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274399 Sigma-Aldrich

(−)-α-Pinene

99%, optical purity ee: ≥86% (GLC)

Synonym: (-)-alpha-Pinene, (1S)-(−)-α-Pinene, (1S,5S)-2-Pinene, (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene

  • CAS Number 7785-26-4

  • Empirical Formula (Hill Notation) C10H16

  • Molecular Weight 136.23

  •  Beilstein/REAXYS Number 1903790

  •  EC Number 232-077-3

  •  MDL number MFCD00064145

  •  eCl@ss 39011007

  •  PubChem Substance ID 24856583

  •  NACRES NA.22

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Properties

Related Categories Alkenes, Artemisia vulgaris, Asymmetric Synthesis, Boswellia carterii, Cell Biology,
Quality Level   100
vapor density   4.7 (vs air)
vapor pressure   ~3 mmHg ( 20 °C)
assay   ≥97.0% (GC)
  99%
optical activity   [α]20/D −50.0 to −46.0°, neat
optical purity   ee: ≥86% (GLC)
autoignition temp.   491 °F
refractive index   n20/D 1.465 (lit.)
bp   155-156 °C (lit.)
mp   -64 °C (lit.)
density   0.855 g/mL at 25 °C
SMILES string   CC1=CCC2CC1C2(C)C
InChI   1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
InChI key   GRWFGVWFFZKLTI-IUCAKERBSA-N

Description

General description

α-Pinene is a monoterpene used in industries like fragrance, pharmaceuticals, flavor, and cosmetics. It is a major component of pine oil and turpentine oil. Isomerization of α-pinene yields industrially important compounds like camphene, limonene, and p-cymene.

Application

(−)-α-Pinene can be used:
• To prepare chiral γ-amino alcohols, which are used as catalysts for the preparation of chiral 1-aryl-1-propanols using aromatic aldehydes.
• As a substrate in the study of its t-BuOOH mediated oxidation catalyzed by Co(II) complex.
• As a starting material for the synthesis of polyfunctionalized cyclobutane derivatives.

Packaging

25, 100 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Target organs 
Respiratory system
RIDADR 
UN 2368 3 / PGIII
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® B-DM

From our library of Articles, Sigma-Aldrich presents GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® B-DM
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® B-PM

From our library of Articles, Sigma-Aldrich presents GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® B-PM
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® G-DP

From our library of Articles, Sigma-Aldrich presents GC Analysis of α-Pinene Enantiomers on Astec® CHIRALDEX® G-DP
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

Peer-Reviewed Papers
15

References

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