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Chemistry

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Also known as: Propanoic acid, 79-09-4, Ethylformic acid, Methylacetic acid, Carboxyethane, Metacetonic acid
Molecular Formula
C3H6O2
Molecular Weight
74.08  g/mol
InChI Key
XBDQKXXYIPTUBI-UHFFFAOYSA-N
FDA UNII
JHU490RVYR

Propionic Acid
propionic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Propionic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propanoic acid
2.1.2 InChI
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
2.1.3 InChI Key
XBDQKXXYIPTUBI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
JHU490RVYR
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chromium Propionate

2. Ethylformic Acid

3. Lithium Propanoate

4. Monoprop

5. Potassium Propionate

6. Propionic Acid, Zinc Salt

7. Zinc Propionate

2.3.2 Depositor-Supplied Synonyms

1. Propanoic Acid

2. 79-09-4

3. Ethylformic Acid

4. Methylacetic Acid

5. Carboxyethane

6. Metacetonic Acid

7. Ethanecarboxylic Acid

8. Pseudoacetic Acid

9. Luprosil

10. Monoprop

11. Propionate

12. Prozoin

13. Antischim B

14. Propionoic Acid

15. Acide Propionique

16. Methyl Acetic Acid

17. Sentry Grain Preserver

18. C3 Acid

19. Tenox P Grain Preservative

20. Caswell No. 707

21. Propionic Acid Grain Preserver

22. Fema No. 2924

23. Propionsaeure

24. Propcorn

25. Propkorn

26. Propoic Acid

27. Propioic Acid

28. Acide Propanoique

29. Propionic Acid (natural)

30. Kyselina Propionova

31. Carboxylic Acids, C1-5

32. Acide Propionique [french]

33. Kyselina Propionova [czech]

34. Ccris 6096

35. Proprionic Acid

36. C1-5 Carboxylic Acids

37. Epa Pesticide Chemical Code 077702

38. Fatty Acids, C3-24

39. Hsdb 1192

40. N-propionic Acid

41. Toxi-check

42. Ai3-04167

43. Ch3-ch2-cooh

44. Un1848

45. Brn 0506071

46. Propionic Acid [nf]

47. Chebi:30768

48. Jhu490rvyr

49. Chembl14021

50. Ins No.280

51. 68937-68-8

52. Ins-280

53. Metacetonate

54. Propanate

55. Pseudoacetate

56. Ethanecarboxylate

57. 68990-37-4

58. Propionic Acid (nf)

59. Propionic Acid [un1848] [corrosive]

60. E-280

61. Propionic Acid, >=99.5%

62. Propanyl Acid

63. Fema Number 2924

64. Einecs 201-176-3

65. Unii-jhu490rvyr

66. Mfcd00002756

67. Luprisol

68. Proponic Acid

69. 1-propanoic Acid

70. 2-methylacetic Acid

71. Einecs 273-079-4

72. Etco2h

73. Propionic Acid Solution

74. Propionic Acid, 99%

75. Propanoic Acid (9ci)

76. C2h5cooh

77. Dsstox_cid_5961

78. Bmse000179

79. Epitope Id:139981

80. Propionic Acid, >=99%

81. Propionic Acid, 99.5%

82. Ec 201-176-3

83. Propionic Acid [mi]

84. Dsstox_gsid_25961

85. Propionic Acid Reagent Grade

86. Natural Propionic Acid

87. Propionic Acid (6ci,8ci)

88. Propionic Acid [fcc]

89. 4-02-00-00695 (beilstein Handbook Reference)

90. Propionic Acid, 99%, Fcc

91. Propionic Acid [fhfi]

92. Propionic Acid [hsdb]

93. Propionic Acid [inci]

94. Propionic Acid [vandf]

95. Gtpl1062

96. Propionic Acid [mart.]

97. Dtxsid8025961

98. Propionic Acid [usp-rs]

99. Propionic Acid [who-dd]

100. Amy4114

101. Top Distillation Cut By-product Acids, Monobasic (c1-c5)

102. Methylacetic Acid, Propanoic Acid

103. Dtxsid001015846

104. Propionic Acid, Acs Reagent Grade

105. Carboxymethoxylaminehemihydrochloride

106. Propionic Acid, Analytical Standard

107. Zinc6050663

108. Propionic Acid, Natural, 99%, Fg

109. Tox21_304030

110. Bdbm50082199

111. Lmfa01010003

112. Stl168039

113. Propionic Acid, Feed Grade, 98.7%

114. Akos000118853

115. Db03766

116. Un 1848

117. Cas-79-09-4

118. Propionic Acid, For Synthesis, 99.5%

119. Ncgc00357239-01

120. Propionic Acid, >=99.5%, Fcc, Fg

121. Bp-20411

122. E280

123. Propionic Acid 100 Microg/ml In Ethanol

124. Propionic Acid, Acs Reagent, >=99.5%

125. Ft-0637136

126. Ft-0658557

127. P0500

128. Propionic Acid 100 Microg/ml In Cyclohexane

129. Propionic Acid, Saj First Grade, >=98.0%

130. C00163

131. D02310

132. Propionic Acid 1000 Microg/ml In Acetonitrile

133. Propionic Acid, Puriss. P.a., >=99.5% (gc)

134. Q422956

135. F2191-0098

136. Propionic Acid, Bioreagent, Suitable For Insect Cell Culture, ~99%

137. Propionic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 74.08 g/mol
Molecular Formula C3H6O2
XLogP30.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass74.036779430 g/mol
Monoisotopic Mass74.036779430 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count5
Formal Charge0
Complexity40.2
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

VET: Useful orally in ruminants as an antiketogenic agent ... it also stimulates rumen development in calves. /Propionic acid and salts/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 493


VET: ... As topical antifungal agents in various dermatoses.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 492


... Treating dermatophytic infections ... /Sodium Propionate/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 822


/VET:/ Propionic acid ... has been used to treat dermatomycoses. Propionic acid is also incorporated in manufactured animal feeds to help control fungal growth. At concentrations above 3 ug/ml it is fungicidal against a toxigenic strain of Aspergillus parasiticus.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 772


For more Therapeutic Uses (Complete) data for PROPIONIC ACID (8 total), please visit the HSDB record page.


4.2 Drug Warning

Both their low efficacy and exaggerated price make /propionic acid and sodium propionate/ irrational choices for treatment /of dermatomycoses/...

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1310


4.3 Drug Indication

Propanoic acid and various direct sodium or calcium salt formulations of the acid are currently most commonly approved and indicated by organizations like the FDA and EMA for use as an antibacterial food additive preservative in animal feed and food for human consumption. Similarly, although the use of propanoic acid or any of its direct sodium or calcium salt formulations as excipient ingredients in pharmaceuticals is not necessarily a major role for the compound today, sodium propionate was used in some vaginal cream preparations indicated for cervicitis, cervical tears, and/or postcauterization, postcryosurgery, and postconization of the cervix. In such products, the sodium propionate was primarily used to elicit a preservative, bacteriostatic effect while other active ingredients combined in the formulation like urea, benzalkonium chloride, inositol, and methionine and cystine amino acids facilitated debridement, enhanced medication spread, epithelialization promotion, and wound healing, respectively. Nevertheless, a great variety of propionic acid derivatives exist as separate pharmaceuticals, each with their own unique therapeutic categories, pharmacodynamics, and pharmacokinetics.


5 Pharmacology and Biochemistry
5.1 Pharmacology

As a naturally occurring carboxylic acid, propionic acid typically undergoes metabolism via conversion to propionyl coenzyme A (propionyl-CoA), which is part of the usual metabolic pathway that carboxylic acids participate within in the human body. Most of propionic acid's antibacterial and preservative activities subsequently stem from this metabolic pathway as the metabolic fate of propionates varies in different microorganisms, resulting in antimicrobial mechanisms of action that may revolve around differing propionate metabolites causing competition, inhibition, and/or interference effects along other metabolic pathways in the various microorganisms affected. In the human body, however, propionic acid is generally metabolized with little ill effect and ultimately becomes a chemical intermediate in the citric acid cycle.


5.2 Absorption, Distribution and Excretion

Absorption

Some propionic acid is oxidized to lactic acid during absorption, but most passes to the liver, which removes nearly all of it from the portal blood. Propionic acid represents 20-25% of absorbed volatile fatty acids. Propionic acid is rapidly absorbed through the gastrointestinal tract.


Route of Elimination

Most absorbed propionic acid is passed to the liver, which removes nearly all of it from the portal blood. Three days after a single oral administration of labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces.


Volume of Distribution

Three days after a single oral administration of labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces. The radioactivity found in skin, liver, intestine, and adipose tissue was 3.9, 1.1, 0.9, and 0.7%, respectively. Readily accessible data regarding the volume of distribution of propionic acid is not available.


Clearance

Readily accessible data regarding the clearance of propionic acid is not available.


Some propionic acid is oxidized to lactic acid during absorption but most passes to the liver, which removes nearly all of it from the portal blood ... propionic acid ... represents 20-25% of absorbed volatile fatty acids.

Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 736


Three days after a single oral admin of labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces. The radioactivity found in skin, liver, intestine, and adipose tissue was 3.9, 1.1, 0.9, and 0.7%, respectively.

KOZUKA H ET AL; EISEI KAGAKU 27 (5): 303-8 (1981)


Propionic acid is rapidly absorbed through the gastrointestinal tract and, even after large doses, very little is excreted in the urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:706


... In the forestomachs of rats fed 4% PA in powdered diet, the amount of PA in hyperplasias (1553 | 508 mug PA/g tissue) was three times higher than that in the remainder of the tissue (479 | 247 mug PA/g tissue). The PA content decreased progressively towards the glandular parts.

PMID:8473000 Bueld JE, Netter KJ; Food Chem Toxicol 31 (3): 169-176 (1993)


5.3 Metabolism/Metabolites

Propionic acid is first converted to propionyl coenzyme A (propionyl-CoA), however, it directly enter either beta oxidation or the citric acid cycles. As propionic acid has three carbons, propionyl-CoA. In the majority of vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is then isomerised to L-methylmalonyl-CoA. A vitamin B12-dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which can then be used as a substrate in the citric acid cycle.


Propionate is formed as the terminal three-carbon fragment (as propionyl-coenzyme A) in the oxidation of odd-number carbon fatty acids and from oxidation of the side chain of cholesterol. Radioactivity from propionate admin to fasting rats may appear in glycogen, glucose, citric acid cycle intermediates, amino acids, and proteins. The route of metabolism of propionic acid involves interaction with coenzyme A, carboxylation to form methylmalonyl-coenzyme A, and conversion to succinic acid, which enters the citric acid cycle. Propionic acid may be oxidized without forming ketone bodies and in contrast to acetic acid, is incorporated into a carbohydrate as well as lipid.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:706


The metab of radiolabeled sodium propionate was studied in rats three days after a single oral admin. Among the liver extracts, 89% of the liver radioactivity was found in trichloroacetic acid precipitated fraction, and 10% in glycogen.

KOZUKA H ET AL; EISEI KAGAKU 27 (5): 303-8 (1981)


Treatment with L-carnitine greatly enhanced the formation and excretion of short-chain acylcarnitines in three patients with propionic acidemia and in three normal controls. Mass spectrometry ... identified the acylcarnitine as propionylcarnitine in patients with propionic acidemia. The normal children excreted mostly acetylcarnitine. Propionic acidemia and other organic acidurias are characterized by the intramitochondrial accumulation of short-chain acyl-Coenzyme A (CoA) compounds. The substrate specificity of the carnitine acetyltransferase enzyme and its steady state nature appears to facilitate elimination of propionyl groups while restoring the acyl-acyl-Coenzyme A:free acyl-CoenzymeA ratio in the mitochondrion. L-carnitine may be a useful therapeutic approach for elimination of toxic acyl acyl-Coenzyme A compounds in several of these disorders.

PMID:6725560 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC437091 Roe CR et al; J Clin Invest 73 (6): 1785-8 (1984)


Propionic acid (10 mM) inhibited hepatocyte oxidation of 1-(14)C-pyruvate (10 mM) by 60%. This inhibition was not the result of substrate competition, as butyric acid had minimal effects on pyruvate oxidation. ... Propionic acid also inhibited oxidation of 1-(14)C palmitic acid (0.8 mM) by hepatocytes isolated from fed rats. ... These results demonstrate that propionic acid interferes with oxidative metabolism in intact hepatocytes.

PMID:3790065 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1146796 Brass EP et al; Biochem J 236 (1): 131-6 (1986)


For more Metabolism/Metabolites (Complete) data for PROPIONIC ACID (7 total), please visit the HSDB record page.


5.4 Biological Half-Life

The half-life of iv sodium propionate administered in the sheep animal model is about 6.9 +/- 0.4 minutes.


The t1/2 of the iv sodium propionate load ... from 6.9 +/- 0.4 min in the control sheep ... . /Sodium propionate/

PMID:4014846 Grohn Y et al; Am J Vet Res 46 (4): 952-8 (1985)


5.5 Mechanism of Action

The metabolic fate of propionates varies in different microorganisms. Some have enzyme systems that can convert succinate to propionyl-coenzyme A and through various further steps to propionate, CO2, or propionyl phoshpate. Still others can convert propionic acid to B-alanine or directly to CO2. Whatever the case, the inhibiting effect for microbials is likely related to competition with acetate in the acetokinase system, to the blockage of pyruvate conversion to acetyl-coenzyme A and to interference with B-alanine in pantothenic acid syntheses. Moreover, other studies suggest the antimicrobial activity of propionic acid revolves around its ability to reduce the pH of its immediate environment to levels of acidity that are harmful to pathogenic microbes as well as its ability to dissociate such that its lipid soluble undissociated form is capable of entering microbial cells. Additionally, there are also studies that suggest that propionic acid's antifungal activity may be the result of propionyl-CoA inhibiting glucose metabolism in certain species of fungus via the accumulation of the CoA-derivative.


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API | Excipient name

Propionic Acid

Synonyms

Propanoic acid, 79-09-4, Ethylformic acid, Methylacetic acid, Carboxyethane, Metacetonic acid

Cas Number

79-09-4

Unique Ingredient Identifier (UNII)

JHU490RVYR

About Propionic Acid

propionic acid is a metabolite found in or produced by Saccharomyces cerevisiae.

Propionic Acid Manufacturers

A Propionic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Propionic Acid, including repackagers and relabelers. The FDA regulates Propionic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Propionic 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.

click here to find a list of Propionic Acid manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Propionic Acid Suppliers

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

click here to find a list of Propionic Acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Propionic Acid GMP

Propionic 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 Propionic 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 Propionic Acid GMP manufacturer or Propionic Acid GMP API supplier for your needs.

Propionic Acid CoA

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

Propionic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Propionic 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.

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