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62638 Sigma-Aldrich

(+)-α-Longipinene

≥97.0% (sum of enantiomers, GC)

Synonym: (1R,2S,7R,8R)-2,6,6,9-Tetramethyltricyclo[5.4.0.02.8]undec-9-ene

  • CAS Number 5989-08-2

  • Empirical Formula (Hill Notation) C15H24

  • Molecular Weight 204.35

  •  MDL number MFCD00077624

  •  PubChem Substance ID 57651909

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Complex Molecules
assay   ≥97.0% (sum of enantiomers, GC)
optical activity   [α]20/D +25±1°, neat
refractive index   n20/D 1.493
bp   244-246 °C (lit.)
density   0.915 g/mL at 20 °C (lit.)
storage temp.   2-8°C
SMILES string   [H][C@@]12CC=C(C)[C@@]3([H])[C@@]1([H])C(C)(C)CCC[C@]23C
InChI   1S/C15H24/c1-10-6-7-11-13-12(10)15(11,4)9-5-8-14(13,2)3/h6,11-13H,5,7-9H2,1-4H3/t11-,12+,13+,15-/m1/s1
InChI key   HICYDYJTCDBHMZ-UKTARXLSSA-N

Description

Application

(+)-α-Longipinene can be used as a starting material for the synthesis of new terpenoids, (+)-(5S)-5,12-dihydroxy-α-longipinene, (-)-(5R)-5,12-dihydroxy-α-longipinene, and (+)-12-hydroxy-α-longipinen-5-one by oxidation reaction using Aspergillus niger as a biocatalyst. It can be oxidized using lead tetraacetate into tertiary alcohol, longi-cis-verbenol, longi-trans-verbenol, longi-cis-β-crysanthenol, longiverbenone, longi-trans- β -crysanthenol, 2 β,3 β -dihydroxylongipinane, 4 α,8-dihydroxy- α -Iongipinene, and 4 β,8-dihydroxy- α -longipinene.

Packaging

250 mg in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

RIDADR 
NA 1993 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
197.6 °F - closed cup
Flash Point(C) 
92 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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