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
After oral ingestion of benzoic acid and sodium benzoate, there is a rapid absorption (of undissociated benzoic acid) from the gastrointestinal tract in experimental animals or humans. ... 100% absorption can be assumed. In humans, the peak plasma concentration is reached within 1-2 hr.
Experiments on the distribution and elimination of (14)C-benzoate in the rat have shown 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 conjugated with glycine in the liver. The resulting hippuric acid is excreted in the urine rapidly (75% to 100% of the dose is excreted within 6 hours; the remaining dose is excreted within 2 to 3 days).
/Investigators/ reported that 42.6% +/-16.5% of a dermally applied (14)C-Benzoic acid dose (4 ug/sq cm; in acetone) was excreted in the urine within 24 hours. When applied in petrolatum, 60.5% of the dose was absorbed.
For more Absorption, Distribution and Excretion (Complete) data for BENZOIC ACID (17 total), please visit the HSDB record page.

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Metabolism / Metabolites
Benzoic acid ... conjugated with glycine to give hippuric acid in ... many mammals (man, monkeys, pig, rabbit, rodents, cat, dog, ferret & hedgehog). Dog, ferret, & hedgehog also excreted ... benzoyl glucuronide ... but indian fruit bat excreted almost all dose as benzoyl glucuronide.
/Investigators/ demonstrated that biotransformation of benzoic acid to hippuric acid follows saturable or Michaelis-Menten kinetics in humans following ingestion of sodium benzoate. /Sodium Benzoate/
The availability of glycine was the rate-limiting factor in the formation of hippuric acid. When insufficient glycine was available benzoyl glucuronide was formed.
/Investigators/ reported that both lipoic acid and valproic acid reduced the clearance of benzoic acid in rats that had been "loaded" with glycine. Both acids reduced the availability of hepatic coenzyme A that is needed for the adenosine triphosphate (ATP)-dependent conjugation with glycine.
For more Metabolism/Metabolites (Complete) data for BENZOIC ACID (11 total), please visit the HSDB record page.
Benzoic acid has known human metabolites that include Benzoyl glucuronide.

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

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Interactions
The metabolism of the benzoates depletes glycine concentrations and can therefore alter the glycine-dependent metabolism of other compounds. /Investigators/ demonstrated that benzoic acid or sodium benzoate successfully competed with aspirin for glycine, resulting in increased concentration and persistence of salicylic acid in the body. Almost total inhibition of salicyluric acid formation in humans was achieved using either 2.7 g benzoic acid or 3.2 g sodium benzoate.
In rat liver microsomes deferoxamine was a potent inhibitor of the oxidation of the scavenging agent, benzoate. Nearly complete inhibition was observed at 33-100 uM.
Groups of 25 male and 25 female mice were given benzoic acid at a dose of 40 mg/kg bw/day, sodium bisulfite at 80 mg/kg bw/day, or a mixture of the two for 17 months. Mortality was greater in the groups receiving the mixture (62%) than in those receiving the individual substances (32%) at eight months.
Wistar rats /were administered/ 40 mg benzoic acid/kg/day and 80 mg sodium bisulphite/kg/day once daily /for/ 72 weeks. 50 rats /with/ initial body weight /of/ 100-120g /experienced/ reduced weight gain, kidney function and reaction on stress factors were altered (no further information), /and/ the erythrocyte sedimentation rate was increased.

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Non-Human Toxicity Values
LD50 Cat oral 2000 mg/kg
LD50 Dog oral 2000 mg/kg
LD50 Mouse intraperitoneal 1460 mg/kg
LD50 Mouse oral 1940 mg/kg
For more Non-Human Toxicity Values (Complete) data for BENZOIC ACID (7 total), please visit the HSDB record page.

[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 appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses.
Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate.
A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.
Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity.
Benzoic Acid has been reported in Desmos chinensis, Paeonia emodi, and other organisms with data available.
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. It often is conjugated 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 gut bacteria process polyphenols (from ingested fruits or beverages).
A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.
See also: Salicylic Acid (active moiety of); Benzoyl Peroxide (active moiety of); Sodium Benzoate (active moiety of) ... View More ...

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Therapeutic Uses
Antifungal Agents; Food Preservatives
Benzoic acid ... has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield's ointment (benzoic acid 6% and salicylic acid 3%).
... It is used especially in the treatment of athlete's foot and to lesser extent for management of ringworm.
Medication (vet): has been used with salicylic acid as topical antifungal
/Experimental Ther:/ Process for controlling waste nitrogen accumulation diseases in humans by administering at least 1 compound selected from group of benzoic acid, phenylacetic acid and their salts is disclosed. Sodium benzoate, (6.2 g/day) given to female patient with carbophosphate synthetase deficiency Increased total urinary nitrogen excretion 58%.

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.)