxicity | High HBT | 0.7230 |
Biodegradation | Ready biodegradable | 0.8983 |
Acute Oral Toxicity | III | 0.8104 |
Carcinogenicity (Three-class) | Non-required | 0.7497 |
From admetSAR
ADMET Predicted Profile --- Regression
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.5012 | LogS |
Caco-2 Permeability | 1.8481 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.7896 | LD50, mol/kg |
Fish Toxicity | 2.5602 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.4980 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
Route of Exposure | None |
---|---|
Mechanism of Toxicity | None |
Metabolism | None |
Toxicity Values | None |
Lethal Dose | None |
Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
Minimum Risk Level | None |
Health Effects | None |
Treatment | None |
Reference |
|
From T3DB
Taxonomic Classification
Kingdom | Organic compounds |
---|---|
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Benzoic acids and derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Benzoic acids |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
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 |
Description | This 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
- 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
- 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
- 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
- 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
- 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