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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
Catalytic acetylation of (+)-cedrol with heterogeneous catalyst H2SO4/SiO2 under solvent free conditions
Elvia R, et al.
Chemical Intermediates, 1(4), 196-201 (2015)
Oscar Mbare et al.
BMC infectious diseases, 19(1), 800-800 (2019-09-13)
Larviciding is an effective supplementary tool for malaria vector control, but the identification and accessibility of aquatic habitats impedes application. Dissemination of the insect growth regulator, pyriproxyfen (PPF), by gravid Anopheles might constitute a novel application strategy. This study aimed
Etsuro Hori et al.
Autonomic neuroscience : basic & clinical, 168(1-2), 88-92 (2012-02-22)
A previous study reported that when cedrol (odorant) is inhaled directly through the lower airway of the trachea, it decreases the sympathetic nervous activity and blood pressure in totally laryngectomized subjects (Umeno et al., 2008). In the present study, totally
D O Collins et al.
Phytochemistry, 56(5), 417-421 (2001-03-23)
Bioconversion of cedrol (1) with the Curvularia lunata was investigated in two different growth media. Five products were obtained in potato dextrose broth, whereas nine compounds were produced in a medium containing beef extract. Only three of the metabolites: 3beta-hydroxycedrol
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