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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/14 22:44:33」(JST)

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Propionic acid (from the Greek words protos, meaning first, and pion, meaning fat; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH₃CH₂COOH. It is a clear liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH₃CH₂COO⁻ as well as the salts and esters of propionic acid are known as propionates (or propanoates).

History

Propionic acid was first described in 1844 by Johann Gottlieb, who found it among the degradation products of sugar. 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 Jean-Baptiste Dumas established all the acids to be the same compound, which he called propionic acid, from the Greek words protos, meaning first, and pion, meaning fat, because it is the smallest H(CH₂)_nCOOH acid that exhibits the properties of the other fatty acids, such as producing an oily layer when salted out of water and having a soapy potassium salt.

Properties

Propionic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acids, and the larger fatty acids. It is miscible with water, but can be removed from water by adding salt. As with acetic and formic acids, it consists of hydrogen bonded pairs of molecules as both the liquid and the vapor.

Propionic acid displays the general properties of carboxylic acids: It can form amide, ester, anhydride, and chloride derivatives. It can undergo alpha-halogenation with bromine in the presence of PBr₃ as catalyst (the HVZ reaction) to form CH₃CHBrCOOH.^[10]

Production

In industry, propionic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:^[11]

H₂C=CH₂ + H₂O + CO → CH₃CH₂CO₂H

It is also produced by the aerobic oxidation of propionaldehyde. In the presence of cobalt or manganese ions, this reaction proceeds rapidly at temperatures as mild as 40–50 °C:

CH₃CH₂CHO + ½ O₂ → 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 BASF, with approximately 150 kt/a production capacity.

Propionic acid is produced biologically as its coenzyme A ester, propionyl-CoA, from the metabolic breakdown of fatty acids containing odd numbers of carbon atoms, and also from the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propionic acid as the end-product of their anaerobic metabolism. This class of bacteria is commonly found in the stomachs of ruminants and the sweat glands of humans, and their activity is partially responsible for the odor of both Swiss cheese and sweat.

It is also biosynthesized in the large intestine of humans by bacterial fermentation of dietary fibre.^[12]

Industrial uses

Propionic acid inhibits the growth of mold and some bacteria at the levels between 0.1 and 1% by weight. As a result, most propionic acid produced is consumed as a preservative for both animal feed and food for human consumption. For animal feed, it is used either directly or as its ammonium salt. The antibiotic Monensin is added to cattle feed to favor propionibacteria over acetic acid producers in the rumen; 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 sodium and calcium salts.^[11] As a food additive, it is approved for use in the EU,^[13] USA^[14] and Australia and New Zealand.^[15] It is listed by its INS number (280) or E number E280.

Propionic acid is also useful as an intermediate in the production of other chemicals, especially polymers. Cellulose-acetate-propionate is a useful thermoplastic. Vinyl propionate is also used. In more specialized applications, it is also used to make pesticides and pharmaceuticals. The esters of propionic acid have fruit-like odors and are sometimes used as solvents or artificial flavorings.^[11]

Biological uses

The metabolism of propionic acid begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propionic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation or the citric acid cycles. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. A vitamin B12-dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which is an intermediate of the citric acid cycle and can be readily incorporated there.

In propionic acidemia, 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 glia, 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.^[16]^[17] When propionic acid is infused directly into rodents' brains, it produces reversible behavior (e.g., hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g., innate neuroinflammation, glutathione depletion) that may be used as a means to model autism in rats.^[16]

It also, being a three-carbon molecule, feeds into hepatic gluconeogenesis (that is, the creation of glucose molecules from simpler molecules in the liver).^[18]

Human occurrence

The human skin is host of several species of bacteria known as Propionibacteria, which are named after their ability to produce propionic acid. The most notable one is the Propionibacterium acnes, which lives mainly in the sebaceous glands of the skin and is one of the principal causes of acne.

References

^ ^a ^b ^c ^d ^e "NIOSH Pocket Guide to Chemical Hazards #0529". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d ^e Lagowski, J.J., ed. (2012). The Chemistry of Nonaqueous Solvents III. Elsevier. p. 362. ISBN 0323151035.
^ ^a ^b ^c ^d ^e ^f Propanoic acid 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. http://webbook.nist.gov (retrieved 2014-06-13)
^ Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). D. Van Nostrand Company. p. 569.
^ ^a ^b ^c http://chemister.ru/Database/properties-en.php?dbid=1&id=1485
^ ^a ^b ^c ^d ^e CID 1032 from PubChem
^ ^a ^b ^c ^d ^e Sigma-Aldrich Co., Propionic acid. Retrieved on 2014-06-13.
^ ^a ^b Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
^ ^a ^b ^c Strieter, F. J.; Templeton, D. H.; Scheuerman, R. F.; Sass, R. L. (1962). "The crystal structure of propionic acid". Acta Crystallographica 15 (12): 1233. doi:10.1107/S0365110X62003278. edit
^ C. S. Marvel; V. du Vigneaud (1931). "α-bromo-Isovaleric acid". Org. Synth. 11: 20. ; Coll. Vol. 2, p. 93
^ ^a ^b ^c W. Bertleff; M. Roeper; X. Sava (2005), "Carbonylation", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_217
^ 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. doi:10.1194/jlr.R036012. PMID 23821742.
^ "Current EU approved additives and their E Numbers". UK Food Standards Agency. Retrieved 2011-10-27.
^ "Listing of Food Additives Status Part II". US Food and Drug Administration. Retrieved 2011-10-27.
^ "Standard 1.2.4 - Labelling of ingredients". Australia New Zealand Food Standards Code. Comlaw.au. Retrieved 2011-10-27.
^ ^a ^b D. F. MacFabe; D. P. Cain; K. Rodriguez-Capote; A. E. Franklin; J. E. Hoffman; F. Boon; A. R. Taylor; M. Kavaliers; 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. doi:10.1016/j.bbr.2006.07.025.
^ N. H. T. Nguyen; C. Morland; S. Villa Gonzalez; F. Rise; J. Storm-Mathisen; V. Gundersen; 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. doi:10.1111/j.1471-4159.2006.04397.x. PMID 17286595.
^ 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. doi:10.1002/iub.400. PMID 21171012.

External links

NIST Standard Reference Database
International Chemical Safety Card 0806
NIOSH Pocket Guide to Chemical Hazards
Technical data of propionic acid of BASF
Neurobiological effects of intraventricular propionic acid in ratsPossible role of short chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders
The Propionic Acids. Gastrointestinal Toxicity in Various Species
Propionic Acid Technical Data Sheet

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English Journal

Two new compounds from the fungus Penicilliumcrustosum YN-HT-15.

Liu YP, Chen G, Wang HF, Zhang XL, Pei YH.Author information a School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Shenyang , 110016 , China.AbstractOur current natural product program researches the second metabolites of a fungus Penicilliumcrustosum YN-HT-15 isolated from the red soil (Yunnan Province, China), to discover potential antitumor chemical entities. Two new compounds were isolated from the ethyl acetate extract of the fermentation broth of the fungus, and their structures were characterized as 1-(2',4'-dihydroxy-5'-methyl-3'-methylsulfanylmethyl-phenyl)-ethanone (1) and R-3-(3'-acetyl-2',6'-dihydroxy-5'-methylphenyl)-2-methyl-propionic acid methyl ester (2) on the basis of spectroscopic data.
Journal of Asian natural products research.J Asian Nat Prod Res.2014 Mar;16(3):281-4. doi: 10.1080/10286020.2013.867851. Epub 2013 Dec 18.
Our current natural product program researches the second metabolites of a fungus Penicilliumcrustosum YN-HT-15 isolated from the red soil (Yunnan Province, China), to discover potential antitumor chemical entities. Two new compounds were isolated from the ethyl acetate extract of the fermentation b
PMID 24344736

Electrochemical immunosensor for the determination of insulin-like growth factor-1 using electrodes modified with carbon nanotubes-poly(pyrrole propionic acid) hybrids.

Serafín V, Agüí L, Yáñez-Sedeño P, Pingarrón JM.Author information Department of Analytical Chemistry, Faculty of Chemistry, University Complutense of Madrid, 28040 Madrid, Spain.AbstractAn amperometric immunosensor for the determination of the hormone insulin-like growth factor 1 (IGF1) is reported for the first time in this work. As electrochemical transducer, a multiwalled carbon nanotubes-modified glassy carbon electrode on which poly(pyrrole propionic acid) was electropolymerized was prepared. This approach provided a high content of surface confined carboxyl groups suitable for direct covalent binding of anti-IGF1 monoclonal antibody. A sandwich-type immunoassay using a polyclonal antibody labeled with peroxidase, hydrogen peroxide as the enzyme substrate and catechol as redox mediator was employed to monitor the affinity reaction. All the variables involved in the preparation of the modified electrode were optimized and the electrodes were characterized by electrochemical impedance spectroscopy and cyclic voltammetry. Moreover, the different experimental variables affecting the amperometric response of the immunosensor were also optimized. The calibration graph for IGF1 showed a range of linearity extending from 0.5 to 1000 pg/mL, with a detection limit, 0.25 pg/mL, more than 100 times lower than the lowest values reported for the ELISA immunoassays available for IGF1 (30 pg/mL, approximately). Excellent reproducibility for the measurements carried out with different immunosensors and selectivity against other hormones were also evidenced. A commercial human serum spiked with IGF1 at different levels between 0.01 and 10.0 ng/mL was analyzed with good results.
Biosensors & bioelectronics.Biosens Bioelectron.2014 Feb 15;52:98-104. doi: 10.1016/j.bios.2013.08.021. Epub 2013 Aug 29.
An amperometric immunosensor for the determination of the hormone insulin-like growth factor 1 (IGF1) is reported for the first time in this work. As electrochemical transducer, a multiwalled carbon nanotubes-modified glassy carbon electrode on which poly(pyrrole propionic acid) was electropolymeriz
PMID 24035852

Functional Screening and In Vitro Analysis Reveal Thioesterases with Enhanced Substrate Specificity Profiles That Improve Short-Chain Fatty Acid Production in Escherichia coli.

McMahon MD, Prather KL.Author information Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts, USA.AbstractShort-chain fatty acid (SCFA) biosynthesis is pertinent to production of biofuels, industrial compounds, and pharmaceuticals from renewable resources. To expand on Escherichia coli SCFA products, we previously implemented a coenzyme A (CoA)-dependent pathway that condenses acetyl-CoA to a diverse group of short-chain fatty acyl-CoAs. To increase product titers and reduce premature pathway termination products, we conducted in vivo and in vitro analyses to understand and improve the specificity of the acyl-CoA thioesterase enzyme, which releases fatty acids from CoA. A total of 62 putative bacterial thioesterases, including 23 from the cow rumen microbiome, were inserted into a pathway that condenses acetyl-CoA to an acyl-CoA molecule derived from exogenously provided propionic or isobutyric acid. Functional screening revealed thioesterases that increase production of saturated (valerate), unsaturated (trans-2-pentenoate), and branched (4-methylvalerate) SCFAs compared to overexpression of E. coli thioesterase tesB or native expression of endogenous thioesterases. To determine if altered thioesterase acyl-CoA substrate specificity caused the increase in product titers, six of the most promising enzymes were analyzed in vitro. Biochemical assays revealed that the most productive thioesterases rely on promiscuous activity but have greater specificity for product-associated acyl-CoAs than for precursor acyl-CoAs. In this study, we introduce novel thioesterases with improved specificity for saturated, branched, and unsaturated short-chain acyl-CoAs, thereby expanding the diversity of potential fatty acid products while increasing titers of current products. The growing uncertainty associated with protein database annotations denotes this study as a model for isolating functional biochemical pathway enzymes in situations where experimental evidence of enzyme function is absent.
Applied and environmental microbiology.Appl Environ Microbiol.2014 Feb;80(3):1042-50. doi: 10.1128/AEM.03303-13. Epub 2013 Nov 22.
Short-chain fatty acid (SCFA) biosynthesis is pertinent to production of biofuels, industrial compounds, and pharmaceuticals from renewable resources. To expand on Escherichia coli SCFA products, we previously implemented a coenzyme A (CoA)-dependent pathway that condenses acetyl-CoA to a diverse gr
PMID 24271180

Japanese Journal

Trehalose accumulation enhances tolerance of Saccharomyces cerevisiae to acetic acid

Yoshiyama Yoko,Tanaka Koichi,Yoshiyama Kohei [他]
Journal of bioscience and bioengineering 119(2), 172-175, 2015-02
NAID 40020370748

近赤外分光分析によるオオムギ（Hordeum vulgare L.）ホールクロップサイレージ新鮮物を用いた飼料成分および発酵品質の推定

江口研太郎,佐藤節郎
日本草地学会誌 60(4), 227-234, 2015
オオムギホールクロップサイレージ新鮮物（120点）を用いて近赤外分光分析で迅速に飼料成分および発酵品質を評価する技術を開発した。検量線の検定におけるR2v値とRPD値の結果は，乾物率（R2v = 0.93；RPD = 3.6），粗タンパク質含量（R2v = 0.86；RPD = 2.6），粗脂肪含量（R2v = 0.77；RPD = 1.8），ADFom含量（R2v = 0.85；RPD = 2. …
NAID 130005058940

3-13-2 炭素繊維担体を用いたメタン発酵の微生物群集構造解析(Session 3-13 発酵、乾燥等)

鈴木崇司,多田千佳
日本エネルギー学会大会講演要旨集 (23), 160-161, 2014-07-14
… By this means, accumulation of organic acids such as propionic acid fell and methane production improved. … Analysis of the microbial community structure in the reactor, revealed the presence of Anaerobaculum mibile, which participates in organic acid decomposition, and Coprothemobacter proteolyticus, which participates in protein decomposition. …
NAID 110009891899

Related Pictures

★リンクテーブル★

リンク元	「プロピオン酸」
拡張検索	「isoxazolepropionic acid」「β-aminopropionic acid」

「プロピオン酸」

Propanoic acid
Names
	IUPAC name Propanoic acid
	Other names Ethanecarboxylic acid
Identifiers
CAS Registry Number	79-09-4
ChEBI	CHEBI:30768
ChEMBL	ChEMBL14021
ChemSpider	1005
DrugBank	DB03766
	InChI InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) ; Key: XBDQKXXYIPTUBI-UHFFFAOYSA-N ;
IUPHAR/BPS	1062
Jmol-3D images	Image; Image
PubChem	1032
RTECS number	UE5950000
	SMILES CCC(=O)O ; CCC(=O)O ;
Properties
Chemical formula	C3H6O2
Molar mass	74.08 g·mol−1
Appearance	Colorless, oily liquid
Odor	Pungent, rancid, unpleasant
Density	0.98797 g/cm3
Melting point	−20.5 °C (−4.9 °F; 252.7 K)
Boiling point	141.15 °C (286.07 °F; 414.30 K)
Sublimation; conditions	Sublimes at −48 °C; ΔsublHo = 74 kJ/mol
Solubility in water	8.19 g/g (−28.3 °C); 34.97 g/g (−23.9 °C); Miscible (≥ −19.3 °C)
Solubility	Miscible in EtOH, ether, CHCl3
log P	0.33
Vapor pressure	0.32 kPa (20 °C); 0.47 kPa (25 °C); 9.62 kPa (100 °C)
Henry's law; constant (kH)	4.45·10−4 L·atm/mol
Acidity (pKa)	4.88
Thermal conductivity	1.44·105 W/m·K
Refractive index (nD)	1.3843
Viscosity	1.175 cP (15 °C); 1.02 cP (25 °C); 0.668 cP (60 °C); 0.495 cP (90 °C)
Structure
Crystal structure	Monoclinic (−95 °C)
Space group	P21/c
Lattice constant	a = 4.04 Å, b = 9.06 Å, c = 11 Å α = 90°, β = 91.25°, γ = 90°
Dipole moment	0.63 D (22 °C)
Thermochemistry
Specific; heat capacity (C)	152.8 J/mol·K
Std molar; entropy (So298)	191 J/mol·K
Std enthalpy of; formation (ΔfHo298)	−510.8 kJ/mol
Std enthalpy of; combustion (ΔcHo298)	1527.3 kJ/mol
Hazards
Main hazards	Corrosive
Safety data sheet	See: data page
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P280, P305+351+338, P310
EU classification	C
R-phrases	R10, R34
S-phrases	(S1/2), S23, S36, S45
NFPA 704	2 3 0
Flash point	54 °C (129 °F; 327 K)
Autoignition; temperature	512 °C (954 °F; 785 K)
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	1370 mg/kg (white mice, oral)
	US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (30 mg/m3) ST 15 ppm (45 mg/m3)
IDLH (Immediate danger	N.D.
Related compounds
Other anions	Propanoate
Related Carboxylic acids	Acetic acid; Lactic acid; 3-hydroxypropionic acid; Tartronic acid; Acrylic acid; Butyric acid
Related compounds	1-Propanol; Propionaldehyde; Sodium propionate; Propionic anhydride
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references