Chemistry:Β-Pinene

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β-Pinene
Beta-pinen.svg
(1S)-(-)-beta-pinene-2D-projected-skeletal.png
(1S)-(−)-beta-pinene-from-xtal-3D-balls.png
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
EC Number
  • 204-872-5
KEGG
UNII
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 pictograms GHS02: FlammableGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
H226, H304, H315, H317, H410
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+310, P302+352, P303+361+353, P321, P331, P332+313, P333+313, P362, P363, P370+378, P391, P403+235, P405, P501
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
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).
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Infobox references
Tracking categories (test):

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.

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

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

Uses

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

  1. 1.0 1.1 "β-Pinene". National Institute of Standards and Technology. 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. 
  2. "(−)-β-Pinene". Sigma-Aldrich. https://www.sigmaaldrich.com/catalog/product/aldrich/402753?lang=pt&region=BR. 
  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. 4.0 4.1 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. 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.