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{{DISPLAYTITLE:''beta''-Pinene}}
{{DISPLAYTITLE:βべーた-Pinene}}
{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
Line 8: Line 8:
| ImageFileL1 = (1S)-(-)-beta-pinene-2D-projected-skeletal.png
| ImageFileL1 = (1S)-(-)-beta-pinene-2D-projected-skeletal.png
| ImageFileR1 = (1S)-(−)-beta-pinene-from-xtal-3D-balls.png
| ImageFileR1 = (1S)-(−)-beta-pinene-from-xtal-3D-balls.png
| PIN = 6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptane
| IUPACName = 6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptane<br />Pin-2(10)-ene
| OtherNames = 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane<br />2(10)-Pinene<br />Nopinene<br />Pseudopinene
| OtherNames = 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane<br />2(10)-Pinene<br />Nopinene<br />Pseudopinene
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| CASNo = 127-91-3
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| ChEMBL = 501351
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| ChEBI = 50025
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID=14198
| DrugBank = DB15574
| EINECS = 204-872-5
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09882
| KEGG = C09882
⚫
| PubChem = 14896
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 4MS8VHZ1HJ
| InChI = 1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
| InChI = 1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
| InChIKey = WTARULDDTDQWMU-UHFFFAOYAW
| InChIKey = WTARULDDTDQWMU-UHFFFAOYAW
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| ChEMBL = 501351
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
| StdInChI = 1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WTARULDDTDQWMU-UHFFFAOYSA-N
| StdInChIKey = WTARULDDTDQWMU-UHFFFAOYSA-N
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| CASNo = 127-91-3
⚫
| PubChem = 14896
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 4MS8VHZ1HJ
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| ChEBI = 50025
| SMILES = C1(=C)C2CC(CC1)C2(C)C
| SMILES = C1(=C)C2CC(CC1)C2(C)C
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID=14198
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
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| Appearance = Colorless liquid
| Appearance = Colorless liquid
| Density = 0.872 g/mL
| Density = 0.872 g/mL
| MeltingPt = 211.61 K
| MeltingPtK = 211.61
| MeltingPt_ref = <ref>{{Cite book | title =http://webbook.nist.gov/cgi/cbook.cgi?Name=beta-pinene&Units=SI&cTG=on&cIR=on&cTC=on&cTZ=on&cTP=on&cMS=on&cTR=on&cUV=on&cIE=on&cGC=on&cIC=on&cES=on&cDI=on&cSO=on visited on 01/29/2018 }}</ref>
| MeltingPt_ref = <ref name="auto">{{cite web | url = http://webbook.nist.gov/cgi/cbook.cgi?Name=beta-pinene&Units=SI&cTG=on&cIR=on&cTC=on&cTZ=on&cTP=on&cMS=on&cTR=on&cUV=on&cIE=on&cGC=on&cIC=on&cES=on&cDI=on&cSO=on | title = βべーた-Pinene | access-date = January 29, 2018 | publisher = [[National Institute of Standards and Technology]] }}</ref>
| BoilingPt = 438-440 K
| BoilingPtK = 438-440
| BoilingPt_ref = <ref>{{ title =https://www.sigmaaldrich.com/catalog/product/aldrich/402753?lang=pt&region=BR visited on 01/29/2018 }}</ref>
| BoilingPt_ref = <ref>{{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/402753?lang=pt&region=BR | title = (−)-βべーた-Pinene | access-date = January 29, 2018 | publisher = [[Sigma-Aldrich]] }}</ref>
| Solubility =
| Solubility =
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Thermochemistry
| DeltaHc = {{val|-6214.1|2.9|u=kJ/mol}}<ref name="auto"/>
}}
|Section4={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPtC = 36
| FlashPtC = 36
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| NFPA-F = 3
| NFPA-F = 3
| NFPA-R = 0
| NFPA-R = 0
| RPhrases = {{R10}} {{R36}} {{R37}} {{R38}}
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S36}}
| HPhrases = {{H-phrases|226|304|315|317|410}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|272|273|280|301+310|302+352|303+361+353|321|331|332+313|333+313|362|363|370+378|391|403+235|405|501}}
}}
}}
}}
}}


'''''beta''-Pinene''' ('''βべーた-pinene''') is a [[monoterpene]], an organic compound found in plants. It is one of the two [[isomer]]s of [[pinene]], the other being [[alpha-Pinene|αあるふぁ-pinene]]. It is [[color]]less [[liquid]] [[solubility|soluble]] in [[alcohol]], but not [[water]]. It has a [[wood]]y-green [[pine]]-like [[odour|smell]].
'''βべーた-Pinene''' is a [[monoterpene]], an organic compound found in plants. It is one of the two [[isomer]]s of [[pinene]], the other being [[alpha-Pinene|αあるふぁ-pinene]]. It is a [[color]]less [[liquid]] [[solubility|soluble]] in [[ethanol|alcohol]], but not [[water]]. It has a [[wood]]y-green [[pine]]-like [[odour|smell]].


This is one of the most abundant compounds released by forest trees.<ref>Geron, C., et al. (2000). [http://hero.epa.gov/index.cfm?action=reference.details&reference_id=19095 A review and synthesis of monoterpene speciation from forests in the United States.] ''Atmospheric Environment'' 34(11), 1761-81.</ref> If oxidized in air, the [[allylic]] products of the [[pinocarveol]] and [[myrtenol]] family prevail.<ref name=herm>Neuenschwander, U., et al. (2011). [https://www.ncbi.nlm.nih.gov/pubmed/21901836 Peculiarities of βべーた-pinene autoxidation.] ''ChemSusChem'' 4(11), 1613-21.</ref>
βべーた-Pinene is one of the most abundant compounds released by forest trees.<ref>Geron, C., et al. (2000). [http://hero.epa.gov/index.cfm?action=reference.details&reference_id=19095 A review and synthesis of monoterpene speciation from forests in the United States.] ''Atmospheric Environment'' 34(11), 1761-81.</ref> If oxidized in air, the [[allylic]] products of the [[pinocarveol]] and [[myrtenol]] family prevail.<ref name=herm>{{cite journal | pmid = 21901836| year = 2011| last1 = Neuenschwander| first1 = U.| last2 = Meier| first2 = E.| last3 = Hermans| first3 = I.| title = Peculiarities of βべーた-pinene autoxidation| journal = ChemSusChem| volume = 4| issue = 11| pages = 1613–21| doi = 10.1002/cssc.201100266}}</ref>


== Sources ==
== Plants that contain βべーた-pinene ==
Many plants from many botanical families contain the compound, including:
Many plants from many botanical families contain the compound, including:


* ''[[Cuminum cyminum]]''<ref name=li>Li, R. and Z. T. Jiang. (2004). [http://onlinelibrary.wiley.com/doi/10.1002/ffj.1302/abstract Chemical composition of the essential oil of ''Cuminum cyminum'' L. from China.] ''Flavour and Fragrance Journal'' 19(4), 311-13.</ref><ref>Wang, L., et al. (2009). [https://www.ncbi.nlm.nih.gov/pubmed/19576388 Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in ''Cuminum cyminum'' L.] ''Analytica Chimica Acta'' 647(1), 72-77.</ref>
* ''[[Cuminum cyminum]]''<ref name=li>{{cite journal | doi = 10.1002/ffj.1302| title = Chemical composition of the essential oil of ''Cuminum'' cyminum L. From China| year = 2004| last1 = Li| first1 = Rong| last2 = Jiang| first2 = Zi-Tao| journal = Flavour and Fragrance Journal| volume = 19| issue = 4| pages = 311–313}}</ref><ref>{{cite journal | pmid = 19576388 | year = 2009 | last1 = Wang | first1 = L. | last2 = Wang | first2 = Z. | last3 = Zhang | first3 = H. | last4 = Li | first4 = X. | last5 = Zhang | first5 = H. | title = Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in Cuminum cyminum L | journal = Analytica Chimica Acta | volume = 647 | issue = 1 | pages = 72–7 | doi = 10.1016/j.aca.2009.05.030 }}</ref>
*''[[Humulus lupulus]]''<ref>Tinseth, G. [http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer.] ''Brewing Techniques'' January/February 1994. Accessed July 21, 2010.</ref>
*''[[Humulus lupulus]]''<ref>Tinseth, G. [http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer.] {{Webarchive|url=https://web.archive.org/web/20131111102913/http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html |date=2013-11-11 }} ''Brewing Techniques'' January/February 1994. Accessed July 21, 2010.</ref>
* ''[[Pinus pinaster]]''<ref name=herm/>
* ''[[Pinus pinaster]]''<ref name=herm/>
* ''[[Clausena anisata]]''
* ''[[Clausena anisata]]''
* ''[[Cannabis sativa]]''<ref>{{Cite journal|last=Hillig|first=Karl W|date=October 2004|title=A chemotaxonomic analysis of terpenoid variation in Cannabis|journal=Biochemical Systematics and Ecology|volume=32|issue=10|pages=875–891|doi=10.1016/j.bse.2004.04.004|issn=0305-1978}}</ref>
* ''[[Cannabis sativa]]''
* ''[[Black pepper|Piper nigrum]]''<ref name=":0">{{Cite book |last=Santana de Oliveira |first=Mozaniel |title=Essential oils: applications and trends in food science and technology |date=2022 |publisher=Springer |isbn=978-3-030-99476-1 |location=Cham, Switzerland}}</ref>
* ''[[Cannabis indica]]''
* ''[[Myristica fragrans|Myristica fragans .]]''<ref name=":0" />
* ''[[Key lime|Citrus aurantiifolia]]''<ref name=":0" />
* ''[[Pistacia lentiscus]]''<ref name=":0" />
The clear compund is produced by [[distillation]] of [[Turpentine|turpentine oils]].<ref name=":1">{{Cite book |last1=Surburg |first1=Horst |title=Common fragrance and flavor materials: preparation, properties and uses |last2=Panten |first2=Johannes |date=2016 |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |isbn=978-3-527-33160-4 |edition=6. completely revised and updated |location=Weinheim}}</ref>


==See also==
==Uses==
{{expand section|date=October 2023}}
* [[Lemon]]
βべーた-Pinene is used in fragrances and essential oils. It is also used in the production of other [[Aroma compound|aroma compounds]], such as [[myrcene]] and [[nerol]] (got by careful fractional distillation of crude nerol got from myrcene<ref>{{Cite book |last=Opdyke |first=D. L. J. |url=https://books.google.com/books?id=IDkvBQAAQBAJ |title=Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology |date=2013-10-22 |publisher=Elsevier |isbn=978-1-4831-4797-0 |language=en}}</ref>). The myrcene is got by pyrolysis of αあるふぁ-Pinene or βべーた-Pinene.<ref>{{Cite book |last=Mattiello |first=Joseph J. |url=https://books.google.com/books?id=2GouxJ7nsuYC |title=Protective and Decorative Coatings |date=1945 |publisher=U.S. Government Printing Office |language=en}}</ref> Reacting with [[formaldehyde]], result is nopol. When nopol is [[Acetylation|acetylated]], the result is nopyl acetate, which is used as fragrance material.<ref name=":1" /><ref>{{Cite book |last=Opdyke |first=D. L. J. |url=https://books.google.com/books?id=IDkvBQAAQBAJ |title=Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology |date=2013-10-22 |publisher=Elsevier |isbn=978-1-4831-4797-0 |language=en}}</ref>


==References==
==References==
Line 77: Line 89:
[[Category:Flavors]]
[[Category:Flavors]]
[[Category:Perfume ingredients]]
[[Category:Perfume ingredients]]
[[Category:Alkenes]]
[[Category:Vinylidene compounds]]
[[Category:Monoterpenes]]
[[Category:Monoterpenes]]
[[Category:Bicyclic compounds]]
[[Category:Bicyclic compounds]]

Latest revision as of 22:13, 9 May 2024

βべーた-Pinene
Names
IUPAC names
6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptane
Pin-2(10)-ene
Other names
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane
2(10)-Pinene
Nopinene
Pseudopinene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.430 Edit this at Wikidata
EC Number
  • 204-872-5
KEGG
UNII
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 checkY
    Key: WTARULDDTDQWMU-UHFFFAOYSA-N checkY
  • InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
    Key: WTARULDDTDQWMU-UHFFFAOYAW
  • C1(=C)C2CC(CC1)C2(C)C
Properties
C10H16
Molar mass 136.238 g·mol−1
Appearance Colorless liquid
Density 0.872 g/mL
Melting point −61.54 °C; −78.77 °F; 211.61 K[1]
Boiling point 165–167 °C; 329–332 °F; 438–440 K[2]
Thermochemistry
Std enthalpy of
combustion (ΔでるたcH⦵298)
 −6214.1±2.9 kJ/mol[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H315, H317, H410
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 36 °C (97 °F; 309 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

βべーた-Pinene is a monoterpene, an organic compound found in plants. It is one of the two isomers of pinene, the other being αあるふぁ-pinene. It is a colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

βべーた-Pinene is one of the most abundant compounds released by forest trees.[3] If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.[4]

Sources[edit]

Many plants from many botanical families contain the compound, including:

The clear compund is produced by distillation of turpentine oils.[10]

Uses[edit]

βべーた-Pinene is used in fragrances and essential oils. It is also used in the production of other aroma compounds, such as myrcene and nerol (got by careful fractional distillation of crude nerol got from myrcene[11]). The myrcene is got by pyrolysis of αあるふぁ-Pinene or βべーた-Pinene.[12] Reacting with formaldehyde, result is nopol. When nopol is acetylated, the result is nopyl acetate, which is used as fragrance material.[10][13]

References[edit]

  1. ^ a b "βべーた-Pinene". National Institute of Standards and Technology. Retrieved January 29, 2018.
  2. ^ "(−)-βべーた-Pinene". Sigma-Aldrich. Retrieved January 29, 2018.
  3. ^ Geron, C., et al. (2000). A review and synthesis of monoterpene speciation from forests in the United States. Atmospheric Environment 34(11), 1761-81.
  4. ^ a b Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of βべーた-pinene autoxidation". ChemSusChem. 4 (11): 1613–21. doi:10.1002/cssc.201100266. PMID 21901836.
  5. ^ Li, Rong; Jiang, Zi-Tao (2004). "Chemical composition of the essential oil of Cuminum cyminum L. From China". Flavour and Fragrance Journal. 19 (4): 311–313. doi:10.1002/ffj.1302.
  6. ^ Wang, L.; Wang, Z.; Zhang, H.; Li, X.; Zhang, H. (2009). "Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in Cuminum cyminum L". Analytica Chimica Acta. 647 (1): 72–7. doi:10.1016/j.aca.2009.05.030. PMID 19576388.
  7. ^ Tinseth, G. The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer. Archived 2013-11-11 at the Wayback Machine Brewing Techniques January/February 1994. Accessed July 21, 2010.
  8. ^ Hillig, Karl W (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology. 32 (10): 875–891. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978.
  9. ^ a b c d Santana de Oliveira, Mozaniel (2022). Essential oils: applications and trends in food science and technology. Cham, Switzerland: Springer. ISBN 978-3-030-99476-1.
  10. ^ a b Surburg, Horst; Panten, Johannes (2016). Common fragrance and flavor materials: preparation, properties and uses (6. completely revised and updated ed.). Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 978-3-527-33160-4.
  11. ^ Opdyke, D. L. J. (2013-10-22). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0.
  12. ^ Mattiello, Joseph J. (1945). Protective and Decorative Coatings. U.S. Government Printing Office.
  13. ^ Opdyke, D. L. J. (2013-10-22). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0.
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