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Propanoic acid
Other names
Ethanecarboxylic acid
Identifiers
-3D images
Properties
74.08 g·mol-1
Appearance
Colorless liquid
Slightly rancid
0.98797 g/cm3
-20.5 °C (-4.9 °F; 252.7 K)
141.15 °C (286.07 °F; 414.30 K)
Sublimes at -48 °C
ΔsublHo = 74 kJ/mol
8.19 g/g (-28.3 °C)
34.97 g/g (-23.9 °C)
Miscible (≥ -19.3 °C)
Miscible in , ,
0.32 kPa (20 °C)
0.47 kPa (25 °C)
9.62 kPa (100 °C)
 (kH)
4.45·10-4 L·atm/mol
1.44·105 W/m·K
1.175 c (15 °C)
1.02 cP (25 °C)
0.668 cP (60 °C)
0.495 cP (90 °C)
a = 4.04 ?, b = 9.06 ?, c = 11 ?
α = 90°, β = 91.25°, γ = 90°
Thermochemistry
152.8 J/mol·K
191 J/mol·K
(ΔfHo298)
-510.8 kJ/mol
(ΔcHo298)
1527.3 kJ/mol
P280, P305+351+338, P310
54 °C (129 °F; 327 K)
512 °C (954 °F; 785 K)
1370 mg/kg (white mice, oral)
US health exposure limits ():
Related compounds
Related compounds
(εr), etc.
Thermodynamic
solid–liquid–gas
Except where noted otherwise, data is given for materials in their
(at 25 °C (77 °F), 100 kPa)
   (: /?)
Propionic acid (from the
words protos, meaning first, and pion, meaning fat; also known as propanoic acid) is a naturally occurring
3CH2COH. It is a clear liquid with a pungent and unpleasant smell somewhat resembling . The
CH3CH2COO- as well as the
of propionic acid are known as
(or propanoates).
Propionic acid was first described in 1844 by , who found it among the degradation products of . Over the next few years, other chemists produced propionic acid in various other ways, none of them realizing they were producing the same substance. In 1847, the French chemist
established all the acids to be the same compound, which he called propionic acid, from the
words protos, meaning first, and pion, meaning fat, because it is the smallest H(CH2)nCOOH acid that exhibits the properties of the other , such as producing an oily layer when salted out of water and having a
Propionic acid has physical properties intermediate between those of the smaller carboxylic acids,
acids, and the larger . It is miscible with water, but can be removed from water by adding salt. As with acetic and formic acids, it consists of
pairs of molecules as both the liquid and the vapor.
Propionic acid displays the general properties of carboxylic acids: It can form , , , and
derivatives. It can undergo alpha- with
in the presence of
(the ) to form CH3CHBrCOOH.
In industry, propionic acid is mainly produced by the hydrocarboxylation of
as the catalyst:
H2C=CH2 + H2O + CO → CH3CH2CO2H
It is also produced by the aerobic
of . In the presence of
, this reaction proceeds rapidly at temperatures as mild as 40–50 °C:
→ CH3CH2COOH.
Large amounts of propionic acid were once produced as a byproduct of acetic acid manufacture. At the current time, the world's largest producer of propionic acid is , with approximately 150 kt/a production capacity.
Propionic acid is produced biologically as its coenzyme A ester, , from the
breakdown of fatty acids containing
atoms, and also from the breakdown of some .
of the genus
produce propionic acid as the end-product of their
metabolism. This class of bacteria is commonly found in the stomachs of
and the , and their activity is partially responsible for the odor of both
It is also biosynthesized in the
of humans by bacterial
Propionic acid inhibits the growth of
at the levels between 0.1 and 1% by weight. As a result, most propionic acid produced is consumed as a
for both animal feed and food for human consumption. For animal feed, it is used either directly or as its
salt. The antibiotic
is added to cattle feed to favor propionibacteria over acetic acid pr this produces less carbon dioxide and feed conversion is better. This application accounts for about half of the world production of propionic acid. Another major application is as a preservative in baked goods, which use the
salts. As a , it is approved for use in the EU, USA and Australia and New Zealand. It is listed by its INS number (280) or
Propionic acid is also useful as an intermediate in the production of other chemicals, especially polymers. -acetate-propionate is a useful thermoplastic. Vinyl propionate is also used. In more specialized applications, it is also used to make
of propionic acid have fruit-like odors and are sometimes used as
or artificial flavorings.
The metabolism of propionic acid begins with its conversion to propionyl
(propionyl-CoA), the usual first step in the metabolism of . Since propionic acid has three carbons, propionyl-CoA cannot directly enter either
or the . In most , propionyl-CoA is
to D-methylmalonyl-CoA, which is
to L-methylmalonyl-CoA. A -dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to , which is an intermediate of the citric acid cycle and can be readily incorporated there.
In , a rare inherited genetic disorder, propionate acts as a metabolic toxin in liver cells by accumulating in mitochondria as propionyl-CoA and its derivative, methylcitrate, two tricarboxylic acid cycle inhibitors. Propanoate is metabolized oxidatively by , which suggests astrocytic vulnerability in propionic acidemia when intramitochondrial propionyl-CoA may accumulate. Propionic acidemia may alter both neuronal and glial gene expression by affecting histone acetylation. When propionic acid is infused directly into rodents' brains, it produces reversible behavior (e.g., , , social impairment, ) and brain changes (e.g., innate neuroinflammation, glutathione depletion) that may be used as a means to model
It also, being a three-carbon molecule, feeds into
(that is, the creation of
molecules from simpler molecules in the liver).
is host of several species of bacteria known as , which are named after their ability to produce propionic acid. The most notable one is the , which lives mainly in the
of the skin and is one of the principal causes of .
Lagowski, J.J., ed. (2012).
III. Elsevier. p. 362.  .
in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD.
(retrieved )
Seidell, A Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). D. Van Nostrand Company. p. 569.
, . Retrieved on .
Lide, David R., ed. (2009).
(90th ed.). : .  .
Strieter, F. J.; Templeton, D. H.; Scheuerman, R. F.; Sass, R. L. (1962). "The crystal structure of propionic acid". Acta Crystallographica 15 (12): 1233. :.
C. S. M V. du Vigneaud (1931). .
11: 20.; Coll. Vol. 2, p. 93
W. B M. R X. Sava (2005), "Carbonylation", , Weinheim: Wiley-VCH, :
den Besten, G; van Eunen, K; Groen, AK; Venema, K; Reijngoud, DJ; Bakker, BM (September 2013). "The role of short-chain fatty acids in the interplay between diet, gut microbiota, and host energy metabolism.". Journal of Lipid Research 54 (9): 2325–40. :.  .
. UK Food Standards Agency.
. US Food and Drug Administration.
. Australia New Zealand Food Standards Code. Comlaw.au.
D. F. MacF D. P. C K. Rodriguez-C A. E. F J. E. H F. B A. R. T M. K K.-P. Ossenkopp (2007). "Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders". Behavioral Brain Research 176 (1): 149–169. :.
N. H. T. N C. M S. Villa G F. R J. Storm-M V. G B. Hassel (2007). "Propionate increases neuronal histone acetylation, but is metabolized oxidatively by glia. Relevance for propionic acidemia". Journal of Neurochemistry 101 (3): 806–814. :.  .
Aschenbach, JR; Kristensen, NB; Donkin, SS; Hammon, HM; Penner, GB (December 2010). "Gluconeogenesis in dairy cows: the secret of making sweet milk from sour dough.". IUBMB Life 62 (12): 869–77. :.  .
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):545-51. doi: 10.6.. Epub
2012 Mar 1.Design, synthesis and preliminary activity evaluation of novel 3-amino-2-hydroxyl-3-phenylpropanoic acid derivatives as aminopeptidase N/CD13 inhibitors.1, , , , , , .1Department of Medicinal Chemistry, School of Pharmacy, Shan Dong University, Ji'nan, China.AbstractAminopeptidase N (APN/CD13) over expressed on tumour cells, plays a critical role in tumour invasion, metastasis and tumour angiogenesis. In this article, we described the design, synthesis and preliminary activity studies of novel 3-amino-2-hydroxyl-3-phenylpropanoic acid derivatives as APN inhibitors. The in vitro enzymatic inhibitions on APN from porcine kidney showed that compound 7e had the most potent inhibitory activity against APN with the IC(50) value to 1.26 ± 0.01 μM, which is better than that of bestatin (IC(50) = 2.55 ± 0.11 μM). In addition, compound 7e also showed better inhibitory activity against APN on human ovary clear cell carcinoma cell ES-2 than bestatin with the IC(50) value to 30.19 ± 1.02 μM versus 60.61 ± 0.1 μM. Compound 7e could be used as the lead compound in the future for anti-cancer agent research.PMID:
[PubMed - indexed for MEDLINE]
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