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22135 Sigma-Aldrich

(+)-Cedrol

≥99.0% (sum of enantiomers, GC)

Synonym: (1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol

  • CAS Number 77-53-2

  • Empirical Formula (Hill Notation) C15H26O

  • Molecular Weight 222.37

  •  Beilstein/REAXYS Number 2206347

  •  EC Number 201-035-6

  •  MDL number MFCD00062952

  •  PubChem Substance ID 57647965

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Cell Biology, Chemical Synthesis, Chiral Building Blocks, Complex Molecules,
Quality Level   100
assay   ≥99.0% (sum of enantiomers, GC)
optical activity   [α]20/D +10.5±1°, c = 5% in chloroform
bp   273 °C (lit.)
mp   82-86 °C
  86-87 °C (lit.)
SMILES string   C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)O
InChI   1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
InChI key   SVURIXNDRWRAFU-OGMFBOKVSA-N

Description

General description

(+)-Cedrol is a crystalline hydrated product of α-cedrene, which is a sesquiterpene found in cedar-wood oil. It can be used as a fragrance ingredient in cosmetics, shampoos, and soaps as well as in non-cosmetic products such as cleaners and detergents. (±) Cedrol can be synthesized by intramolecular Diels-Alder reaction of alkyl cyclopentadiene.

Application

(+)-Cedrol can be used as a starting material for the preparation of cedryl acetate by acetylation using acetic anhydride in the presence of an acid catalyst. It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
PB7728666
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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