Microbial Metabolite

OAT2-catalyzed efflux of glutamic acid and orotic acid from 293 cells expressing OAT2h is stimulated by benzoic acid (1 mM)[2].
Antibacterial activity of benzoic acid (0.5 and 2.0 mg/disc) against S. aureus, S. epidermidis, P. aeruginosa, and B. cereu) has been reported[4].

Combining thymol (HY-N6810) (100 mg/kg in diet, 1–14 days) with benzoic acid (2,000 mg/kg in diet) enhances growth performance, increases nutrient absorption and digestion, and lessens diarrhea in weaned pigs[3].

Absorption, Distribution and Excretion
Following oral administration of benzoic acid and sodium benzoate, they are rapidly absorbed (undissociated benzoic acid) from the gastrointestinal tract of experimental animals or humans. …Absorption can be considered to be 100%. In humans, peak plasma concentrations are reached within 1–2 hours. Distribution and elimination experiments of 14C-benzoate in rats showed no accumulation of sodium benzoate or benzoic acid in the body. Benzoic acid and sodium benzoate are rapidly absorbed from the gastrointestinal tract of mammals and bind to glycine in the liver. The resulting hippuric acid is rapidly excreted in the urine (75% to 100% of the dose is excreted within 6 hours; the remaining dose is excreted within 2 to 3 days). Researchers reported that 42.6% ± 16.5% of the dermatologically applied dose of (14)C-benzoic acid (4 μg/cm²; soluble in acetone) was excreted in the urine within 24 hours. When used in combination with petrolatum, 60.5% of the dose is absorbed. For more complete data on the absorption, distribution, and excretion of benzoic acids (17 in total), please visit the HSDB records page. Metabolites/Metabolites Benzoic acid…combines with glycine to form hippuric acid…in many mammals (humans, monkeys, pigs, rabbits, rodents, cats, dogs, ferrets, and hedgehogs). Dogs, ferrets, and hedgehogs also excrete…benzoyl glucuronide…but Indian fruit bats excrete almost all doses as benzoyl glucuronide. Researchers have demonstrated that the bioconversion of benzoic acid to hippuric acid after ingestion of sodium benzoate in humans follows saturated or Michaelis kinetics. Sodium benzoate. Glycine availability is the rate-limiting factor in hippuric acid formation. When glycine is insufficient, benzoyl glucuronide is formed. Researchers report that both lipoic acid and valproic acid can reduce the clearance of benzoic acid in rats already "loaded" with glycine. Both acids reduce the availability of coenzyme A in the liver, which is essential for the ATP-dependent binding of benzoic acid to glycine. For more complete data on the metabolism/metabolites of benzoic acid (11 metabolites in total), please visit the HSDB record page. Known human metabolites of benzoic acid include benzoyl glucuronide.

Toxicity Data
LC50 (Rat) => 26 mg/m³/1H

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[1]. Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. Int J Toxicol. 2001;20 Suppl 3:23-50.

[2]. Benzoic acid and specific 2-oxo acids activate hepatic efflux of glutamate at OAT2. Biochim Biophys Acta. 2013 Feb;1828(2):491-8.

[3]. Effects of benzoic Acid and thymol on growth performance and gut characteristics of weaned piglets. Asian-Australas J Anim Sci. 2015 Jun;28(6):827-39.

[4]. Simultaneous Determination of Benzoic Acid, Caffeic Acid and Chlorogenic Acid in Seeds of Eriobotrya japonica and their Antibacterial Effect.Journal of Applied Biological Chemistry. Volume 57 Issue 1. Pages.89-93 / 2014 / 1976-0442(pISSN) / 2234-7941(eISSN).

Benzoic acid is a white crystalline solid, slightly soluble in water. Its main hazard lies in the potential environmental damage it may cause upon release. Immediate measures should be taken to limit its spread into the environment. Benzoic acid can be used in the manufacture of other chemicals, as a food preservative, and for other purposes. Benzoic acid is a compound composed of a benzene ring core and carboxylic acid substituents. It has multiple functions, including as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonic acid 15-lipoxygenase) inhibitor, a plant metabolite, a human exogenous substance metabolite, an algal metabolite, and a drug allergen. It is the conjugate acid of benzoate. Benzoic acid is a widely used antimicrobial compound as a food preservative. It binds to glycine in the liver and is excreted as hippuric acid. Sodium benzoate, as its sodium salt form, can be used to treat urea cycle disorders because it can bind to amino acids. This leads to the excretion of amino acids, thereby lowering ammonia levels. Recent studies suggest that sodium benzoate (1 gram daily) may be effective as adjunctive therapy for schizophrenia. Compared to placebo, it reduced the total score on the Positive and Negative Syndrome Scale by 21%. Benzoic acid is a nitrogen-binding agent. Its mechanism of action is the binding of ammonium ions. Benzoic acid has been reported in chrysanthemum, peony, and other organisms with relevant data. Benzoic acid (C6H5COOH) is a colorless crystalline solid and the simplest aromatic carboxylic acid. It exists naturally in many plant and animal species in both free and benzoic acid ester forms. Most berries contain a significant amount of benzoic acid (approximately 0.05%). Cranberries contain up to 300-1300 mg of free benzoic acid per kilogram of fruit. Benzoic acid is an antibacterial compound widely used as a food preservative. It is normally bound to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when intestinal bacteria process polyphenols (from ingested fruits or beverages).
A widely used antibacterial compound as a food preservative. It binds to glycine in the liver and is excreted as hippuric acid.
See also: salicylic acid (active ingredient); benzoyl peroxide (active ingredient); sodium benzoate (active ingredient)...See more...

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Therapeutic Uses
Antifungal agent; food preservative
Benzoic acid...has long been used as an antifungal agent in topical treatments, such as Whitfield ointment (6% benzoic acid and 3% salicylic acid).
...It is used particularly for the treatment of athlete's foot, and secondarily for the treatment of tinea corporis.
Veterinary medicine: It has been used in combination with salicylic acid as a topical antifungal agent.
/Experimental therapy:/This invention discloses a method for controlling diseases of waste nitrogen accumulation in the human body by administering at least one compound selected from benzoic acid, phenylacetic acid, and their salts. Administration of sodium benzoate (6.2 g/day) to female patients with carbophosphate synthase deficiency resulted in a 58% increase in total urinary nitrogen excretion.

C7H6O2

122.12

122.036

C, 68.85; H, 4.95; O, 26.20

65-85-0

Benzoic acid lithium;553-54-8;Benzoic acid-d5;1079-02-3;Benzoic acid-13C6;125945-98-4;Benzoic-3,5 Acid-d2;37960-84-2;Benzoic acid-13C;3880-99-7

243

White to off-white solid powder

1.2±0.1 g/cm3

249.3±9.0 °C at 760 mmHg

121-125 °C(lit.)

121.1±0.0 °C

0.0±0.5 mmHg at 25°C

1.564

1.89

1

2

1

9

104

0

O([H])C(C1C([H])=C([H])C([H])=C([H])C=1[H])=O

WPYMKLBDIGXBTP-UHFFFAOYSA-N

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

benzoic acid

Benzoic acid; Benzoesaeure; Benzenecarboxylic acid; Benzeneformic acid;

2934.99.03.00

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : 24~100 mg/mL ( 196.52~818.87 mM )
H2O: ~7.14 mg/mL (~58.47 mM )
Ethanol : ~24 mg/mL

Solubility in Formulation 1: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (20.47 mM)

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Solubility in Formulation 5: 4.55 mg/mL (37.26 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

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 (Please use freshly prepared in vivo formulations for optimal results.)