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Revision as of 12:24, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473943578 of page Pine_oil for the Chem/Drugbox validation project (updated: '').  Latest revision as of 21:56, 22 August 2024 edit Hohum (talk | contribs)Extended confirmed users, Pending changes reviewers68,461 edits See also 
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{{distinguish|Pine nut oil}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{for|the byproduct of wood pulp production sometimes called pine oil|tall oil}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 464206876
| Watchedfields = changed
|Reference=<ref name="Merck">''Merck Index'', 11th Edition, '''7416'''.</ref>
| verifiedrevid = 476993877
| ImageFile =
| Reference =<ref name="Merck" />
| ImageSize =
| ImageFile = PineEssentialOil.png
| IUPACName =
| ImageSize = 150px
| OtherNames = Essential oil of pine<br>Yarmor
| ImageCaption = Pine (''Pinus sylvestris'') essential oil in a clear glass vial
| Section1 = {{Chembox Identifiers
| OtherNames = Essential oil of pine<br />Yarmor
| CASNo_Ref = {{cascite|correct|CAS}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 8002-09-3 | CASNo = 8002-09-3
| UNII_Ref = {{fdacite|changed|FDA}}
| Beilstein = 8191505
| PubChem = | UNII = HA5CX6676U
| SMILES = | Beilstein = 8191505
| PubChem =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = NA | SMILES =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = none
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = Mixture | Formula = Mixture
| Appearance = Colorless to pale yellow liquid
| MolarMass =
| Density = 0.875 g/cm<sup>3</sup> at 25 °C (approximate)
| Appearance = Colorless to pale yellow liquid
| MeltingPtC = 5
| Density = 0.9 g/cm<sup>3</sup> (approximate)
| MeltingPt = | BoilingPtC = 195
| LogP = 1.7
| BoilingPt = 200-220 °C
| Solubility = Insoluble | Solubility = Insoluble
| VaporPressure =4 mmHg
}}
<!-- Vapor Density: 5.3 -->
| Section3 = {{Chembox Hazards
<!-- Refractive Index: n20/D 1.515 -->
| MainHazards =
| FlashPt =
| Autoignition =
}} }}
|Section3={{Chembox Hazards
| MainHazards =
| NFPA-H = 2
| NFPA-F = 2
| NFPA-R = 0
| NFPA-S =
| FlashPtC = 65
| AutoignitionPtC =
}}
}} }}

'''Pine oil''' is an ] obtained from a variety of species of ], particularly '']''. Typically, parts of the trees that are not used for lumber {{emdash}} stumps, etc. {{emdash}} are ground and subjected to ].<ref name=Boyle>{{cite news |url= https://news.google.com/newspapers?nid=1798&dat=19540913&id=bwQdAAAAIBAJ&pg=6598,929929&hl=en |title= There's Gold in those Pine Stumps |newspaper= Sarasota Journal |first= Hal |last= Boyle |authorlink= Hal Boyle |page= 11 |date= September 12, 1954 }}</ref> As of 1995, synthetic pine oil was the "biggest single ] derivative."<ref>{{cite book |url= http://www.fao.org/docrep/v6460e/v6460e05.htm#turpentine |title= Chapter 1. Production trade and markets |work= Non-Wood Forest Products 2, Gum naval stores: Turpentine and rosin from pine resin |isbn= 978-9251036846 |publisher= ] |location= Rome |year= 1995 }}</ref> Synthetic pine oils accounted for 90% of sales as of 2000.<ref name=Ull>{{Ullmann|title= Turpentines, 16. Pine Oil |first1= Manfred |last1= Gscheidmeier |first2= Helmut |last2= Fleig |date= June 15, 2000 |doi=10.1002/14356007.a27_267|isbn = 978-3527306732}}</ref>

==Composition==
Pine oil is a higher boiling fraction from ]. Both synthetic and natural pine oil consists mainly of ], a C10 alcohol (b.p. 214–217 °C).<ref name=EPA_RED /><ref name="Merck">''Merck Index'', 11th Edition, '''7416'''. p. 1182</ref> The detailed composition of natural pine oil depends on many factors, such as the species of the host plant.<ref>{{Cite journal|last1=Macchioni|first1=F.|last2=Cioni|first2=P. L.|last3=Flamini|first3=G.|last4=Morelli|first4=I.|last5=Maccioni|first5=S.|last6=Ansaldi|first6=M.|date=2003-03-01|title=Chemical Composition of Essential Oils from Needles, Branches and Cones of ''Pinus pinea'', ''P. halepensis'', ''P. pinaster'' and ''P. nigra'' from Central ltaly|journal=Flavour and Fragrance Journal|language=en|volume=18|issue=2|pages=139–143|doi=10.1002/ffj.1178|issn=1099-1026}}</ref> Synthetic pine oil is obtained by treating ] with water in the presence of a catalytic amount of ]. This treatment results in ] of the alkene and rearrangement of the pinene skeleton, yielding terpineols.<ref name=Ull/>

==Uses==
Industrially, pine oil was once used in ] for the separation of mineral from ores.<ref name="Merck" /> For example, in ], pine oil is used to condition ] ores for ].

It is also used as a ] in small and expensive ] instruments.

In ] it is used in ] and as a scent in ] oils.

===Properties as a disinfectant ===
Pine oil is used as a cleaning product, ], ], ] (or ]), ] or ].<ref name=EPA_RED /> It is an effective herbicide where its action is to modify the waxy cuticle of plants, resulting in desiccation.<ref>{{cite web |url= http://www.abc.net.au/gardening/stories/s963151.htm |title= Fact Sheet: Organic Weed Control |publisher= ] |authorlink= Jerry Coleby-Williams |first= Jerry |last= Coleby-Williams |date= April 9, 2004 |accessdate= August 28, 2016 }}</ref> Pine oil is a disinfectant that is mildly antiseptic.<ref name="PDR">{{cite web |url= http://www.pdrhealth.com/drug_info/nmdrugprofiles/herbaldrugs/102230.shtml |archiveurl= https://web.archive.org/web/20070921171154/http://www.pdrhealth.com/drug_info/nmdrugprofiles/herbaldrugs/102230.shtml |title= Pine Oil |website= PDRhealth |date= 2003 |archivedate= 2007-09-21}}</ref> It is effective against ''Brevibacterium ammoniagenes'', the fungi '']'', '']'', '']'', ] ], household germs, Gram-negative household germs such as those causing ], ] types 1 and 2, ], influenza virus type A/Brazil, influenza virus type A2/Japan, intestinal bacteria, '']'', odor-causing bacteria, mold, mildew, '']'', '']'', '']'', '']'', '']'', '']'', '']'', '']'', '']'', and '']''.<ref name=EPA_RED>{{cite web |url= https://archive.epa.gov/pesticides/reregistration/web/pdf/pineoil_red.pdf |title= Reregistration Decision – Pine oil (case 3113) |publisher= Environmental Protection Agency |date= October 2006 }}</ref>

== Safety ==
Pine oil has a relatively low human toxicity level, a low corrosion level and limited persistence; however, it irritates the skin and mucous membranes and has been known to cause breathing problems.<ref name="PDR" /><ref>{{cite web |url= https://medlineplus.gov/ency/article/002733.htm |title= Pine Oil Poisoning |website= Medlineplus.gov |accessdate= August 28, 2016 }}</ref> Large doses may cause ] depression.<ref name="Merck" />

== See also ==
* ]
* ]
* ], cleaning product that originally contained pine oil, though it switched to a different active ingredient in 2013 due to the declining availability of pine oil

== References ==
{{reflist|30em}}

== Further reading ==
* {{cite book |title= Turpentines, 16. Pine Oil |work= ] |first1= Manfred |last1= Gscheidmeier |first2= Helmut |last2= Fleig |date= June 15, 2000 |doi=10.1002/14356007.a27_267|chapter = Turpentines|isbn = 978-3527306732}}
* {{cite book |chapter-url= http://www.fao.org/docrep/v5350e/V5350e10.htm |title= TURPENTINE FROM PINE RESIN |chapter= 8 |work= Non-Wood Forest Products 1, Flavours and fragrances of plant origin |isbn= 978-92-5-103648-8 |publisher= ] |location= Rome |year= 1995 |archive-url=https://web.archive.org/web/20110117124839/http://www.fao.org/docrep/v5350e/V5350e10.htm |archive-date=January 17, 2011}}

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