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Wikipedia

β-Pinene

January 01, 1970

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

β-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
  • 127-91-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:50025 Y
ChEMBL
  • ChEMBL501351 Y
ChemSpider
  • 14198 Y
DrugBank
  • DB15574
ECHA InfoCard 100.004.430
EC Number
  • 204-872-5
KEGG
  • C09882 Y
  • 14896
UNII
  • 4MS8VHZ1HJ Y
  • DTXSID7027049
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 Y
    Key: WTARULDDTDQWMU-UHFFFAOYSA-N Y
  • 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
−6214.1±2.9 kJ/mol[1]
Hazards
GHS labelling:
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)
Health 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).
Y verify (what is YN ?)

β-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-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-Pinene or β-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-Pinene". National Institute of Standards and Technology. Retrieved January 29, 2018.
  2. ^ "(−)-β-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-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. 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.

January 01, 1970
pinene, monoterpene, organic, compound, found, plants, isomers, pinene, other, being, pinene, colorless, liquid, soluble, alcohol, water, woody, green, pine, like, smell, names, iupac, names, dimethyl, methylidenebicyclo, heptanepin, other, names, dimethyl, me. b Pinene is a monoterpene an organic compound found in plants It is one of the two isomers of pinene the other being a pinene It is a colorless liquid soluble in alcohol but not water It has a woody green pine like smell b Pinene Names IUPAC names 6 6 Dimethyl 2 methylidenebicyclo 3 1 1 heptanePin 2 10 ene Other names 6 6 Dimethyl 2 methylenebicyclo 3 1 1 heptane2 10 PineneNopinenePseudopinene Identifiers CAS Number 127 91 3 Y 3D model JSmol Interactive image ChEBI CHEBI 50025 Y ChEMBL ChEMBL501351 Y ChemSpider 14198 Y DrugBank DB15574 ECHA InfoCard 100 004 430 EC Number 204 872 5 KEGG C09882 Y PubChem CID 14896 UNII 4MS8VHZ1HJ Y CompTox Dashboard EPA DTXSID7027049 InChI InChI 1S C10H16 c1 7 4 5 8 6 9 7 10 8 2 3 h8 9H 1 4 6H2 2 3H3 YKey WTARULDDTDQWMU UHFFFAOYSA N YInChI 1 C10H16 c1 7 4 5 8 6 9 7 10 8 2 3 h8 9H 1 4 6H2 2 3H3Key WTARULDDTDQWMU UHFFFAOYAW SMILES C1 C C2CC CC1 C2 C C Properties Chemical formula C 10H 16 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 ofcombustion DcH 298 6214 1 2 9 kJ mol 1 Hazards GHS labelling Pictograms Signal word Danger Hazard statements H226 H304 H315 H317 H410 Precautionary statements 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 130 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 Y verify what is Y N Infobox references b 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 editMany plants from many botanical families contain the compound including Cuminum cyminum 5 6 Humulus lupulus 7 Pinus pinaster 4 Clausena anisata Cannabis sativa 8 Piper nigrum 9 Myristica fragans 9 Citrus aurantiifolia 9 Pistacia lentiscus 9 The clear compund is produced by distillation of turpentine oils 10 Uses editThis section needs expansion You can help by adding to it October 2023 b 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 a Pinene or b 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 a b b Pinene National Institute of Standards and Technology Retrieved January 29 2018 b Pinene Sigma Aldrich Retrieved January 29 2018 Geron C et al 2000 A review and synthesis of monoterpene speciation from forests in the United States Atmospheric Environment 34 11 1761 81 a b Neuenschwander U Meier E Hermans I 2011 Peculiarities of b pinene autoxidation ChemSusChem 4 11 1613 21 doi 10 1002 cssc 201100266 PMID 21901836 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 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 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 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 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 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 amp Co KGaA ISBN 978 3 527 33160 4 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 Mattiello Joseph J 1945 Protective and Decorative Coatings U S Government Printing Office 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 Retrieved from https en wikipedia org w index php title B Pinene amp oldid 1223101852, wikipedia, wiki, book, books, library,

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