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77429 Sigma-Aldrich

(R)-(−)-α-Phellandrene

≥95.0% (sum of enantiomers, GC)

Synonym: (−)-p-Mentha-1,5-diene, (R)-(-)-alpha-Phellandrene, (R)-5-Isopropyl-2-methyl-1,3-cyclohexadiene

  • CAS Number 4221-98-1

  • Empirical Formula (Hill Notation) C10H16

  • Molecular Weight 136.23

  •  Beilstein/REAXYS Number 2497824

  •  EC Number 224-167-6

  •  MDL number MFCD00062988

  •  PubChem Substance ID 57652697

  •  NACRES NA.22

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Properties

Related Categories Alkenes, Allium sativum (Garlic), Artemisia vulgaris, Asymmetric Synthesis, Boswellia carterii,
Quality Level   200
assay   ≥95.0% (sum of enantiomers, GC)
optical activity   [α]20/D −225±5°, c = 10% in diethyl ether
bp   171-174 °C (lit.)
density   0.844 g/mL at 20 °C (lit.)
storage temp.   2-8°C
SMILES string   CC(C)[C@H]1CC=C(C)C=C1
InChI   1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m1/s1
InChI key   OGLDWXZKYODSOB-SNVBAGLBSA-N

Description

General description

(R)-(-)-α-Phellandrene is a monoterpene derivative.

Application

(R)-(-)-α-Phellandrene undergoes [4+2] cycloaddition with 2-naphthyl acetylenecarboxylate to form a chiral diene, which can act as a ligand for the rhodium-catalyzed asymmetric addition reactions. It may be used to synthesize (1S,5R)-5-(1-methylethyl)-2-methylidene-3-cyclohexen-1-yl hydroperoxide, which on reduction forms trans-yabunikkeol.

Packaging

1, 5 mL in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 2319 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
107.6 °F - closed cup
Flash Point(C) 
42.0 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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