Pinene


Pinene

Chembox new
Name = Pinene
ImageFile = Alpha-pinen.png ImageSize = 150px
ImageName = Pinene
IUPACName = Pinene
OtherNames =
Section1 = Chembox Identifiers
SMILES =
CASOther = [80-56-8] (unspecified)
[7785-70-8] (1"R"-α)
[7785-26-4] (1"S"-α)
[2437-95-8] ((±)-α)
[18172-67-3] (β)
RTECS =

Section2 = Chembox Properties
Formula = C10H16
MolarMass = 136.24 g/mol
Appearance = Liquid
Density = 0,86 g·cm−3 (alpha, 15 °C)GESTIS|CAS=80-56-8|Name=alpha-Pinen|Datum=24. Januar 2008] GESTIS|ZVG=492888|Name=beta-Pinen|Datum=24. Januar 2008]
Solubility = Practically insoluble in water
MeltingPt = −62–−55 °C (alpha)
BoilingPt = 155–156 °C (alpha)
The chemical compound pinene is a bicyclic terpene (C10H16, 136.24 g/mol) known as a monoterpene Ref|Mann. There are two structural isomers found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, and more widely in other plants. Both are also used by many insects in their chemical communication system.

Systematic names are (1"S",5"S")-2,6,6-trimethylbicyclo [3.1.1] hept-2-ene and (1"S",5"S")-6,6-dimethyl-2-methylenebicyclo [3.1.1] heptane.

Isomers



Biosynthesis

α-Pinene and β-pinene are both produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate followed by loss of a proton from the carbocation equivalent.

Usage

Selective oxidation of pinene with some catalysts in chemical industry give many components for pharmacy, artificial odorants and so on. The primary oxidation product is verbenone.

It can form by simple air oxidation but a synthetic method employs lead tetraacetate Ref|orgsyn.

Pinenes form the primary constituents of turpentine.

References


# J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe, J. B. Harborne, "Natural Products", pp309-311, Addison Wesley Longman Ltd., Harlow, UK, 1994. ISBN 0-582-06009-5.
# Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995). [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv9p0745 Article]

External links


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Look at other dictionaries:

  • Pinene — (Betonung auf der zweiten Silbe: Pinen ) sind Monoterpen Kohlenwasserstoffe, farblose Flüssigkeiten mit der Summenformel C10H16. Pinene sind Bestandteile ätherischer Öle. Inhaltsverzeichnis 1 Vertreter 2 Biosynthese 3 Eigenschaften …   Deutsch Wikipedia

  • pinène — ● pinène nom masculin (latin pinus, pin) Hydrocarbure monoterpénique C10H16, extrait de la résine de pin. pinène [pinɛn] n. m. ÉTYM. 1903, Rev. gén. des sc., no 4, p. 222; cf. Acide pinique, 1842; du lat. pinus « pin », et suff. ène. ❖ …   Encyclopédie Universelle

  • Pinene —   [zu lateinisch pinus »Fichte«, »Kiefer«], Singular Pinen das, s, Bezeichnung für drei isomere, ungesättigte bizyklische Terpenkohlenwasserstoffe (α , β und δ Pinene), denen die Ringstruktur des (in der Natur nicht vorkommenden gesättigten)… …   Universal-Lexikon

  • pinene — [pī′nēn΄] n. [ PINE1 + ENE] either of two isomeric terpenes, C10H16, occurring in oil of turpentine and other essential oils: used as a solvent, in synthetic resins, etc …   English World dictionary

  • Pinene — Alpha pinène α pinène Structure de l α pinène Général Nom IUPAC trimethyl …   Wikipédia en Français

  • pinene — /puy neen/, n. Chem. a liquid terpene, C10H16, the principal constituent of oil of turpentine, found in other essential oils: used chiefly in the manufacture of camphor. [1880 85; PINE1 + ENE] * * * ▪ chemical compound       either of two… …   Universalium

  • pinene — ˈpīˌnēn noun ( s) Etymology: International Scientific Vocabulary pin (from Latin pinus pine) + ene more at pine : either of two liquid isomeric unsaturated bicyclic terpene hydrocarbons C10H16 derived …   Useful english dictionary

  • pinene — pinenas statusas T sritis chemija apibrėžtis Terpenas. formulė C₁₀H₁₆ atitikmenys: angl. pinene rus. пинен …   Chemijos terminų aiškinamasis žodynas

  • pinene — noun Etymology: International Scientific Vocabulary, from Latin pinus Date: 1885 either of two liquid isomeric unsaturated bicyclic terpene hydrocarbons C10H16 of which one is a major constituent of wood turpentine …   New Collegiate Dictionary


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