Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 12:04, 3 August 2011 editCoolKoon (talk | contribs)Extended confirmed users, Pending changes reviewers2,163 editsm →Uses← Previous edit		Latest revision as of 18:02, 11 September 2024 edit undoCitation bot (talk | contribs)Bots5,424,096 edits Altered issue. Add: pmid, bibcode, authors 1-1. Removed parameters. Formatted dashes. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Abductive | Category:E-number additives | #UCB_Category 310/313
(100 intermediate revisions by 75 users not shown)
Line 1:		Line 1:
	{{POV-check|date=December 2007}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 396931528
			| Watchedfields = changed
⚫	|Reference=<ref>''Merck Index'', 11th Edition, '''1705'''.</ref>
		⚫	| verifiedrevid = 442834022
	|ImageFile=Calcium propanoate.png
		⚫	| Reference = <ref>''Merck Index'', 11th Edition, '''1705'''.</ref>
	|ImageSize=200px
	|IUPACName=Calcium propanoate		| ImageFile = Calcium propanoate.png
	|OtherNames=Calcium propionate<br>Mycoban		| PIN = Calcium dipropanoate
			| OtherNames = Calcium propionate<br>Calcium dipropionate<br>Mycoban
	|Section1= {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| CASNo=4075-81-4
			| CASNo_Ref = {{cascite|correct|??}}
⚫	| PubChem=19999
	| EINECS =223-795-8		| CASNo=4075-81-4
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES=CCC(=O).CCC(=O).
			| UNII = 8AI80040KW
		⚫	| PubChem=19999
			| EINECS =223-795-8
			| KEGG = D09875
		⚫	| SMILES=CCC(=O).CCC(=O).
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 18840
			| InChI = 1/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2
			| InChIKey = BCZXFFBUYPCTSJ-NUQVWONBAE
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = BCZXFFBUYPCTSJ-UHFFFAOYSA-L
	}}		}}
	|Section2= {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula=C<sub>6</sub>H<sub>10</sub>CaO<sub>4</sub>		| Formula=C<sub>6</sub>H<sub>10</sub>CaO<sub>4</sub>
	| MolarMass=186.22		| MolarMass=186.2192 g/mol
	| Appearance=White crystalline solid		| Appearance =White crystalline solid
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=300 °C
	| BoilingPt=		| BoilingPt=
	| Solubility=Freely soluble		| Solubility= 49 g/100 mL (0 °C) <br> 55.8 g/100 mL (100 °C)
			| SolubleOther = slightly soluble in ], ] <br> insoluble in ], ]
	}}		}}
	|Section3= {{Chembox Hazards		| Section3 = {{Chembox Structure
			| CrystalStruct = monoclinic
⚫	| MainHazards=
			}}
⚫	| FlashPt=
			| Section4 = {{Chembox Hazards
	| Autoignition=
		⚫	| MainHazards=
		⚫	| FlashPt=
			| AutoignitionPt =
			| NFPA-H = 2
			| NFPA-F = 1
			| NFPA-R = 0
	}}		}}
	}}		}}
Line 32:		Line 51:
	==Uses==		==Uses==
	As a food additive, it is listed as ] 282 in the ]. Calcium propanoate is used as a preservative in a wide variety of products, including but not limited to bread, other baked goods, processed meat, whey, and other dairy products.<ref name="alimentarius"></ref> In agriculture, it is used, amongst other things, to prevent ] in cows and as a feed supplement <ref name="feed"></ref> Propanoates prevent microbes from producing the energy they need, like benzoates do. However, unlike benzoates, propanoates do not require an acidic environment.<ref name="ingredients">{{cite web | title=Ingredients -- Calcium propionate| url=http://sci-toys.com/ingredients/calcium_propionate.html| accessdate=2007-03-10}}</ref>		As a food additive, it is listed as ] 282 in the ]. Calcium propionate is used as a preservative in a wide variety of products, including: bread, other baked goods, processed meat, whey, and other dairy products.<ref name="alimentarius"> {{webarchive|url=https://web.archive.org/web/20061021214228/http://www.codexalimentarius.net/gsfaonline/additives/details.html?id=306 |date=2006-10-21 }}</ref> In agriculture, it is used, amongst other things, to prevent ] in cows and as a feed supplement.<ref name="feed"></ref> Propionates prevent microbes from producing the energy they need, like benzoates do. However, unlike benzoates, propionates do not require an acidic environment.<ref name="ingredients">{{cite web | title=Ingredients -- Calcium propionate| url=http://sci-toys.com/ingredients/calcium_propionate.html| access-date=2007-03-10}}</ref>
	Calcium propanoate is used in bakery products as a mold inhibitor, typically at 0.1-0.4% <ref>http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html</ref> (though animal feed may contain up to 1%). Mold contamination is considered a serious problem amongst bakers, and conditions commonly found in baking present near-optimal conditions for mold growth.<ref name="baking industry">{{cite web | title=Keeping molds, bacteria at bay| url=http://bakingmanagement.bakery-net.com/article/7448| accessdate=2007-03-24}}</ref>		Calcium propionate is used in bakery products as a mold inhibitor, typically at 0.1–0.4%<ref>{{cite web |url=http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html |title=NYSAES&#124;FST&#124;FVC&#124;Venture 3&#124; Chemical Food Preservatives |access-date=2010-02-28 |url-status=dead |archive-url=https://web.archive.org/web/20100412155551/http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html |archive-date=2010-04-12 }}</ref> (though animal feed may contain up to 1%). Mold contamination is considered a serious problem amongst bakers, and conditions commonly found in baking present near-optimal conditions for mold growth.<ref name="baking industry">{{cite web |title=Keeping molds, bacteria at bay |url=http://bakingmanagement.bakery-net.com/article/7448 |archive-url=https://web.archive.org/web/20080320010015/http://bakingmanagement.bakery-net.com/article/7448 |archive-date=2008-03-20 |access-date=2007-03-24}}</ref>
	A few decades ago, '']'' (rope), was a serious problem,{{Fact|date=February 2007}} but today's improved sanitary practices in the bakery, combined with rapid turnover of the finished product, have virtually eliminated this form of spoilage.{{Fact|date=February 2007}} Calcium propanoate and ] are effective against both '']'' rope and mold.{{Fact|date=February 2007}}		A few decades ago, '']'' (rope), was a serious problem,<ref>Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.</ref> but today's improved sanitary practices in the bakery, combined with rapid turnover of the finished product, have virtually eliminated this form of spoilage.<ref>{{Cite journal |last1=Thompson |first1=Jackie M. |last2=Dodd |first2=Christine E.R. |last3=Waites |first3=Will M. |date=1993 |title=Spoilage of bread by bacillus |url=https://linkinghub.elsevier.com/retrieve/pii/0964830593900395 |journal=International Biodeterioration & Biodegradation |language=en |volume=32 |issue=1–3 |pages=55–66 |doi=10.1016/0964-8305(93)90039-5|bibcode=1993IBiBi..32...55T }}</ref> Calcium propionate and ] are effective against both ''B. mesentericus'' rope and mold.<ref>Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.</ref>
		⚫	Metabolism of ] begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propanoic acid has three carbons, propionyl-CoA cannot directly enter the ] or the ]s. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. A vitamin B<sub>12</sub>–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.
	A small study in children (n=27) found statistically significant "rritability, restlessness, inattention and sleep disturbance in some children" on challenge with calcium propionate preserved food, but noted lack of significance of assessment scores due to placebo response from four subjects. <ref name="pubmed">Dengate S, Ruben A., 2002. J Paediatr Child Health 38(4):373-6.{{cite web | title=Controlled trial of cumulative behavioural effects of a common bread preservative.| url=http://www.ncbi.nlm.nih.gov/sites/entrez?db=pubmed&cmd=DetailsSearch&term=12173999| accessdate=2010-02-20}}</ref>
			Children were challenged with calcium propionate or placebo through daily bread in a double-blind placebo-controlled crossover trial. Although there was no significant difference by two measures, a statistically significant difference was found in the proportion of children whose behaviours "worsened" with challenge (52%), compared to the proportion whose behaviour "improved" with challenge (19%).<ref name = dengate-rubin>{{cite journal
⚫	Metabolism of ] begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propanoic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation nor 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.
			|author1=S. Dengate |author2=A. Rubin | journal = Journal of Paediatrics and Child Health
			| title = Controlled trial of cumulative behavioural effects of a common bread preservative
⚫	Intraventricular infusion of propanoic acid into rat brains caused oxidative stress and produced reversible behavior (e.g. hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g. innate neuroinflammation, glutathione depletion) reminiscent of ].<ref name = macfabe>{{cite journal
			| year = 2002
⚫	| author = D. F. MacFabe, D. P. Cain, K. Rodriguez-Capote, A. E. Franklin, J. E. Hoffman, F. Boon, A. R. Taylor, M. Kavaliers and K.-P. Ossenkopp
			| volume = 38
	| journal = Behavioral Brain Research
			| issue = 4
			| pages = 373–376
			| doi = 10.1046/j.1440-1754.2002.00009.x
		⚫	|pmid=12173999 |s2cid=24898218 }}</ref> When propanoic acid was infused directly into rodents' brains, it produced reversible behavior changes (e.g. hyperactivity, dystonia, social impairment, ]) and brain changes (e.g. innate neuroinflammation, glutathione depletion) partially mimicking human ].<ref name = macfabe>{{cite journal
		⚫	|author1=D. F. MacFabe |author2=D. P. Cain |author3=K. Rodriguez-Capote |author4=A. E. Franklin |author5=J. E. Hoffman |author6=F. Boon |author7=A. R. Taylor |author8=M. Kavaliers |author9=K.-P. Ossenkopp | journal = Behavioural Brain Research
	| title = Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders		| title = Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders
	| year = 2007		| year = 2007
Line 51:		Line 75:
	| pages = 149–169		| pages = 149–169
	| doi = 10.1016/j.bbr.2006.07.025		| doi = 10.1016/j.bbr.2006.07.025
	| url = }}</ref>		| pmid=16950524 |s2cid=3054752 }}</ref>
	According to the Pesticide Action Network North America, calcium propionate is slightly toxic.<ref></ref> This rating is not uncommon for food products; ] is also rated by the same standards as being slightly toxic. <ref></ref> Calcium propanoate can be used as a pesticide.<ref>{{cite journal | last1 = Biggs | first1 = A. R. | last2 = El-Kholi | first2 = M. M. | last3 = El-Neshawy | first3 = S. | last4 = Nickerson | first4 = R. | title = Effects of Calcium Salts on Growth, Polygalacturonase Activity, and Infection of Peach Fruit by Monilinia fructicola | journal = Plant Disease | volume = 81 | pages = 399 | year = 1997 | doi = 10.1094/PDIS.1997.81.4.399}}</ref>		Calcium propionate can be used as a fungicide on fruit.<ref>{{cite journal | last1 = Biggs | first1 = A. R. | last2 = El-Kholi | first2 = M. M. | last3 = El-Neshawy | first3 = S. | last4 = Nickerson | first4 = R. | title = Effects of Calcium Salts on Growth, Polygalacturonase Activity, and Infection of Peach Fruit by Monilinia fructicola | journal = Plant Disease | volume = 81 | pages = 399–403 | year = 1997 | doi = 10.1094/PDIS.1997.81.4.399 | issue = 4| pmid = 30861823 | doi-access = }}</ref>
			In a 1973 study reported by the ], the waterborne administration of 180&nbsp;] of calcium propionate was found to be slightly toxic to ].<ref>{{cite web|url=http://www.ipmcenters.org/Ecotox/Details.cfm?RecordID=18447|title=OPP PESTICIDE ECOTOXICITY DATABASE - Details - Pesticide: Calcium propionate|publisher=EPA / USDA / NIFA|access-date=2019-01-22|archive-url=https://web.archive.org/web/20190123010651/http://www.ipmcenters.org/Ecotox/Details.cfm?RecordID=18447|archive-date=2019-01-23|url-status=dead}}</ref>
			In a recent well-designed translational study, human subjects fed 500&nbsp;mg of calcium propionate twice daily demonstrated a modest decrease in LDL and total cholesterol, without a change in HDL. The study, only eight weeks in length, requires additional studies of both verification and longer duration to demonstrate the clinical value of this chemical. The study identified a novel regulatory circuit that links the gut microbiota metabolite propionic acid (PA), a short-chain fatty acid, with the gut immune system to control intestinal cholesterol homeostasis .<ref>{{cite journal |last1=Haghikia |first1=Arash |last2=Zimmermann |first2=Friederike |last3=Schumann |first3=Paul |title=Propionate attenuates atherosclerosis by immune-dependent regulation of intestinal cholesterol metabolism |journal=European Heart Journal |date=7 Feb 2022 |volume=43 |issue=6 |pages=518–533 |doi=10.1093/eurheartj/ehab644 |pmid=34597388 |pmc=9097250 }}</ref>
	==References==		==References==
			{{Reflist}}
	<references/>
			<references group="13. Haghikia A, Zimmermann F, Schumann P, Jasina A, Roessler J, Schmidt D, Heinze P, Kaisler J, Nageswaran V, Aigner A, Ceglarek U, Cineus R, Hegazy AN, van der Vorst EPC, Döring Y, Strauch CM, Nemet I, Tremaroli V, Dwibedi C, Kränkel N, Leistner DM, Heimesaat MM, Bereswill S, Rauch G, Seeland U, Soehnlein O, Müller DN, Gold R, Bäckhed F, Hazen SL, Haghikia A, Landmesser U. Propionate attenuates atherosclerosis by immune-dependent regulation of intestinal cholesterol metabolism. Eur Heart J. 2021 Oct 1:ehab644. doi: 10.1093/eurheartj/ehab644. Epub ahead of print. PMID 34597388. doi.org/10.1093/eurheartj/ehab644" />
	==External links==		==External links==
		⚫	*
	*
⚫	*
			{{Calcium compounds}}
	]		]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]
	]