Metabolism / Metabolites
In rabbits, p-chlorobenzoyl-β-D-glucuronic acid is produced. /From Table/ In humans, p-chlorohippuric acid is produced. /From Table/ *Pseudomonas* WR912 was isolated by a three-step sequential enrichment culture using 3-chlorobenzoic acid, 4-chlorobenzoic acid, and finally 3,5-dichlorobenzoic acid as the sole carbon and energy sources. The doubling times of pure cultures under these growth substrates were 2.6, 3.3, and 5.2 h, respectively. During growth, chloride ions were eliminated stoichiometrically. The oxygen uptake rate of chlorobenzoates indicated low stereoselectivity of the initial benzoic acid 1,2-dioxygenation reaction. The activities of dihydrodihydroxybenzoic acid dehydrogenase, catechol 1,2-dioxygenase, and mucoconic acid cyclic isomerase were detected in the cell-free extract. The activity of ortho-catechin cleavage appears to involve the induction of isoenzymes with different stereoselectivity for p-chlorocatechins. Based on the similarity to the catabolism of chlorophenoxyacetic acid, a catabolism pathway for chlorocatechins was proposed. Chlorobenzoic acid-induced co-metabolism of 3,5-dimethylbenzoic acid in cells yielded 2,5-dihydro-2,4-dimethyl-5-oxofuran-2-acetic acid. A mixed microbial community enriched from sewage sludge inoculum and established in a specific culture medium was able to completely mineralize 4-chlorobenzoic acid. A microorganism identified as *Arthrobacter* sp. was isolated from this community and confirmed to utilize 4-chlorobenzoic acid as its sole carbon and energy source in pure culture. This microorganism (strain TM-1) uses the dehalogenation reaction of 4-chlorobenzoic acid as the initial step in its degradation pathway. The product, 4-hydroxybenzoic acid, is further metabolized by protocatechuic acid. Continuous culture and repeated subculturing improved the ability of strain TM-1 to degrade 4-chlorobenzoic acid in liquid medium at 25°C. Other chlorobenzoic acid esters and the parent compound benzoic acid could not support the growth of strain TM-1. An active cell extract was prepared and demonstrated to dehalogenate 4-chlorobenzoic acid, 4-fluorobenzoic acid, and 4-bromobenzoic acid. The optimal pH for dehalogenase activity was 6.8, and the optimal temperature was 20°C. Dissolved oxygen inhibited the activity, while manganese (Mn) promoted it. Strain modification increased the specific activity of the cell extract from 0.09 nmol/min for 4-hydroxybenzoic acid to 0.85 nmol/min for 4-hydroxybenzoic acid and shortened the doubling time of the strain from 50 hours to 1.6 hours.

Toxicity Summary
Identification and Uses: p-Chlorobenzoic acid is a white, odorless crystalline powder. It is used as a laboratory reagent and a raw material for chemical production. p-Chlorobenzoic acid is a degradation product of indomethacin. Human Exposure and Toxicity: No relevant human study data were found. Animal Studies: p-Chlorobenzoic acid is a potent inhibitor of 4-hydroxybenzoic acid:polyphenyltransferase in rat brain and liver mitochondria. After a single oral administration in animals, urisidase and histidine enzyme activities were detectable in serum within 8 hours of exposure, peaking within 15 hours and remaining stable within 25 hours. Enzyme activities then gradually decreased but did not return to control levels within 70 hours.

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Non-Human Toxicity Values
Oral LD50 in mice: 1170 mg/kg; Intraperitoneal LD50 in rats: 1000 mg/kg; Oral LD50 in rats: 1170 mg/kg

[1]. Efficiency of natural and engineered bacterial strains in the degradation of 4-chlorobenzoic acid in soil slurry[J]. International Biodeterioration & Biodegradation, 2009, 63(1): 112-115.

Triclinic crystals or a light, fluffy white powder. (NTP, 1992)
4-Chlorobenzoic acid is a monochlorobenzoic acid with a chlorine substituent at the 4-position. It is a bacterial xenobiotic metabolite. Its function is related to benzoic acid. It is the conjugate acid of 4-chlorobenzoic acid esters.
The given RN refers to the parent compound.

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Mechanism of Action
Caprylic acid, salicylic acid, valproic acid, p-octylbenzoic acid, p-nitrobenzoic acid, and p-chlorobenzoic acid all effectively inhibited the activation of benzoic acid to benzoyl-CoA by mitochondrial extracts. The inhibitory effect of p-aminobenzoic acid was much weaker. Among these compounds, only salicylic acid and p-nitrobenzoic acid could not be activated to the corresponding coenzyme A esters. Salicylic acid, p-chlorobenzoic acid, and p-nitrobenzoic acid effectively prevented the inhibitory effects of valproic acid, p-octylbenzoic acid, and p-aminobenzoic acid on glucose synthesis and α-keto[1-(14)C]isovalerate oxidation. p-Octylbenzoic acid and p-aminobenzoic acid significantly reduced the content of free coenzyme A and acetyl-CoA in hepatocytes and increased the content of acid-insoluble and acid-soluble coenzyme A esters, respectively. p-Chlorobenzoic acid and p-nitrobenzoic acid can prevent the chelation of coenzyme A to p-octylbenzoyl-CoA or p-aminobenzoyl-CoA in hepatocytes incubated with these compounds. p-Chlorobenzoic acid not only prevents but also reverses the inhibition of gluconeogenesis in hepatocytes incubated with p-octylbenzoic acid. These results suggest that p-chlorobenzoic acid or p-nitrobenzoic acid may effectively reverse some of the hepatotoxic effects of coenzyme A valproate or naturally occurring organic acids (e.g., organic acids that accumulate in Reye's syndrome or organic acidemia).

C7H5CLO2

156.57

155.998

74-11-3

15516-76-4 (mercury(+2)[2:1] salt) ; 3686-66-6 (hydrochloride salt)

6318

Typically exists as solids at room temperature

469 °F (NTP, 1992) ; 243 °C ; MP: 44 °C /p-Chlorobenzoic acid, methyl ester/ ; 243 °C

1

1

10

128

0

C1=CC(=CC=C1C(=O)O)Cl

XRHGYUZYPHTUJZ-UHFFFAOYSA-N

InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

4-chlorobenzoic acid

500g of 4-chlorobenzoic acid (standard)

2934.99.9001

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)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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