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{{distinguish|Pine nut oil}} {{distinguish|Pine nut oil}}
{{for|the byproduct of wood pulp production sometimes called pine oil|tall oil}} {{for|the byproduct of wood pulp production sometimes called pine oil|tall oil}}

{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428739560 | verifiedrevid = 476993877
|Reference=<ref name="Merck">''Merck Index'', 11th Edition, '''7416'''.</ref>
| Reference =<ref name="Merck" />
| ImageFile = | ImageFile = PineEssentialOil.png
| ImageSize =
| IUPACName = | ImageSize = 150px
| ImageCaption = Pine (''Pinus sylvestris'') essential oil in a clear glass vial
| OtherNames = Essential oil of pine<br>Yarmor | OtherNames = Essential oil of pine<br />Yarmor
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}} | 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 =
| SMILES =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = NA | 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>
'''Pine oil''' is an ] obtained by the ] of needles, twigs and cones from a variety of species of ], particularly '']''.


==Composition==
It is used in ], as a scent in ] oils, as a cleaning product, and as a ] in small and expensive ] instruments. It is naturally deodorizing, and antibacterial. It may also be used varyingly as a ], ] oil and an ]. It is also used as an effective organic herbicide where its action is to modify the waxy cuticle of plants resulting in desiccation.
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> Other components include ] and ].<ref>{{cite journal |doi=10.1016/j.energy.2013.05.061 |title=Combustion performance and emission characteristics study of pine oil in a diesel engine |date=2013 |last1=Vallinayagam |first1=R. |last2=Vedharaj |first2=S. |last3=Yang |first3=W.M. |last4=Lee |first4=P.S. |last5=Chua |first5=K.J.E. |last6=Chou |first6=S.K. |journal=Energy |volume=57 |pages=344–351 }}</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==
Pine oil is distinguished from other products from pine such as ], the low-boiling fraction from the ] of pine sap, and ], the thick tar remaining after turpentine is distilled.
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.
Chemically, pine oil consists mainly of cyclic ] ]s.<ref name="Merck"/> It may also contain terpene ]s, ]s, and ]s. The exact composition depends on various factors such as the variety of pine it is produced from and the parts of the tree used.


In ] it is used in ] and as a scent in ] oils.
Industrially, pine oil is used in metal extraction from ores.<ref name="Merck"/> For example, in ] pine oil is used to soak all ] ores for froth flotation.


==Properties as a disinfectant== ===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 is a ] disinfectant that is mildly antiseptic.<ref name="PDR"></ref> Pine oil disinfectants are relatively inexpensive and widely available. They are effective against ''Brevibacterium ammoniagenes'', the fungus '']'', '']'', '']'', ] ], 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, '']'', '']'', '']'', '']'', '']'', '']'', '']'', '']'', ''], '']''.<ref>http://www.epa.gov/pesticides/reregistration/REDs/pineoil_red.pdf</ref>
With respect to the quality of indoor air, attention is directed to the effects of ambient ozone on pine oil components.<ref>{{cite journal |doi=10.1111/j.1600-0668.2005.00414.x |title=Cleaning products and air fresheners: Emissions and resulting concentrations of glycol ethers and terpenoids |date=2006 |last1=Singer |first1=B. C. |last2=Destaillats |first2=H. |last3=Hodgson |first3=A. T. |last4=Nazaroff |first4=W. W. |journal=Indoor Air |volume=16 |issue=3 |pages=179–191 |pmid=16683937 |url=https://digital.library.unt.edu/ark:/67531/metadc873484/ }}</ref> Large doses may cause ] depression.<ref name="Merck" />


== See also ==
It will kill the causative agents of ], ] (some agents), ], enteric fever, ], several forms of ], ], ] and several types of dysentery.<ref name="UA"> University of Arizona Veterinary Diagnostic Laboratory, accessed June 26, 2007.</ref> It is also effective against several of the leading causes of food poisoning.{{citation needed|date=June 2007}} It is not effective against spore related illneses such as ] or ] or against non-enveloped viruses such as ], ], ] or ].<ref name="UA"/>
* ]
* ]
* ], 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 ==
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"/> Large doses may cause ] depression.<ref name="Merck"/>
{{reflist|30em}}


== Further reading ==
==References==
* {{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}}
<references/>
* {{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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Latest revision as of 22:36, 8 January 2025

Not to be confused with Pine nut oil. For the byproduct of wood pulp production sometimes called pine oil, see tall oil.
Pine oil

Pine (Pinus sylvestris) essential oil in a clear glass vial
Names
Other names Essential oil of pine
Yarmor
Identifiers
CAS Number
Beilstein Reference 8191505
ChemSpider
  • none
ECHA InfoCard 100.219.894 Edit this at Wikidata
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula Mixture
Appearance Colorless to pale yellow liquid
Density 0.875 g/cm at 25 °C (approximate)
Melting point 5 °C (41 °F; 278 K)
Boiling point 195 °C (383 °F; 468 K)
Solubility in water Insoluble
log P 1.7
Vapor pressure 4 mmHg
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 2 0
Flash point 65 °C (149 °F; 338 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Pine oil is an essential oil obtained from a variety of species of pine, particularly Pinus sylvestris. Typically, parts of the trees that are not used for lumber — stumps, etc. — are ground and subjected to steam distillation. As of 1995, synthetic pine oil was the "biggest single turpentine derivative." Synthetic pine oils accounted for 90% of sales as of 2000.

Composition

Pine oil is a higher boiling fraction from turpentine. Both synthetic and natural pine oil consists mainly of α-terpineol, a C10 alcohol (b.p. 214–217 °C). Other components include dipentene and pinene. The detailed composition of natural pine oil depends on many factors, such as the species of the host plant. Synthetic pine oil is obtained by treating pinene with water in the presence of a catalytic amount of sulfuric acid. This treatment results in hydration of the alkene and rearrangement of the pinene skeleton, yielding terpineols.

Uses

Industrially, pine oil was once used in froth flotation for the separation of mineral from ores. For example, in copper extraction, pine oil is used to condition copper sulfide ores for froth flotation.

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

In alternative medicine it is used in aromatherapy and as a scent in bath oils.

Properties as a disinfectant

Pine oil is used as a cleaning product, disinfectant, sanitizer, microbicide (or microbistat), virucide or insecticide. It is an effective herbicide where its action is to modify the waxy cuticle of plants, resulting in desiccation. Pine oil is a disinfectant that is mildly antiseptic. It is effective against Brevibacterium ammoniagenes, the fungi Candida albicans, Enterobacter aerogenes, Escherichia coli, Gram-negative enteric bacteria, household germs, Gram-negative household germs such as those causing salmonellosis, herpes simplex types 1 and 2, influenza type A, influenza virus type A/Brazil, influenza virus type A2/Japan, intestinal bacteria, Klebsiella pneumoniae, odor-causing bacteria, mold, mildew, Pseudomonas aeruginosa, Salmonella choleraesuis, Salmonella typhi, Salmonella typhosa, Serratia marcescens, Shigella sonnei, Staphylococcus aureus, Streptococcus faecalis, Streptococcus pyogenes, and Trichophyton mentagrophytes.

Safety

With respect to the quality of indoor air, attention is directed to the effects of ambient ozone on pine oil components. Large doses may cause central nervous system depression.

See also

References

  1. ^ Merck Index, 11th Edition, 7416. p. 1182
  2. Boyle, Hal (September 12, 1954). "There's Gold in those Pine Stumps". Sarasota Journal. p. 11.
  3. Chapter 1. Production trade and markets. Rome: Food and Agriculture Organization. 1995. ISBN 978-9251036846. {{cite book}}: |work= ignored (help)
  4. ^ Gscheidmeier, Manfred; Fleig, Helmut (June 15, 2000). "Turpentines, 16. Pine Oil". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_267. ISBN 978-3527306732.
  5. ^ "Reregistration Decision – Pine oil (case 3113)" (PDF). Environmental Protection Agency. October 2006.
  6. Vallinayagam, R.; Vedharaj, S.; Yang, W.M.; Lee, P.S.; Chua, K.J.E.; Chou, S.K. (2013). "Combustion performance and emission characteristics study of pine oil in a diesel engine". Energy. 57: 344–351. doi:10.1016/j.energy.2013.05.061.
  7. Macchioni, F.; Cioni, P. L.; Flamini, G.; Morelli, I.; Maccioni, S.; Ansaldi, M. (2003-03-01). "Chemical Composition of Essential Oils from Needles, Branches and Cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from Central ltaly". Flavour and Fragrance Journal. 18 (2): 139–143. doi:10.1002/ffj.1178. ISSN 1099-1026.
  8. Coleby-Williams, Jerry (April 9, 2004). "Fact Sheet: Organic Weed Control". Gardening Australia. Retrieved August 28, 2016.
  9. "Pine Oil". PDRhealth. 2003. Archived from the original on 2007-09-21.
  10. Singer, B. C.; Destaillats, H.; Hodgson, A. T.; Nazaroff, W. W. (2006). "Cleaning products and air fresheners: Emissions and resulting concentrations of glycol ethers and terpenoids". Indoor Air. 16 (3): 179–191. doi:10.1111/j.1600-0668.2005.00414.x. PMID 16683937.

Further reading

Categories: