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Chemistry

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Also known as: 74-11-3, P-chlorobenzoic acid, Benzoic acid, 4-chloro-, Chlorodracylic acid, P-chlorbenzoic acid, Benzoic acid, p-chloro-
Molecular Formula
C7H5ClO2
Molecular Weight
156.56  g/mol
InChI Key
XRHGYUZYPHTUJZ-UHFFFAOYSA-N
FDA UNII
IC7888DF4L

4-Chlorobenzoic Acid
1 2D Structure

4-Chlorobenzoic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-chlorobenzoic acid
2.1.2 InChI
InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
2.1.3 InChI Key
XRHGYUZYPHTUJZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1C(=O)O)Cl
2.2 Other Identifiers
2.2.1 UNII
IC7888DF4L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-chlorobenzoate

2. 4-chlorobenzoic Acid, Calcium(2:1) Salt

3. 4-chlorobenzoic Acid, Mercury(+1) Salt

4. 4-chlorobenzoic Acid, Mercury(+2)(2:1) Salt

5. 4-chlorobenzoic Acid, Sodium Salt

6. 4-chlorobenzoic Acid, Sodium Salt, 11c-labeled

7. Para-chlorobenzoic Acid

2.3.2 Depositor-Supplied Synonyms

1. 74-11-3

2. P-chlorobenzoic Acid

3. Benzoic Acid, 4-chloro-

4. Chlorodracylic Acid

5. P-chlorbenzoic Acid

6. Benzoic Acid, P-chloro-

7. Para-chlorobenzoic Acid

8. 4-chloro-benzoic Acid

9. P-carboxychlorobenzene

10. Acido P-clorobenzoico

11. Acido P-clorobenzoico [italian]

12. Mfcd00002531

13. 4-chloro Benzoic Acid

14. Ic7888df4l

15. Chebi:30747

16. Nsc-32738

17. Ncgc00090858-02

18. Ccris 5994

19. Hsdb 6019

20. Einecs 200-805-9

21. Nsc 32738

22. Brn 0907196

23. Unii-ic7888df4l

24. Ai3-03715

25. Acemetacin Impurity A

26. Dsstox_cid_4772

27. 2-chloro-5-carboxybenzene

28. Bmse000438

29. Chembl618

30. Dsstox_rid_77525

31. Nciopen2_004782

32. Dsstox_gsid_24772

33. Schembl28384

34. 4-chlorobenzoic Acid, 99%

35. 4-09-00-00973 (beilstein Handbook Reference)

36. Mls002152923

37. Chlorobenzoic Acid, P-

38. Indomethacin Related Compound B

39. 4-chlorobenzoic Acid-[13c6]

40. Dtxsid9024772

41. Nsc8444

42. P-chlorobenzoic Acid [mi]

43. Zinc156865

44. Cs-m3680

45. Nsc-8444

46. Nsc32738

47. P-chlorobenzoic Acid [hsdb]

48. Str00110

49. Tox21_400062

50. Bdbm50405318

51. Stl164311

52. Akos000118962

53. P-chlorobenzoic Acid [who-dd]

54. Db03728

55. Ps-4074

56. Cas-74-11-3

57. Ncgc00090858-01

58. Ncgc00090858-03

59. 4-chlorobenzoic Acid, Analytical Standard

60. Smr001224523

61. Sy002326

62. Acemetacin Impurity A [ep Impurity]

63. Db-055838

64. Ft-0618183

65. Indometacin Impurity A [ep Impurity]

66. C02370

67. D77513

68. Indomethacin Related Compound B [usp-rs]

69. Ae-562/40168810

70. Q2235989

71. Sr-01000855009-2

72. W-104433

73. 4-chlorobenzoic Acid, Vetec(tm) Reagent Grade, 98%

74. F2191-0096

75. Z1258943359

76. Acemetacin Impurity A, European Pharmacopoeia (ep) Reference Standard

77. Indomethacin Related Compound B, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 156.56 g/mol
Molecular Formula C7H5ClO2
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass155.9978071 g/mol
Monoisotopic Mass155.9978071 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count10
Formal Charge0
Complexity128
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

P-chlorobenzoyl-beta-d-glucuronic acid in rabbit. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-19


Yields p-chlorohippuric acid in man. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-19


Pseudomonas sp. WR912 was isolated by continuous enrichment in three steps with 3-chloro-, 4-chloro-, and finally 3,5-dichlorobenzoate as sole source of carbon and energy. The doubling times of the pure culture with these growth substrates were 2.6, 3.3, and 5.2 h, respectively. Stoichiometric amounts of chloride were eliminated during growth. Oxygen uptake rates with chlorinated benzoates revealed low stereospecificity of the initial benzoate 1,2-dioxygenation. Dihydrodi-hydroxybenzoate dehydrogenase, catechol 1,2-dixoygenase, and muconate cycloisomerase activities were found in cell-free extracts. The ortho cleavage activity for catechols appeared to involve induction of isoenzymes with different stereospecificity towards chlorocatechols. A catabolic pathway for chlorocatechols was proposed on the basis of similarity to chlorophenoxyacetate catabolism, and cometabolism of 3,5-dimethylbenzoate by chlorobenzoate-induced cells yielded 2,5-dihydro-2,4-dimethyl-5-oxo-furan-2-acetic acid.

PMID:453823 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC243232 Hartmann J et al; Appl Environ Microbiol 37 (3): 421-8 (1979)


A mixed population, enriched and established in a defined medium, from a sewage sludge inoculum was capable of complete mineralization of 4-chlorobenzoate. An organism, identified as Arthrobacter sp., was isolated from the consortium and shown to be capable of utilizing 4-chlorobenzoate as the sole carbon and energy source in pure culture. This organism (strain TM-1), dehalogenated 4-chlorobenzoate as the initial step in the degradative pathway. The product, 4-hydroxybenzoate, was further metabolized via protocatechuate. The ability of strain TM-1 to degrade 4-chlorobenzoate in liquid medium at 25 C was improved by the use of continuous culture and repeated sequential subculturing. Other chlorinated benzoates and the parent compound benzoate did not support growth of strain TM-1. An active cell extract was prepared and shown to dehalogenate 4-chloro-, 4-fluoro-, and 4-bromobenzoate. Dehalogenase activity had an optimum pH of 6.8 and an optimum temperature of 20 C and was inhibited by dissolved oxygen and stimulated by manganese (Mn). Strain improvement resulted in an increase in the specific activity of the cell extract from 0.09 to 0.85 nmol of 4-hydroxybenzoate per min per mg of protein and a decrease in the doubling time of the organism from 50 to 1.6 hr.

PMID:16346660 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC241668 Marks TS et al; Appl Environ Microbiol 48 (5): 1020-5 (1984)


4.2 Mechanism of Action

Octanoate, salicylate, valproic acid, p-octyl-, p-nitro-, and p-chlorobenzoic acids were effective inhibitors of benzoic acid activation to benzoyl-CoA by mitochondrial extracts. p-Aminobenzoic acid was much less effective. Of these compounds, only salicylate and p-nitrobenzoic acid were not activated to their respective CoA esters. Salicylate, p-chloro- and p-nitrobenzoic acids effectively prevented inhibition of glucose synthesis and alpha-keto[1-(14)C]isovalerate oxidation by valproic acid, p-octyl-, and p-aminobenzoic acids, p-Octyl- and p-aminobenzoic acids greatly depleted hepatocyte free CoA and acetyl-CoA contents and increased the content of acid-insoluble and acid-soluble CoA esters respectively. p-Chloro- and p-nitrobenzoic acids prevented the sequestration of CoA as p-octylbenzoyl-CoA or p-aminobenzoyl-CoA in hepatocytes incubated with these compounds. p-Chlorobenzoic acid not only prevented but also reversed the inhibition of gluconeogenesis in hepatocytes incubated with p-octylbenzoic acid. These results suggest that p-chloro- or p-nitrobenzoic acids might be effectively used to reverse some of the hepatotoxic effects of the CoA esters of valproic acid or naturally-occurring organic acids, such as those which accumulate in Reye's Syndrome or organic acidemias.

PMID:3117062 Swartzentruber MS, Harris RA; Biochem Pharmacol 36 (19): 3147-53 (1987)


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ABOUT THIS PAGE

4-Chlorobenzoic Acid Manufacturers

A 4-Chlorobenzoic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of 4-Chlorobenzoic Acid, including repackagers and relabelers. The FDA regulates 4-Chlorobenzoic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. 4-Chlorobenzoic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

4-Chlorobenzoic Acid Suppliers

A 4-Chlorobenzoic Acid supplier is an individual or a company that provides 4-Chlorobenzoic Acid active pharmaceutical ingredient (API) or 4-Chlorobenzoic Acid finished formulations upon request. The 4-Chlorobenzoic Acid suppliers may include 4-Chlorobenzoic Acid API manufacturers, exporters, distributors and traders.

4-Chlorobenzoic Acid GMP

4-Chlorobenzoic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of 4-Chlorobenzoic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right 4-Chlorobenzoic Acid GMP manufacturer or 4-Chlorobenzoic Acid GMP API supplier for your needs.

4-Chlorobenzoic Acid CoA

A 4-Chlorobenzoic Acid CoA (Certificate of Analysis) is a formal document that attests to 4-Chlorobenzoic Acid's compliance with 4-Chlorobenzoic Acid specifications and serves as a tool for batch-level quality control.

4-Chlorobenzoic Acid CoA mostly includes findings from lab analyses of a specific batch. For each 4-Chlorobenzoic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

4-Chlorobenzoic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (4-Chlorobenzoic Acid EP), 4-Chlorobenzoic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (4-Chlorobenzoic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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