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22135

Sigma-Aldrich

(+)-Cedrol

≥99.0% (sum of enantiomers, GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H26O
CAS Number:
77-53-2
Molecular Weight:
222.37
Beilstein:
2206347
EC Number:
201-035-6
MDL number:
MFCD00062952
UNSPSC Code:
12352212
PubChem Substance ID:
57647965
NACRES:
NA.22

Assay

≥99.0% (sum of enantiomers, GC)

form

solid

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catalytic acetylation of (+)-cedrol with heterogeneous catalyst H2SO4/SiO2 under solvent free conditions
Elvia R, et al.
Chemical Intermediates, 1(4), 196-201 (2015)
Kevin Hung et al.
Journal of the American Chemical Society, 138(51), 16616-16619 (2016-12-15)
Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50
Mitsuo Miyazawa et al.
Natural product research, 17(5), 313-317 (2003-10-07)
Microbial transformation of (+)-cedrol was investigated by using Staphylococcus epidermidis and found that stereospecific hydroxylation of (+)-cedrol occurred at the C-3 position to form (+)-(3S)-3-hydroxycedrol.
Daiji Kagawa et al.
Planta medica, 69(7), 637-641 (2003-08-05)
It has been reported that cedarwood oil has sedative effects when inhaled. In this study, we evaluated sedative effects of inhaled cedrol, which is a major component of cedarwood oil. Accumulative spontaneous motor activity was significantly decreased in the cedrol-exposed
L Hua et al.
Archives of biochemistry and biophysics, 369(2), 208-212 (1999-09-16)
A cDNA library was prepared from Artemisia annua, and a 129-bp fragment was amplified from this library using primers corresponding to sequences conserved in known dicot sesquiterpene synthases. A 1641-bp open reading frame that encoded a predicted protein 35-38% identical
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