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Wikipedia

β-Pinene

February 16, 2024

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 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 ?)

This 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:

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.

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.

February 16, 2024
pinene, monoterpene, organic, compound, found, plants, isomers, pinene, other, being, pinene, colorless, liquid, soluble, alcohol, water, woody, green, pine, like, smell, namesiupac, names, dimethyl, methylidenebicyclo, heptanepin, eneother, names, dimethyl, m. 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 colorless liquid soluble in alcohol but not water It has a woody green pine like smell b Pinene NamesIUPAC names 6 6 Dimethyl 2 methylidenebicyclo 3 1 1 heptanePin 2 10 eneOther names 6 6 Dimethyl 2 methylenebicyclo 3 1 1 heptane2 10 PineneNopinenePseudopineneIdentifiersCAS Number 127 91 3 Y3D model JSmol Interactive imageChEBI CHEBI 50025 YChEMBL ChEMBL501351 YChemSpider 14198 YDrugBank DB15574ECHA InfoCard 100 004 430EC Number 204 872 5KEGG C09882 YPubChem CID 14896UNII 4MS8VHZ1HJ YCompTox Dashboard EPA DTXSID7027049InChI 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 UHFFFAOYAWSMILES C1 C C2CC CC1 C2 C CPropertiesChemical formula C 10H 16Molar mass 136 238 g mol 1Appearance Colorless liquidDensity 0 872 g mLMelting point 61 54 C 78 77 F 211 61 K 1 Boiling point 165 167 C 329 332 F 438 440 K 2 ThermochemistryStd enthalpy ofcombustion DcH 298 6214 1 2 9 kJ mol 1 HazardsGHS labelling PictogramsSignal word DangerHazard statements H226 H304 H315 H317 H410Precautionary 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 P501NFPA 704 fire diamond 130Flash 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 This 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 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 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 Retrieved from https en wikipedia org w index php title B Pinene amp oldid 1190340323, wikipedia, wiki, book, books, library,

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